Discover Charming Cottages in Key West, FL

Located in Key West, this Florida adult-only inn offers complimentary, light continental breakfast and free Wi-Fi access. Duval Street is 2 minutes’ drive from the property and The Ernest Hemingway Home and Museum is 3 minutes’ drive away. A TV, telephone, and a refrigerator are included in all rooms at Key West’s Simonton Court. A balcony or patio is also featured in addition to an private bathroom. The gallery photos show examples of different bedrooms in each category. Guests can enjoy swimming any one of the 4 on-site outdoor pools, use the bicycle hire, or relax in the garden. Kindly note that private parking is available upon request as there are limited spots. Please inform the property in advance. A concierge service and daily maid service are also available. The Southernmost Point of the continental United States of America is 5 minutes’ drive from the inn. Mallory Square is 2 minutes’ drive from the property, and Smathers Beach is 2.6 mi away.

- "Great location, accommodating staff, beautifully landscaped." - "Must stay!" - "We loved pretty much everything!" - "Fantastic place will be recommending it should any of our friends be travelling this way." - "A lovely stay in Key West" - "Was afabulous couples get away spot. Quiet, understated luxury close to the Duvall party scene." - "AWESOME!" - "Lovely property!" - "Will return."

Located in Key West, this welcoming cottage lets you experience it all. Florida Keys Beaches is just steps away and Clarence S. Higgs Memorial Beach Park is within an easy 12-minute walk, so leave your car at the property, which offers onsite parking.

After you return, you can unwind at the beach, chill by the outdoor pool, or sip a drink on the balcony. For a change of scenery, come inside and enjoy the free WiFi and TV.

As you settle into this 2-bedroom, 2-bathroom rental, you'll find a living room, air conditioning, and a ceiling fan. Prepare a home-cooked meal in the kitchen, complete with an oven, a stovetop, and a refrigerator, as well as a coffee maker and cookware.

- "The views and facilities are excellent!! The gutters falling off during a rainstorm were spectacular. The no see-ums were abundant this time of year (spring). We were bitten badly. We didn't realize that no see-um bites would hurt so much and last so long! But overall our stay was fantastic! " - "Loved the separateness of the two bedrooms and two baths. Was beginning to be a little dated but actually loved the nostalgia. Beds were sooo comfortable, didn’t want to leave! lol discovered a good place to eat the night before we left, right down the street. Snatchers beach was within walking distance. Would stay again."

Located right off Duval Street, the Andrews Inn and Garden Cottages are less than 5 minutes’ walk from various dining and entertainment options. Guests can enjoy free WiFi and an outdoor pool. A flat-screen TV and an iPod docking station are featured in each classic room at this Key West bed and breakfast. Guests will also enjoy the convenience of a refrigerator in their room. Rooms also have a clock radio with auxiliary cables. Concierge services are located on site, as are luggage storage, beach towels, and on-site maid and bike hire services. A complimentary poolside happy hour is available and guestrooms located in the Main Inn offer a hot breakfast. The Ernest Hemingway Home and Museum is less than 5 minutes’ walk from the property and The Southernmost Point of the Continental United States and Mallory Square are just 0.5 miles away.

- "Attentive, continental breakfast was so appreciated." - "Perfect" - "Great location, amazing Staff, very well decorated place and good breakfast!" - "Our favourite stay in Key west!" - "My forever Key West Destination" - "Wonderful!!!!!" - "Beautiful" - "A fantastic 3 day getaway in a great location with an awesome host!" - "We love the Andrews!"

Located in Key West, this welcoming cottage lets you experience it all. There's convenient onsite parking, so you can leave your vehicle behind and head out to Duval Street and Key West Cemetery, just a short walk away.

Relax by the communal pool or sip a drink on the porch or lanai of this cottage, which also features a BBQ grill. For a change of scenery, come inside and enjoy the free WiFi and TV.

As you settle into this 1-bedroom, 1.5-bathroom rental, you'll find a living room, a sofa bed, air conditioning, and a ceiling fan. Bathroom amenities include a hair dryer and towels. The kitchen is equipped with an oven, a stovetop, and a refrigerator, as well as a coffee maker, a microwave, and cookware. And thanks to the washer and dryer, you'll even be able to travel light.

- "The unit had fun and stylish decor. Bed was comfy and I’m picky. The steeps are a challenge- always forgetting there is one more step. Was concerned about the noise in the back from a restaurant or bar- but when doors closed you can’t hear it. And there is no noise later in the evening. One suggestion- some nightlights for the night for Safety. We will be back. Great experience " - "Great little area of cottages with decent sized pool. Each cottage is a different layout and privately owned. Quiet and safe area, but close enough to walk/bike to just about everything. Rooms and common areas were very clean. The only downsides were the steep stairs up to the bedroom and no counter space in bathrooms. Other than that, it was a great stay!"

Atocha Cottage by Brightwild is located in Key West, just a 6-minute walk from Key West Aquarium and 500 yards from Mallory Dock. This apartment provides air-conditioned accommodations with a patio. The property is a 4-minute walk from Simonton Street Beach and within half a mile of the city center. With free Wifi, this 2-bedroom apartment offers a cable TV and a kitchenette with a microwave and fridge. Towels and bed linen are featured in the apartment. The accommodation is non-smoking. Guests can enjoy the outdoor swimming pool at the apartment. Popular points of interest near Atocha Cottage by Brightwild include Fort Zachary Taylor State Park Beach, South Beach, and Mallory Square. The nearest airport is Key West International Airport, 2.5 miles from the accommodation.

Child Friendly • Pool • Pet Friendly • Internet • Air Conditioner • Other • Security/Safety

Located in Key West, this welcoming cottage lets you experience it all. There's convenient onsite parking, so you can leave your vehicle behind and head out to Duval Street and Key West Lighthouse and Keeper's Quarters Museum, just a short walk away.

As you settle into this 2-bedroom, 2.5-bathroom rental, you'll find a living room, air conditioning, a ceiling fan, and concierge services. Connect to the free WiFi, or get cozy in front of the digital TV (streaming services available). Bathroom amenities include free toiletries, towels, and toilet paper. The kitchen is equipped with an oven, a stovetop, and a refrigerator, as well as a coffee maker and cookware. And you can even travel light because you'll have a washer/dryer. Other amenities include bed sheets, tour/ticket assistance, and heating.

- "The living room furniture and mattresses are not the most comfortable. Worn. Mattresses in small bedroom need replacement. Air conditioner does not reach small bedroom. "

Cottage by the Pool by AvantStay w Balcony BBQ Shared Pool Month Long Stays Only offers accommodations in Stock Island, 5 miles from Ernest Hemingway Home and Museum and 5 miles from Duval Street. This vacation home features air-conditioned accommodations with a patio and free Wifi. Mallory Dock is 5.4 miles away and Mallory Square is 5.4 miles from the vacation home. The vacation home features 2 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom with a hair dryer. Towels and bed linen are offered in the vacation home. The property has an outdoor dining area. Cottage by the Pool by AvantStay w Balcony BBQ Shared Pool Month Long Stays Only conveniently has an outdoor pool. Southernmost Point is 5.2 miles from the accommodation, while Key West Aquarium is 5.4 miles from the property. Key West International Airport is 2.5 miles away.

Security/Safety • Child Friendly • Air Conditioner • View • Pool • Sports/Activities • Internet

Located in Key West, this welcoming cottage brings it all within your reach. With the property's convenient onsite parking, you'll be ready to make the quick 5-minute drive to Duval Street or the 2-minute drive to Florida Keys Beaches.

As you settle into this 3-bedroom, 2-bathroom rental, you'll find air conditioning and a ceiling fan. Enjoy the free WiFi and TV. The kitchen is equipped with an oven, a stovetop, and a dishwasher, as well as a microwave, cookware, and spices. Other amenities include bed sheets, an ironing board, and housekeeping.

Internet • Child Friendly • Security/Safety • Laundry • Air Conditioner • Other • Parking • Tv • Kitchen

The Conch-Out Cottage is located in Key West, just a 14-minute walk from Key West Aquarium and 0.8 miles from Mallory Dock. With pool views, this accommodation features a terrace and a swimming pool. The property is 200 yards from the city center and a 11-minute walk from South Beach. The air-conditioned vacation home is composed of 1 separate bedroom, 2 living rooms, a fully equipped kitchen with a dishwasher and oven, and 2 bathrooms. Towels and bed linen are offered in the vacation home. There's also a seating area and a fireplace. There is an on-site restaurant. Guests at the vacation home will be able to enjoy activities in and around Key West, like cycling. A children's playground is also available for guests at The Conch-Out Cottage. Popular points of interest near the accommodation include Ernest Hemingway Home and Museum, Duval Street, and Southernmost Point. Key West International Airport is 2.5 miles from the property.

Fireplace/Heating • Restaurant • Guest Services • Child Friendly • Sports/Activities • Balcony/Terrace • Laundry • Air Conditioner • View • Pet Friendly • Security/Safety • Pool

Tropical Cottage is a quintessential 1930s-era Conch bungalow, lovingly renovated with contemporary island elegance. The sage-green exterior blends Caribbean and Victorian influences: crisp white trim, abundant windows, and black Bahamian shutters. This charming cottage is set back from the street and shaded by gardens, mature palms, and gumbo limbo trees in a quiet, upscale, gated enclave of six historic Old Key West vacation rentals. The spacious pea-gravel courtyard boasts tropical landscaping, coral and rock hardscaping, and stone walkways leading to the shared pool area.
Sip Cafe Cubano on the private back deck as Caribbean breezes rustle palm fronds. Prepare a home-cooked meal in the modern kitchen. Dine alfresco when nights are fragrant with jasmine and frangipani. Relax poolside with a Margarita. The central common area, with a pool, picnic tables, and gas grill, is shared by guests of this upscale enclave. There’s also a shared laundry area with commercial washers & dryers.
Stroll to great seafood, fine dining, beaches, and iconic attractions like the KW Butterfly & Nature Museum, Southernmost Point, Higgs Beach, and West Martello Tower. After a day at the beach, shower off in either of two hot-water outdoor showers. Street parking is available. Tropical Cottage is ideal for families, groups of friends, couples, and snowbirds. The home has an all-new water filtration system.
Living:
The bright, contemporary living space has polished, rich wood flooring, which imbues a warm island vibe. The driftwood gray interior pops with accents of white and cream. Relax on the plush sofa or armchairs to socialize, read, or stream your favorite shows on the wall-mounted SmartTV with Roku. Stylish coffee tables, lamps, a ceiling fan, and large windows enhance the space. This living space has French doors, which open to a private deck with alfresco dining.
Just off the primary bedroom is a sunroom/breakfast nook with extra living space. This bonus room offers multi-purpose space (TV lounge/office/kid or teen space) and has a private entrance from the courtyard. This cozy room has an authentic island vibe with colorful mosaic floors, a wall of windows, a ceiling fan, and an air conditioner. Relax on the key-lime colored loveseat to stream movies on the Smart TV. The dinette can seat two or more.
Kitchen/Dining:
The open-concept kitchen/living space makes for easy entertaining and socializing. The sleek, fully-stocked modern kitchen has cream-colored, custom hardwood cabinets, granite countertops, and stainless appliances, including a glass-top electric stove, oven, microwave, dishwasher, full-size fridge, and farmhouse-style island sink. Prepare a tropical feast after a day at the beach!
Open the French doors for a seamless indoor/outdoor entertaining space. The deck dining table has an adjustable umbrella. There are poolside picnic tables in the common area and a dinette in the breakfast nook.
Bedrooms/Baths:
Tropical Cottage has two bedrooms and two bathrooms. The living room has a twin-size sleeper sofa. Both air-conditioned bedrooms have tile floors and ceiling fans. Both sparkling-clean, beautifully remodeled bathrooms have water-saving toilets, toiletries, and hair dryers.
The primary bedroom has a King bed, matching nightstands with lamps, a bureau, a closet, and an ensuite bathroom. This primary bathroom has a walk-in, glass door shower with a rain showerhead and hand-held shower wand. There’s an oversized, single-sink white granite vanity.
The guest bedroom has two twin beds, a nightstand with lamp, a bureau and access to a hallway bathroom with a glass door shower and an oversized, single-sink white granite vanity.
Two refreshing outdoor showers offer rustic tropical serenity, perfect for rising off the sand or chlorine after a day of island fun.
Outdoor Amenities:
A tall exterior fence, lush gardens, mature trees, and gardens provide privacy, security, and a peaceful, tropical ambiance. Enjoy a private dining space on your fenced back deck. This shaded dining space seats six.
A garden courtyard and whitewashed fence buffer your private hideaway from a central common area. Cool off in the sparkling blue swimming pool, or doze poolside on a cushioned lounge chair. This swimming pool will delight families, children, the very young, and the young at heart. The poolside deck features a gas grill and two wrought-iron picnic tables with seating for eight or more. Gather for an afternoon cookout in paradise! Mature palms, mango trees, and vibrant bougainvillea shade the pool deck.
Since laundry never sleeps (even when you're on vacation), the common area offers a laundry shed with two commercial washers and two commercial dryers.
Discover the ultimate amenity: stroll just two blocks to Higgs Beach. Dip your toes in the emerald ocean. Collect seashells and savor serene Caribbean sunsets in pink, violet, and gold hues. Park your car in shaded street parking spots out front. Stroll or bike to attractions.

The Neighborhood:

The proximity of Tropical Cottage to the Casa Marina Hotel and the beautiful beaches adds to the appeal, making it a perfect blend of history, culture, and coastal living. Picturesque south island streets are lined with beautifully preserved Conch-style homes, each exuding character and charm. Lush, tropical landscaping adds to the serene atmosphere, making every walk or bike ride a delightful experience.

A car is not necessary on the island. Make the green choice. Park out front or along shaded side streets and enjoy the island on foot, by bicycle, scooter, trolley, or bus. The island trolley stop is one block away. The Duval Loop City bus stop is four blocks away.
Stroll .07 miles to The Ernest Hemingway Home and Museum, which offers a fascinating glimpse into the life of one of America's greatest writers. Enjoy the diverse culinary scene with various restaurants, cafes, and bars offering everything from fresh seafood to classic Cuban cuisine. Local favorites such as Blue Heaven, Louie’s Backyard, and Sloppy Joe’s are within easy reach, providing unforgettable dining experiences.
Don't miss the chance to explore West Martello Tower during your stay! Just a 10-minute walk or a quick 3-minute bike ride from Tropical Cottage, this hidden gem is a tropical garden paradise on the site of a historic Civil War fort. The gardens, maintained by the Key West Garden Club, are open to the public.
Higgs Beach, approximately 0.5 miles (a 10-minute walk or a 3-minute bike ride), is the closest beach. Enjoy crystal-clear waters, perfect for swimming or snorkeling. The nearby White Street Pier offers panoramic sea views and excellent fishing opportunities.
Approximately 1.5 miles away, Smathers Beach is Key West’s largest public beach. This two-mile stretch of sugary sand is ideal for sunbathing, beach volleyball, and water sports such as kayaking, paddleboarding, and windsurfing.
Fort Zachary Taylor Historic State Park Beach, approximately 2 miles away, offers natural beauty and historical intrigue. Visitors and locals gather here and at Mallory Square to celebrate each and every exquisite island sunset.
Seeking family-friendly activities or rainy-day excursions? Check out the Key West Aquarium, the Butterfly and Nature Conservatory, The Shipwreck Treasure Museum, and the Lighthouse and Keepers Quarters Museum. Nightlife and live music abound in Key West! Take in a show at the Tropic Cinema. Catch a live band at the Green Parrot.

- "The property was in a great location! Parking across the street. We rented bicycles to get around! The pool was refreshing and right out the back door! Great place to stay!" - "LOVED THE COTTAGE / THE LOCATION AND PROPERTY MANAGEMENT" - "Took my Mom and sister and we had the best time and perfect place for girls." - "Good parking out on the street, very short walk to both beautiful South Beach and Duval Str.. We couldn't have had a better place to stay in Key West."

Boat House by AvantStay Character Cottage Central Location w Shared Pool Month Long Stays offers accommodations in Key West, a 15-minute walk from Mallory Square and 0.9 miles from Southernmost Point. The air-conditioned accommodation is a 13-minute walk from Simonton Street Beach, and guests can benefit from on-site private parking and complimentary Wifi. The property is 500 yards from the city center and a 5-minute walk from Duval Street. Opening onto a patio, the vacation home consists of 1 bedroom. Providing a terrace with pool views, this vacation home also offers a TV, a well-equipped kitchen with a dishwasher, an oven, and a fridge, as well as 2 bathrooms with a shower and a hair dryer. The property has an outdoor dining area. The vacation home conveniently has an outdoor pool. Popular points of interest near Boat House by AvantStay Character Cottage Central Location w Shared Pool Month Long Stays include Ernest Hemingway Home and Museum, Key West Aquarium, and Mallory Dock. Key West International Airport is 2.5 miles away.

Parking • Security/Safety • Internet • Fireplace/Heating • Child Friendly • Air Conditioner • Pool • View • Balcony/Terrace

This memorable cottage is the perfect home base for your trip to Key West. With 2 bedrooms, including 1 king bed and 1 queen bed, it offers a comfortable and cozy stay for guests. The property features essential amenities like a washer/dryer, AC/heating, fully equipped kitchen, bedding, towels, and WiFi. The bathroom is equipped with basic soap, shampoo, towels and a hair dryer. There is a large shared pool area. Our cottage is designed to make your vacation one to remember. So come and experience the gorgeous charm of this awesome Key West cottage. Your vacation awaits!

- "Lovely, recently renovated home in a lovely community of small Key West homes with a shared pool. It was also very quiet and comfortable and close to everything. "

Offering a heated outdoor pool, this boutique Ella's Cottages is located in Old Town Key West 2 minutes' walk from Duval Street. Free WiFi and a poolside continental breakfast are provided. A flat-screen cable TV, an en suite, and hardwood floors and furnishings are standard in all rooms and suites. All rooms have a mini fridge. Both rooms and suites include access to a tropical garden. The guest house is 1476 feet from Ernest Hemingway Home and Museum and 15 minutes' walk from the Sunset Pier. Higgs Beach is 1.2 mi away.

- "Hot, relaxing and a lot of laughs" - "Pleasant and peaceful" - "Wonderful family time" - "Historic charm and pampering" - "Wonderful property, quaint rooms and friendly staff" - "wonderful" - "Perfect quiet spot but still super close to all the old town locations and restaurants. Would 100% recommend" - "Could not have had a better time than we had" - "Just perfect, we are going come back" - "Ella’s Cottages was walkable to so much! Beautiful property."

WELCOME TO PINEAPPLE COTTAGE!

The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town Key West. It offers a private pool and is just half a block away from Duval Street, making it an ideal tropical oasis for your vacation.

As you enter the cottage, you'll step onto a deck overlooking the backyard, where you'll find the inviting private pool, a charcoal grill, and various seating and lounging areas surrounded by lush tropical landscaping, ensuring your privacy and creating a serene atmosphere.

Inside, the cottage features an open living area and kitchen space, perfect for easy flow and entertaining. The living area is equipped with a fully loaded entertainment system, including cable TV, a sound system, CD player, and DVD player. You'll also find board games for some indoor fun, whether in the living room or at the outdoor table. The kitchen is fully equipped and includes a breakfast bar with bar chairs, providing a convenient division from the couch and comfortable viewing chairs in the living room.

On the first level of the cottage, there is a full bathroom and a hidden bedroom tucked away to the right of the kitchen. This bedroom features a queen-size bed and all the amenities necessary to ensure a comfortable stay. You can choose to keep the curtains and blinds closed for a peaceful sleep-in or open them up to let the tropical sun awaken you for an adventurous day.

The second floor of the cottage offers another spacious living area with cable TV, a large comfortable sofa, and chairs for relaxation. The master bedroom on this level boasts a king-size bed and an en-suite full bathroom. Additionally, the washer and dryer are conveniently located in this bathroom for the guests' use.

The backyard of the Pineapple Cottage is a true haven. With its sparkling pool, grill, and dining areas, you have everything you need to enjoy meals at home while entertaining and making the most of your vacation. The cottage location in the Old Town district allows you to easily walk to Duval Street, where you'll find a variety of shopping, beaches, and restaurants in close proximity.

Overall, Pineapple Cottage offers top-of-the-line amenities and comfort, ensuring a delightful and enjoyable stay in Key West.

Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know.

**Pool heat is optional at $25 a day.**

- "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This place is amazing. You can’t beat the location, walk to everything in minutes. The house and pool area were great. Definitely will be my go to place to rent." - "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Perfect location. Management was great. Pool was relaxing."

Just a 5-minute walk from Key West Aquarium and 500 yards from Mallory Dock, New The Cottage at James House features accommodations in Key West with a garden. This vacation home offers air-conditioned accommodations with a patio. The property is 0.4 miles from the city center and a 6-minute walk from Simonton Street Beach. With free Wifi, this 1-bedroom vacation home features a cable TV, a washing machine, and a fully equipped kitchen with an oven and microwave. Towels and bed linen are offered in the vacation home. For added privacy, the accommodation features a private entrance. Guests at the vacation home can enjoy cycling nearby, or make the most of the outdoor pool. Popular points of interest near New The Cottage at James House include Mallory Square, Duval Street, and Ernest Hemingway Home and Museum. Key West International Airport is 2.5 miles from the property.

- "Great Location" - "Great stay once the cottage was located."

WELCOME TO CONCH COTTAGE!

In the 20th century many residents of Key West began referring to themselves as “Conchs”, now this term generally applied to all residents of Key West. This vacation home is called Conch Cottage because it encompasses the heart of the Key West life style.

In the heart of Old Town with traditional architecture, this home serves as a perfect luxury and vacation. This home is exactly what you would imagine! From the ginger bread features to the porch seating area and colorful paint, this is a perfect place to people watch and relax at any hour of the day. Conch Cottage is a one bedroom, one bath home with a full kitchen and back deck. This rental is ideal for a couple or single guest.

Conch Cottage is fully furnished and features a completely renovated, fully equipped kitchen with stainless steel appliances and a BOSCH stackable washer and dryer. The living and dining areas are open concept. There is a flat screen, cable TV and couch. The open space allows full view of the French doors leading to your private rear deck.

The bedroom has a queen bed and a door to the private back deck. You can close the curtains for privacy or let the sunshine come through.

The rear deck has all the amenities you could need. The space has a lounging area, an outdoor seating area with an umbrella, hot tub, and a grill. This can serve as an outdoor dining area. This deck is the ultimate place to relax, entertain, grill and live like a local! Another bonus is the private, outdoor shower. You can slip away, allowing the tropical breeze in with no worries, there is complete privacy.

If you want to take a swim, Key West has a community center with a huge community swimming pool and a deck overlooking the Atlantic Ocean. There is also a park next door to the pool, you may also want to take a bike ride in the Truman Annex, or ride to the tree-lined beaches of historic Ft. Zachary Taylor.

Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know.

Conch Cottage is a non-smoking home.
Please Note: This property does not have assigned parking.

- "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: First off, Angie with Preferred Properties is absolutely incredible and went above and beyond to accommodate my husband and I when we found ourself in need of last minute accommodations. I really can’t say enough about how fantastic she was! Outside of that, the home had absolutely everything we needed and was in the perfect location to walk to everything. It has an amazing intimate fenced in back yard with a great jacuzzi. If you are thinking of booking, think no more, BOOK IT!"

Atocha Cottage - Harbor Walk Hideaways offers accommodations in Key West, a 5-minute walk from Mallory Dock and 600 yards from Mallory Square. The apartment provides an outdoor pool and free Wifi. The property is half a mile from the city center and a 4-minute walk from Simonton Street Beach. The air-conditioned apartment is composed of 2 separate bedrooms, a living room, a fully equipped kitchenette with a microwave and fridge, and 1 bathroom. Towels and bed linen are provided in the apartment. The accommodation is non-smoking. Popular points of interest near Atocha Cottage - Harbor Walk Hideaways include Fort Zachary Taylor State Park Beach, South Beach, and Key West Aquarium. Key West International Airport is 2.5 miles away.

- "Great location, nice decor, but needs a little more attention."

A Historic Cigar-Makers Conch Home, privately owned by a native hospitable family in the heart of Downtown, a few minutes walk from Duval St. Accommodates 1-2 couples. Your car will be safe in this parking spot, nowhere near the street. The Cottage is set back from the sidewalk so you are not subjected to traffic noises.

Note two things:
1. The price listed is for 2 guests only. There is an additional charge of $75/night for an additional guest.

2. The cottage is set back from the street but nearby at Hank's there is live music...luckily
as of around 10.18.23 - their music is now set further back from us! The music ends at midnight.

Fully Equipped Kitchen with Dishwasher
Full Size Refrigerator and Stove
1 King Bed, 1 Queen Bed
Central Air Conditioning
TVs with Premiere Cable
Full Size private Washer & Dryer on premises. For use by tenant and this tenant only.
Free Internet
Parking: Off-Street, 1 parking space, only to be used for those staying at the cottage.
Adults only. No Pets. No Smoking. No raw fish in the refrigerator or freezer.

- "Super nice vacation house - very close to Duval & easy walking distance to the Bight." - "Awesome place. Owners very accommodating. Very clean. We will be back. Definitely recommend it." - "This location is great and the house was clean and had everything we needed. It was easy to communicate with the property manager. Thank you!" - "Marcela is a gracious host! The place was immaculate when we arrived. The cottage was perfectly comfortable and location is the best for walking around the historic district of Key West! We’ll certainly be back!!!"

Pilar Cottage - Harbor Walk Hideaways offers accommodations in Key West, a 12-minute walk from Duval Street and 0.9 miles from Ernest Hemingway Home and Museum. This property offers a heated pool and free Wifi. The property is a 4-minute walk from Simonton Street Beach and within half a mile of the city center. The air-conditioned apartment is composed of 1 separate bedroom, a fully equipped kitchenette with a microwave and a fridge, and 1 bathroom. Towels and bed linen are featured in the apartment. The accommodation is non-smoking. Popular points of interest near the apartment include Key West Aquarium, Mallory Dock, and Mallory Square. Key West International Airport is 2.5 miles away.

Pool • Child Friendly • Internet • Security/Safety • Pet Friendly

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

Don't miss an exceptional opportunity to spend your Key West stay on the grounds of an incredible estate property in the most ideal Old Town location you could imagine. This two-story guest cottage offers many of the essentials and comforts of a luxury hotel plus the added benefits of an in-home washer & dryer, a private patio with a jacuzzi/hot tub, and your own BBQ grill for cooking the day's catch. Whether you are two couples, a family, or a few friends traveling together you'll find opportunities for both privacy and togetherness in this unique vacation home.

DARLING OF DUVAL and Last Key Realty's Five-Star In-Home Guest Services are the perfect combination to create the five star hospitality typically associated with luxury hotels - all in the Old Town location of your dreams.

THE LOCATION...

The drop pin on the map says it all: this estate is right in the thick of the best restaurants, nightlife, shopping, and sightseeing of Key West. This gated estate opens up onto one of the legendary corners of the island but is built back far enough from the street to minimize noise from businesses or passersby. From your balcony you might never know you are just a stone's throw from the best bars and restaurants of Duval Street. You'll also be within half a mile of Fort Zachary Taylor State Park, home to Key West's remarkable state park beach and the family friendly waterfront park. You'll be able to reach all of your favorite spots on foot, but this home does include off street parking for one vehicle or electric car/golf cart as well as space for mopeds or bicycles. When aiming for the true Old Town Key West location, it simply doesn't get any better than this.

THE ACCOMMODATIONS...

This unique guest cottage consists of two studio-style suites, one on each floor. Each floor features beautiful sliding glass doors that create an open-air feeling on breezy days. The two floors are connected by an external staircase.

• First Floor Suite: King bed, large walk in shower, en-suite bathroom, kitchenette (blender, coffee maker, hot plate, microwave) sitting area, SMART TV, washer & dryer.

• Second Floor Suite: King bed, large walk in shower, en-suite bathroom, kitchenette (blender, coffee maker, hot plate, microwave) sitting area, SMART TV, balcony.

YOUR PRIVATE PATIO and JACUZZI...

Outside the first-floor suite is a lovely private patio with outdoor dining for four, a comfortable outdoor lounge area, and a BBQ Grill perfect for cooking today's catch. The jacuzzi is all yours and can be left cool on a hot day or heated up in the winter months. Enjoy a happy hour cocktail in your jacuzzi spa before heading out on Duval for the evening.

Note: There is a pool on this owner-occupied estate property but it is not offered for guest use.

ALL LAST KEY VACATION HOMES INCLUDE:

• Washer and Dryer
• A/C
• Ceiling Fans
• Flat Screen Cable TVs
• Fully-Equipped Kitchenette
• Basic stock of spices
• Starter supply of paper products
• Starter set of cleaning products
• Linens and Towels provided
• Wireless high-speed Internet access and full cable is included
• Full Time Concierge Service

In addition, this fully stocked home also includes, but is not limited to the amenities on this list:

• Landscaped Private Patio with Jacuzzi Spa/Hot Tub
• Propane BBQ grill
• Off-Street Parking

Other notes:

• Interim housekeeping provided upon request
• This guest cottage is located on a private estate with full time owner occupation. Guests are prohibited from use of the main swimming pool on property.
** Owner has dogs on property in the main house
** This property will accommodate up to 4 adults
** No Pets Allowed
** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

- "Beautiful property and surprisingly quiet, given that it is right on Duval Street. The property manager was also very helpful and responsive. We’d definitely go back!" - "This is an amazing property, perfectly situated for the major key west attractions. Can’t wait to return." - "Last Key Realty is very helpful, informative and professional. Use them! The house was clean and comfortable. Very nice location!! We will stay again." - "This property is spectacular. The owners were amazing and hope to stay here again soon."

Offering air-conditioned rooms in the Downtown Key West district of Key West, Old Town Cottage is a 16-minute walk from Southernmost Point. The apartment has access to a restaurant. The property is a 13-minute walk from South Beach, and within half a mile of the city center. At the apartment complex, each unit is equipped with a desk, a flat-screen TV, a private bathroom, bed linen, and towels. An oven, a microwave, and fridge are also provided in the kitchen, as well as a coffee machine. The rooms are equipped with heating facilities. Guests at the apartment will be able to enjoy activities in and around Key West, like cycling. Popular points of interest near Old Town Cottage include Ernest Hemingway Home and Museum, Duval Street, and San Carlos Institute Casa Cuba. Key West International Airport is 1.9 miles away.

Guest Services • Restaurant • Fireplace/Heating • Sports/Activities • Security/Safety • Child Friendly • Laundry • Air Conditioner

Located in The Colony, a secluded, gated enclave just steps from Duval Street, Colony Sunset is a colorful and relaxing retreat. Walk up the flagstone path and enter the home through the vivid and cheerful living space, accented with cerulean blue walls and splashes of tropical art. A vaulted ceiling with exposed beams and huge transom windows that extend all the way to the tip of the roof add a bright and airy feeling to the cozy space. Just through the French doors lies a private deck for sunning, relaxing and al fresco dining.

The fully appointed kitchen is attached to the living area and features a sit-down bar, charming open shelving and a bright color scheme.

The bedroom is painted in soothing blue tones and features cathedral ceilings, a king size bed, and flat screen television.

Just outside the front door is a porch with Adirondack chairs for enjoying a morning Cuban coffee or a twilight glass of wine amongst the palm trees. The huge Colony swimming pool, which is shared with other residents, is located just steps away. Beaches, shopping, and award-winning restaurants are just a short walk or bike ride from your front door.

If you are staying with a large group, please note that Rent Key West Vacations has two other similar properties to rent within this compound- Colony Calypso and Colony Poolside.

Bedding: 1 King, 1 sleeper sofa (full)

Pet friendly- under 40 pounds. Additional fees apply.

Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter the home through the serene and inviting living space, accented with blue and white decor, wood floors and pops of color from nautical-themed accents and artwork. A vaulted ceiling with exposed beams and huge transom windows that extend all the way to the tip of the roof add a bright and airy feeling to the cozy space.

The fully appointed kitchen is attached to the living area and features a generous sit-down bar and charming open shelving. Through the French doors lies a private deck for sunning, relaxing, grilling and al fresco dining.

The bedroom is accented with wainscoting and features cathedral ceilings, a king size bed, and flat screen television.

Back outside the front door is a porch with Adirondack chairs for enjoying a morning Cuban coffee or a twilight glass of wine amongst the palm trees. The large Colony swimming pool, which is shared with other residents, is located just steps away. Beaches, shopping, and award-winning restaurants are just a short walk or bike ride from your front door.

If you are staying with a large group, please note that Rent Key West Vacations has two other similar properties to rent within this enclave - Colony Sunset and Colony Calypso.

Bedding: 1 king, 1 sleeper sofa

Parking: There is a small parking lot for cottage guests and available on a first come first parked basis. If the lot is full, there is on-street parking right on Oliva Street and on surrounding side streets and lanes.

- "Great location. a short walk away from all major attractions. Clean and well kept quarters." - "The interior of the accommodation was exactly what we expected from the website. The exterior was a bit confusing as we thought it was going to be a small cottage with the exterior of the house on the website. The pool was immaculate and property well kept. Convenient location to downtown Duval and local grocery store. Overall we had an excellent vacation in Key West. Thank you!"

Garden of Eden Cottage offers accommodations in Key West, 1.4 miles from Key West Aquarium and 1.4 miles from Mallory Dock. This vacation home offers air-conditioned accommodations with free Wifi. The property is a 12-minute walk from Higgs Beach and within 0.6 miles of the city center. The vacation home features 1 bedroom, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom with a hair dryer. Towels and bed linen are featured in the vacation home. For added privacy, the accommodation features a private entrance. Guests can enjoy the outdoor swimming pool at Garden of Eden Cottage. Popular points of interest near the accommodation include Ernest Hemingway Home and Museum, Southernmost Point, and Duval Street. Key West International Airport is 1.9 miles away.

Internet • Child Friendly • Security/Safety • Laundry • Pool

Location is ideal for this wonderful one bedroom retreat. A lush, inviting compound created so owners and guests could enjoy the shared tropical outdoor spaces. This location offers a convenient walk to Mallory Square, the Historic Seaport and all other attractions and activities that Key West has to offer. All of the action of Duval street including Sloppy Joe's, Hog's Breath and The Bull is just around the corner yet when you return "home" you return to a peaceful get away from it all atmosphere. At this location you do not need a car as all attractions, activities and beaches of Old Town are walking distance! (There is no parking provided)

This tropical cottage is designed for relaxation with bamboo accents and serene colors. The cottage has beautifully unique and original Cuban tile floors throughout, a king-sized bed, one spa-like bath with over-sized walk-in shower, washer and dryer in the unit. There is also a private courtyard with deck, opening from the living room and bedroom with outdoor furniture perfect for working on your tan and outdoor enjoyment. The common area of the compound has a shared pool, sunning and garden area.

Keywords: House

- "We enjoyed our stay so much!! It was a perfect getaway for us!!" - "Excellent!" - "Was wonderful, just wonderful. Property and location is just perfect. We highly recommend." - "This is the perfect getaway spot in Key West. You are a block off Duval, right behind Fogarty's and Sloppy Joes. You can walk to where the action is or lay by the pool in your own private jungle hideout. We would absolutely stay here again." - "Very nice and clean cottage! Perfect location in walking distance to everything. Will return"

Coconut Cottage offers accommodations in Key West, a 17-minute walk from Key West Aquarium and 0.9 miles from Mallory Dock. Guests staying at this vacation home have access to a patio. The property is 500 yards from the city center and a 4-minute walk from Fort Zachary Taylor State Park Beach. The air-conditioned vacation home is composed of 1 separate bedroom, a living room, a fully equipped kitchen with an oven and fridge, and 1 bathroom. Towels and bed linen are available in the vacation home. For added privacy, the accommodation features a private entrance. Popular points of interest near the vacation home include Ernest Hemingway Home and Museum, Southernmost Point, and Duval Street. Key West International Airport is 2.5 miles from the property.

Security/Safety • Guest Services • Air Conditioner • Child Friendly • Fireplace/Heating • Laundry • Pet Friendly

MONTHY STAYS ONLY Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private townhome (one of only seven available for rent) in the Shipyard section of the Truman Annex with its gated entrance and 24 hour security. Our Bermuda-style cottage is steps away from sunning yourself on the beach, at the pool or enjoying the excitement of Duval Street with its many award winning restaurants, unique shops, creative art galleries, lively bars and bawdy night clubs. The famed Mallory Square and the water activities are also a short walk away. And value? How about free reserved and secure parking behind my cottage? High speed internet connection and cable TV in both bedrooms?.

We also offer themed getaways for your honeymoon; anniversary; birthday or a week of romance.
NOTE: I HAVE NICE OPENINGS IN THE SUMMER AND FALL. IT WOULD BE MY PLEASURE TO GIVE YOU A GIFT CERTIFICATE TO ONE OF KEY WEST'S BEST RESTAURANTS.
We know you will enjoy building memories in our home as well as Key West. On my living room walls are paintings I have purchased in Cuba from my humanitarian and education trips to the island. The colorful and yet relaxing paint hues on the wall are from my visits to Bermuda which is why I call my vacation home 'A Touch of Bermuda in Key West'.

The bedroom configuration is the best. The master bedroom suite is upstairs and separate from the downstairs bedroom and bathroom. Both parties have great privacy by not sharing a bathroom between two bedrooms.

You will want to be outside much of the time so relax on my front porch facing picturesque Southard St. and say hello to your neighbors. Or for privacy, the very large back deck with comfortable chairs for reading and a dining table for six to enjoy a private dinner under the stars.

Pets by special permission. No short weekend stays. It's not permitted by home owner association rules.

The Truman Annex is a former Naval base in the heart of Old Town in Key West. President Harry Truman used to vacation here so this residential complex is named after him. There is a wonderful tour available in the home he used as his summer residence. Duval Street is two blocks away. The pool is 100+ steps out my back garden gate down a pebble path. The best beach in Key West, Ft. Zachary Taylor State Park is within walking distance and if you have little ones, the Splash Pad at the end of the street is a joy. The famed sunsets at Mallory Square are short walk away as are the many tourist attractions such as Hemingway House; the Aquarium and Mel Fisher's Treasure Museum. And if water sports are your thing, the snorkel, scuba and fishing trips all start at the local pier within walking distance of my cottage.

Golf: There is an 18 hole golf course in Key West which is open to the public. It's not Pebble Beach or Augusta National but you can keep your game up to snuff by playing course the only one on the Keys. The links are within a short drive from my cottage but alas, this is one attraction not in walking distance. Good luck in breaking par.

Other Activities: Some really fine dining at award winning restaurants. On the walls of my living room, I have a painting of the Blue Heaven restaurant, one of my very favorites. It is quintessential Key West.

Come on down. Minimum stay is seven nights and all bookings are Saturday to Saturday except for special events such as boat race week and Fantasy Fest. Starting in 2026. I can only rent for a MINIMUM OF 28 NIGHTS (four weeks Saturday to Saturday)

PS If your party is small and you want another nice option for good value, check out my casita (condo) here in the Truman Annex # 1049465 on VRBO.
Keywords: Cottage; Townhome, vacation home

- "The location in the Truman Annex cannot be better. It’s a short walk to most attractions in Old Town. Jack provided excellent communication to ensure a smooth vacation. The property is as presented in the listing photos." - "We absolutely loved our time spent at Touch of Bermuda in Key West. Jack was great. Everything went so smoothly. We can’t wait to go back!" - "A great location, great host and great property! We loved it!" - "Update check in time!"

Cozy Key West Beach Cottage Walk to Beaches! is located in Key West, just 2 miles from Southernmost Point and 2.2 miles from Ernest Hemingway Home and Museum. The property is around 2.3 miles from Duval Street, 2.6 miles from Key West Aquarium, and 2.7 miles from Mallory Dock. Free Wifi is available throughout the property and Smathers Beach is 1.4 miles away. The air-conditioned vacation home is composed of 3 separate bedrooms, a fully equipped kitchen with a dishwasher and an oven, and 2 bathrooms. Towels and bed linen are featured in the vacation home. For added privacy, the accommodation features a private entrance. Mallory Square is 2.7 miles from the vacation home, while San Carlos Institute Casa Cuba is 2.4 miles away. Key West International Airport is 0.6 miles from the property.

Accessibility • Parking • Security/Safety • Laundry • Other • Guest Services • Internet • Child Friendly • View

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Pelican Suite is the ideal spot for your next getaway in Key West! This inviting suite is part of the Southernmost Sanctuary, providing easy access to shared hot tubs and a lovely outdoor patio perfect for soaking in the island ambiance. With a kitchenette, cable TV, and complimentary WiFi, you’ll feel right at home.

The Space:
Pelican Suite features a bright layout perfect for couples or friends, with two comfortable Queen beds for a restful stay. Just a short stroll away, you’ll find the lively attractions of historic Duval Street, where you can enjoy shopping, dining, and nightlife. Convenient amenities like a café, convenience store, gift shop, and bike and scooter rentals are all located on the same block. Don’t miss the iconic Southernmost Point, just one block away, and South Beach, only three blocks from your door. Pelican Suite is part of the Southernmost Sanctuary, a charming six-unit property that can be rented together for larger gatherings or family retreats.

Guest Perks:
Enjoy seamless, contactless check-in with our easy e-lock system. Pelican Suite is also pet-friendly, welcoming one small dog (30 lbs or less) during your stay. Please note that on-site parking is not available.

Neighborhood Highlights:
Pelican Suite is perfectly situated to explore the vibrant culture of Key West. You’ll have quick access to local cafés, bars, and unique shops, making it easy to embrace the island lifestyle.

Getting Around:
Key West is extremely walkable, but you can also rent bikes or scooters to explore the area. Rideshare options like Uber and Lyft are readily available for added convenience. If you need help with parking options, just let us know!

Other Things to Note:
-Shared washer and dryer available on-site.
-No parking on the property; street parking is an option.
-Pets are welcome! One pet (30 lbs maximum) with a $20 per night fee.
- Guests must be 25 years of age or older to reserve this property.

Check in time is 3:00PM
Check out time is 11:00AM

At Colocada Vacation rentals, we’re dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don’t hesitate to reach out! We’re here to help make your stay as special as possible.

- "Awesome little hideout! You feel like the only one on the island when you step in this quaint cottage! Great place to stay! " - "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Loved my time in this quiet little nook hidden among the best part of Key West."

Offering an outdoor pool, this historic Key West property is just 1 minutes’ walk from Duval Street. Free WiFi and a light continental breakfast are provided daily to all guests. All air-conditioned rooms include a cable TV and private bathroom. Cottages include a full kitchen and seating area. A pool view is included with select units at Courtney's Place Historic Cottages and Inns. Guests can grill a meal at the barbecue facilities. This Key West Courtney's Place Historic Cottages and Inns provides free on-site parking as well. The shops and restaurants of Mallory Square are 15 minutes’ walk away. Guests can also cool off at Smathers Beach 1.9 mi from the property.

- "We enjoyed our stay and would definitely stay there again." - "Had a great stay, hope to be back to stay again some day" - "Best stay we’ve had in Key West" - "Peaceful little gem in the centre of Key West" - "Perfect" - "Will be back" - "Great hospitality" - "We loved our visit and definitely will return." - "This is the only place we’ll stay here!" - "Great place - great staff - we can highly recommend this"

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Osprey Suite is the perfect choice for your next getaway in Key West! This charming suite is part of Southernmost Sanctuary, offering easy access to shared hot tubs and a delightful patio to soak up the island atmosphere. Equipped with a kitchenette, cable TV, and complimentary WiFi, you’ll feel right at home.

The Space:
Osprey Suite features a welcoming layout ideal for couples or friends, with a comfortable Queen bed and Queen sleeper sofa for flexibility. You’re just a short stroll from the lively attractions on historic Duval Street, where you can indulge in shopping, dining, and nightlife. Nearby, you’ll find a cafe, convenience store, gift shop, and bike and scooter rentals, all within the same block. Don’t miss the iconic Southernmost Point, just one block away, and South Beach, only three blocks from your door. Osprey Suite is also part of the Southernmost Sanctuary, a charming six-unit property that can be rented together for larger gatherings or family retreats.

Guest Perks:
Enjoy hassle-free, contactless check-in with our convenient e-lock system. Osprey Suite is pet-friendly, allowing one small dog (30 lbs or less) to join your stay. Please note that parking is not available on-site.

Neighborhood Highlights:
Osprey Suite is ideally located to explore the vibrant energy of Key West. You’ll have easy access to local cafes, bars, and unique shops, making it simple to immerse yourself in the island lifestyle.

Getting Around:
Key West is incredibly walkable, but you can also rent bikes or scooters to discover the area. Rideshare options like Uber and Lyft are readily available for your convenience. If you need assistance with parking options, just reach out to us for recommendations!

Other Things to Note:
- Shared washer and dryer are available on-site.
- There is no parking on the property. Street parking is available.
- Pets are welcome! One pet (30 lbs maximum) with a $20 per night fee.
- Guests must be 25 years of age or older to reserve this property.

Check in time is 3:00PM
Check out time is 11:00AM

At Colocada Vacation rentals, we’re dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don’t hesitate to reach out! We’re here to help make your stay as special as possible.

- "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This room with kitchenette was perfect. It was much bigger than I expected and close to lots of things to do but not on top of all the noise. Pretty courtyard area with 3 hot tubs. And the floor was CLEAN. I can't tell you how many times I've been sorry I took my shoes off in some places. This place was very clean. And the hosts were very attentive."

Just a 5-minute walk from Ernest Hemingway Home and Museum and half a mile from Southernmost Point, The Cozy Little Cottage features accommodations in Key West with a terrace. This apartment features private check-in and check-out and free Wifi. The property is 200 yards from the city center and a 8-minute walk from South Beach. The air-conditioned apartment is composed of 1 separate bedroom, a living room, a fully equipped kitchen, and 1 bathroom. A flat-screen TV is available. The accommodation is non-smoking. A bicycle rental service is available at the apartment. Popular points of interest near The Cozy Little Cottage include Fort Zachary Taylor State Park Beach, Higgs Beach, and Duval Street. Key West International Airport is 2.5 miles from the property.

- "So great that we would love to visit again!" - "We would definitely stay here again. Wonderful experience!" - "The Cozy Little Cottage was an exceptional choice for our Key West getaway!!" - "A awesome unexpected gem." - "This is THE place to stay in Key West!" - "If it wasn’t for the parking issue - GREAT!" - "Quick trip but wonderful stay!" - "Clean, modern, great location, quiet, would use this location again and recommend it to friends."

This charming one bedroom cottage is the perfect hideaway.

The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, and Hog's Breath as well as a plethora of delicious restaurants. Venture just a short distance further to Mallory Square or the famous Historic Seaport. It's easy to see why this location is unbeatable. The shared compound, of 6 total homes, features a winding brick pathway surrounded by tropical foliage and flowers that lead to a free form heated pool tucked away in the far side of the gardens. Take a refreshing dip, lounge and catch some sun, or enjoy a good book while being surrounded by beautiful trees and plants. This truly is a relaxing outdoor oasis!

This bright and airy cottage has tile floors throughout, a king sized bed, spa bath, a shared free form pool and washer/dryer. There is also a good-sized private deck with outdoor furniture for your enjoyment and comfort.

(The Ann Street Compound Homeowners Association requires all occupants to be 16 + yrs. Regretfully, NO Children under 16 are allowed. This home is also not pet-friendly)

STREET PARKING ONLY

Bedding: 1 king

- "My husband and I just returned to KW for a last minute trip for some fun and R&R. Check in was a breeze, close to airport and a great little find. Clean, spacious, well equipped and perfect walking distance to Duvall, Mallory Square and the marinas. We rented a golf cart from JV around the corner and had to park it at his lot when not in use because there is one (1) free space for the whole street. We were lucky enough to get it once. If you rented bikes, you could have easily parked them inside the fence. But golf carts park like cars and parking is expensive in KW. The parking and one other negative for us, that was part of our reason for leaving was the bed. For us it was very firm and uncomfortable, same with pillows. That said, beds aren’t universal so if a firm bed is good for you, definitely lock this place in. With the combo of beds and pillows I may have gotten 2-3 hours a night of sleep. So we decided to leave one day early, just exhausted from walking on average 5 miles a day and not sleeping well. Again- beds aren’t universally comfortable. The place had everything you need, well appointed and some goodies left from other travelers as well. Had one maintenance email I sent and the guy was there in literally 10 minutes. Great communicators and a great place. The pool was also nice, quiet little spot."

Well set in the center of Key West, Key Lime Cottage provides air-conditioned rooms, a garden and free WiFi. This property is located a short distance from attractions such as Mallory Square, Duval Street, and Ernest Hemingway Home and Museum. The inn has city views and an outdoor pool. At the inn, every room includes a patio. All guest rooms in Key Lime Cottage are equipped with a TV and free toiletries. Popular points of interest near the accommodation include Simonton Street Beach, Key West Aquarium and Mallory Dock. Key West International Airport is 2.5 miles away.

Child Friendly • Air Conditioner • Parking • Pet Friendly • Sports/Activities • Security/Safety • Pool • Internet • View

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!

THE PROPERTY: This home’s white picket fence and rocking chair front porch beckon you to come inside. Explore the uniqueness of this updated property including its location in Bahama Village, private pool, and pool house.

As you enter your vacation home, enjoy the open concept living room, kitchen, and dining area. In addition, there is a built-in work station for homework or working from home. The kitchen has plenty of storage, stainless steel appliances, granite countertops and a peninsula for entertaining. Through the kitchen you will find the relaxing primary bedroom. Here you may slumber in the queen bed, watch TV, or enjoy a delightful book in the reading chair. The main bathroom is updated and includes a shower/tub combination in pumpkin onyx tile as well as a single vanity with granite countertop. Built-in storage drawers are conveniently located just outside the main bath. Exit from the primary bedroom to the backyard pool area.

The cocktail pool is perfect for cooling off after a day on Duval Street. The outdoor shower will not only rinse you off after a swim but can serve as your pool house guest’s shower. The fenced backyard area is comfortably furnished with a dining set and umbrella for dining poolside. A gas grill is provided for the chef in your family. Natural light, air conditioning, ceiling fans and hardwood floors add to the comfort of this home away from home. Come immerse yourself in the charm of Key West from this 1923 ‘shotgun’ style home!

BED CONFIGURATION: There is a queen bed in the main house and a queen sleeper sofa in the pool house.

OUTDOOR AMENITIES: There is a cocktail pool with marble-like trim just off the covered back porch. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. The deck is furnished with a dining table, chairs, and umbrella as well as a gas grill and outdoor shower. Don’t forget to do a little people watching from your front porch!

PARKING: No designated parking spot. On-street parking available in the neighborhood.

LOCATION: Historic Old Town, in Bahama Village south of Truman Ave, between the Southernmost Point and the Hemingway House. The area features beautiful historic cottages and quiet tree lined streets. Walkable to several shops, restaurants, and the community pool.

PETS: This home is NOT pet-friendly. (If you have pets, please browse through our many homes that are pet-friendly.)

SMOKING: This is a non-smoking home and property.

***Guests must be 25 years of age or older unless accompanied by an adult***

***Please note that the cleaning fee includes a full "mid-stay" clean***

***Managed by Historic Key West Vacation Rentals***

- "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The management company is excellent, esp Susan. The cabana is just fine for guests' brief, 1-2 night, stay. It is also quite nice for separating to get laundry done quietly, or read a book or watch TV. The pool lights are lovely at night."

A 12-minute walk from Duval Street in Key West, Petronia Cottage provides accommodations with access to spa facilities. This vacation home features air-conditioned accommodations with a patio. The property is 0.6 miles from the city center and a 19-minute walk from South Beach. The vacation home features 2 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are available in the vacation home. The property has an outdoor dining area. Guests are welcome to eat at the on-site restaurant. For guests with children, Petronia Cottage offers a children's playground. Guests at the accommodation can enjoy cycling nearby, or make the most of the outdoor pool. Popular points of interest near Petronia Cottage include Ernest Hemingway Home and Museum, Southernmost Point, and Key West Aquarium. Key West International Airport is 1.9 miles from the property.

Fireplace/Heating • Wellness Facilities • Laundry • Security/Safety • Air Conditioner • Sports/Activities • Pool • View • Barbecue/Outdoor Cooking • Balcony/Terrace • Child Friendly • Guest Services

Description: Welcome to Corazon, a stunning 2-bedroom vacation rental in the heart of Key West's Old Town neighborhood. With its open floor plan, fully equipped kitchen, and private pool steps from the living area, this is the perfect home for entertaining and relaxation.

Located just one block from the famous Duval Street, Corazon is the ideal spot for experiencing all the excitement and culture that Key West offers. Plus, with the added convenience of the included parking space, you can easily run errands, grocery shop, or even take a day trip up the keys!

Inside, you'll find two spacious bedrooms - one on the second floor and another on the third floor - along with a second-floor study, perfect for those who need to stay connected while on vacation. And with an estimated 2160 square feet of space, Corazon is one of the largest 2-bedroom vacation rentals in Key West's Old Town district.

Linens, free high-speed Wi-Fi, and central air conditioning are all included, ensuring that your stay is as comfortable and convenient as possible.

Please note that due to city ordinance, Corazon is available for monthly rental only, with a minimum of 28 days required. Unfortunately, pets are not allowed.

Don't miss out on this chance to experience the beauty and excitement of Key West from the comfort of your private oasis at Corazon. Book your stay today!

Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know.

Parking: 1 Space

- "Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This is our 2nd year at this rental. Great location and the house has everything you could possibly need for your stay." - "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We've stayed at Corazon for 18 years in February. It's a great home made for vacation living, close to lot's of restaurants, shopping and things to do of all types!"

Scott's Cottage - Truman @ Duval Unit F offers accommodations in Key West, a 15-minute walk from Key West Aquarium and 0.9 miles from Mallory Dock. The property is close to several well-known attractions, a 17-minute walk from Mallory Square, 0.4 miles from San Carlos Institute Casa Cuba, and a 8-minute walk from Jackson Square. The property is a 7-minute walk from South Beach and within 300 yards of the city center. The air-conditioned apartment is composed of 1 separate bedroom, a fully equipped kitchen with an oven and a microwave, and 1 bathroom. Towels and bed linen are featured in the apartment. The accommodation is non-smoking. Popular points of interest near the apartment include Ernest Hemingway Home and Museum, Duval Street, and Southernmost Point. Key West International Airport is 2.5 miles away.

Child Friendly • Security/Safety

Welcome to the Jolly Rooster!

We’re thrilled to welcome you to our newly renovated, standalone cottage—proudly presented by the owners of the Dancing Rooster. Thoughtfully designed for relaxation and comfort, the Jolly Rooster comfortably hosts up to six guests and blends island charm with modern convenience.

Nestled just one block from vibrant Duval Street, you’ll be steps away from Key West’s best dining, shopping, and nightlife—while still enjoying the peace and privacy of your own retreat. Our cottage comes fully equipped with all the essentials for a carefree and memorable stay.

Come unwind, explore, and experience the best of island living at the Jolly Rooster!
________________________________________
The Space

This thoughtfully designed retreat includes:

• 2 private bedrooms, each with a queen bed + ensuite bath (walk-in showers)
• Spacious living area with American Leather queen sleeper (memory foam, no bars/springs)
• Smart TVs + high-speed internet throughout
• Private entrances for both bedrooms and living room
• Sleeps 6 (note: base rate covers 4 guests; $100/night applies for 5th/6th guests using sofa bed)
________________________________________
Fully Equipped Kitchen

Perfect for prepping anything from snacks to full meals, featuring:
• Granite countertops
• Cooktop stove and Range
• Microwave
• Refrigerator with ice maker
• Coffee maker, toaster, and blender
________________________________________
Location Highlights

• 1 block from Duval Street
• Walk to Hemingway House, Marina District, beaches
• Across from Sugar Apple natural food café
• 1 block to CVS + bike/scooter/golf cart rentals
• Duval Loop (free shuttle) stops ½ block away
________________________________________
Parking & Transportation

No dedicated parking. Free street parking on Simonton (first come, first served).
Explore by foot, bike, scooter, or golf cart!
________________________________________
Other Things to Note

3-night minimum stay
No smoking
We recommend travel insurance—especially during hurricane season (June 1–Nov 30). No refunds for weather or early departures.

Travel insurance is strongly recommended, especially during Florida’s hurricane season (June 1 – November 30). No refunds will be issued for weather-related disruptions or early departures. You may consider providers such as Travel Guard (AIG), Nationwide, Allianz, Berkshire Hathaway, or Red Sky.

Parking • Ocean View • Internet • Tv • Wellness Facilities • Kitchen • View • Balcony/Terrace • Air Conditioner • Laundry • Bedding/Linens • Security/Safety

Passover Cottage offers accommodations in Key West, a 17-minute walk from Key West Aquarium and 0.9 miles from Mallory Dock. Guests may go for a swim in the private pool. The property is 500 yards from the city center and a 14-minute walk from South Beach. The air-conditioned vacation home is composed of 2 separate bedrooms, a fully equipped kitchen with a dishwasher and an oven, and 2 bathrooms. Towels and bed linen are featured in the vacation home. The accommodation is non-smoking. Popular points of interest near the vacation home include Duval Street, Ernest Hemingway Home and Museum, and Southernmost Point. Key West International Airport is 1.9 miles away.

Child Friendly • Security/Safety • Pool

THE PROPERTY: Welcome to your private rocking chair front porch and tropical, Adult Only setting! As you enter your quaint cottage, you can sit back and relax in the comfortable living room with ample seating for you and your guests. The room is enhanced by a vaulted ceiling, coveted Dade County pine, and French doors that lead out to the lush gardens. A wet bar area is complete with a beverage refrigerator, a bar sink, microwave and a coffee maker. Beyond the family room is a convenient first-floor full bath with a walk-in shower. Just outside this bath is an open staircase that provides access to the upstairs open loft bedroom. This sleeping area has a window and is complete with a queen bed, chair, lamps, and dresser storage. Towards the rear of the home is the sunny first floor primary ensuite bedroom with king bed, storage closet and French doors. The ensuite bath has a beautiful walk-in shower, double sinks, and enclosed water closet. Please note this home has no washer/dryer at this time. Enjoy island life in Hibiscus Cottage- a convenient location with a shared pool!

BED CONFIGURATION: One king bed on the first floor and a queen bed in the upstairs open loft space.

OUTDOOR AMENITIES: A large shared pool is available for Hibiscus Cottage guests; it is located at the back of the complex and is surrounded by swaying palms and tropical landscaping. Loungers are in place for your use.

PARKING: No designated parking. Limited on-street parking may be available in the neighborhood.

LOCATION: Historic Old Town, walkable to Duval Street, shops, bars, and restaurants. Enjoy nearby entertainment on Mallory Square.

PETS: This home is NOT pet-friendly. (If you have pets, please browse through our many homes that are pet friendly).

SMOKING: This is a non-smoking home and property.

***Guests must be 25 years of age or older to rent; please note this is an18 and older complex.

***Hibiscus Cottage is independently managed by Historic Key West Vacation Rentals. At this time, it does not participate in the amenities and activities offered at the resort***

- "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a wonderful stay at the Hibiscus Cottage. It has obviously had a recent renovation but did not lose the look and feel of an old conch house. Comfortable furnishings and a surprisingly large master with an en-suite bath that would rival that of a five star hotel. We enjoyed coffee on the front porch swing and breakfast from Fausto’s on the private deck. The property itself is also so beautiful with lush tropical gardens surrounding your every move. To top it off, the location is unbeatable. One block off Duval and just a few blocks from Mallory Square and many of the great restaurants in Key West. We will not hesitate to rent this little gem again."

Charmayne's Cottages - Truman @ Duval is located in Key West, just a 15-minute walk from Key West Aquarium and 0.9 miles from Mallory Dock. This vacation home offers accommodations with a balcony. The property is 300 yards from the city center and a 7-minute walk from South Beach. The air-conditioned vacation home is composed of 7 separate bedrooms, 2 living rooms, a fully equipped kitchen with a dishwasher and oven, and 6 bathrooms. Towels and bed linen are offered in the vacation home. The accommodation is non-smoking. Popular points of interest near the vacation home include Ernest Hemingway Home and Museum, Duval Street, and Southernmost Point. Key West International Airport is 2.5 miles from the property.

Child Friendly • Security/Safety

Turtle House. A Key West Artist's oasis. Now available for March 2023. Easter in Key West!

Delight in the uniqueness of this property. It is a compound comprised of two former cigar maker’s cottages, redesigned and renovated by the artist and her late husband, an architect. Turtle House has been featured in several magazines, including the April 2009 edition of Coastal Living Magazine, and Design Within Reach summer catalogue 2019. Turtle House is located on a quiet lane in Old Town Key West near the cemetery.
Come finish your novel or dip your body into the sunken black tiled jacuzzi. Dine under the covered breezeway underneath a bamboo pergola, protected from weather, with beautiful views of the garden illuminated at night by solar lighting. You will find magic and inspiration at Turtle House, along with all the comforts and amenities of modern living including a parking space that is part of the property.
For those who seek elegant simplicity and a refuge in nature, this may be your dream come true! With privacy difficult to find in Key West... bike or walk to your favorite restaurant or cook at home on the gas grill and eat under the stars! Wake up to the song of birds and sleep peacefully to the sound of tree frogs and crickets.
The house is appointed with beautiful linens, dishes and cookware that offer a comfortable elegance to the rustic design of the cottages, The principle bedroom is its own cottage, furnished with a king size bed, an excellent mattress, two small sofas and a TV for streaming your favorite films. There is a full indoor/outdoor bath attached to the cottage that can be accessed from the cottage or from the deck. The second (guest) bedroom is located in the main cottage. It is a charming salon , designed as a guest room with a twin bed (brand new mattress) and its own bathroom which opens to both the guest room and the living room. This little bedroom faces the lane with a beautiful garden just ouside the window. It is a wonderful place for an afternoon nap!

Turtle House is perfect for a couple, and or a single person who wants to enjoy all that Key West offers, and yet values a return to a peaceful haven. A perfect spot for a poet, or a poetic soul, a writer, an avid reader, an architect, a lover of architecture! Or simply someone who loves the simple pleasures of life amplified in this domain. The lush gardens have been lovingly cultivated by the artist, herself. The owner does not pack away her personal dishes or towels or favorite linen pillows and throws. She hopes you will find inspiration and respite in this unique hide away, as she does.

Come and enjoy TURTLE HOUSE.

Turtle House has become available from November 21st thru February 10th with a 30 day minimum stay. Ideally it would be wonderful to rent to one person or couple for the entire stretch, but I am open to discussing....

It is truly a little jewel. (Not for partiers, smokers, heavy drinkers, revelers.)

- "The home and environment of this accomplished painter is full of Old Key West charm. It was easy to hop on our bikes and explore Old Town, the beaches, the harbor (though I was perfectly happy hiding out in the garden!!!!) The abundant gardens, the unique open-air architecture, the lovely linens and towels and well-stocked kitchen made our stay comfortable and romantic. Turtle House is indeed an oasis of serenity, beauty, and creativity. "

Charming Pool Cottage in the Heart of Old Town Key West

Perfectly situated in historic Old Town Key West, this quaint and inviting pool cottage offers the ideal island escape for a couple, with room for occasional guests. Thoughtfully decorated and impeccably maintained, the home features a newly renovated kitchen and beautifully designed outdoor spaces to enjoy the island breeze.

Property Highlights:
Comfortable Accommodations:
The primary bedroom includes a cozy queen bed, while the guest bedroom offers two single beds—perfect for visiting friends or family.

Modern Conveniences:
A full-sized, fully equipped kitchen opens directly onto the stunning pool deck—ideal for entertaining. A stackable washer and dryer are included for added convenience.

Outdoor Living at Its Best:
Private Pool: Cool off or unwind by the pool, which can be heated for year-round enjoyment.
Front Porch: Sip your morning coffee and watch the world go by from the charming front porch.
Back Deck: Host a barbecue or relax after a day exploring Key West in this serene outdoor space.

Parking:
Street parking is typically available within a block of the home.

Whether you're here for a weekend getaway or an extended stay, this delightful cottage blends classic Key West charm with modern comforts—making it your perfect home away from home.

STAYS FROM DECEMBER THROUGH APRIL NEED TO BEGIN ON THE 1ST OF THE CALENDAR MONTH - THANKS FOR UNDERSTANDING.

- "Great little house. Walking distance to pretty much all of old town area. Has a nice pool to relax in. HUGE bathroom. Bedrooms are nice sized. Washer/dryer is a huge plus for long stays. The only thing - wish it was closer to the beach…" - "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Lovely little house with a very nice pool, great location and great neighbours. A bike ride away to everything and a walk to restaurants and grocery shopping. It is ideal for 2 people and would be tight for 4 adults as the second bedroom is not very big and there is only one bathroom but it is a gigantic one! We will definitely be back. As per usual the management company was excellent and very responsive."

Quiet cottage in a located in new town. Quick taxi ride or bus ride to downtown. Do your Duval Crawl & then head back to a quiet peaceful and relaxing swim in the pool. Located on a private property with homeowners on site. Off-street parking and a private entrance to the cottage. No smoking & no pets. 2 people max. This is a minimum 28 day rental.

- "The place was perfect! The owner is a really nice lady and made sure i had everything i needed. The place is very clean bith inside and out and in a perfect location. Quiet but not too far from everything. I look forward tonstaying here again next year!" - "Friendly courteous communicative host. Clean comfortable location away from the noise and hustle of Duvall but easy bike to Duvall. The bed was very nice!" - "Everything better than expected. Eva the owner/landlord is on site. A couple minor issues with the internet, quickly resolved. Wonderful place, quiet and removed from the crazy downtown, but easy to get anywhere with a bike, walking or a ride service. "

THE PROPERTY: Enjoy your stay with us at Robinson Crusoe Cottage, part of the quaint Conch Cottages property, which includes 3 separate rentable units: Robinson Crusoe Cottage at the rear, Royal Poinciana Cottage on the right, and Margarita Cottage on the left. You can rent each unit separately or rent Conch Cottages to enjoy all 3 units and ultimate privacy during your Key West vacation.

A brick walkway paves the route through the front gate and to your private rear entrance. Here you will find lovely palm trees and lush landscaping. A shared, seasonally heated pool is also located in the rear of the property and is adorned with decking and loungers. Surrounded in sunshine, the pool is the perfect place for relaxing while working on your tan. Enjoy cocktails poolside or outdoor dining. A grill is provided for the chef in your group. No chef, no worries. You can walk or bike to nearby El Siboney, a well-known Cuban restaurant. Inside the cottage is an updated kitchen with refrigerator, microwave, toaster, and coffee maker. Preparing meals or a quick snack is easy in this well-equipped kitchen. *Please note this cottage has no dishwasher. The large living area is complete with a TV, pull-out sleeper sofa, end tables, and a dining table. Your queen bedroom is adorned with nightstands, bedside lighting, a TV, and closet. Its updated bath includes a large single vanity and sink and a tiled, walk in shower. Great for entertaining friends or keeping an eye on the kids, this open concept cottage has everything you need to enjoy a blissful stay.

BED CONFIGURATION: There is one queen bed in the bedroom and a sleeper sofa in the main living area.

OUTDOOR AMENITIES: A shared, seasonally heated pool and lounge chairs are provided for your enjoyment. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. The pool house has a shared washer and dryer for guests. A grill and dining table are provided for outdoor meals in the sunshine.

PARKING: There is no designated parking space however, street parking may be available in the surrounding neighborhood.

LOCATION: Located in the heart of Historic Old Town, you can walk or bike to Duval Street, shops, bars, and restaurants. Enjoy nearby entertainment on Mallory Square.

PETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.

SMOKING: This is a non-smoking home and property.

***Guests must be 25 years of age or older unless accompanied by an adult.

***Managed by Historic Key West Vacation Rentals***

Internet • Balcony/Terrace • Bedding/Linens • Tv • Wellness Facilities • View • Air Conditioner • Laundry • Guest Services • Ocean View • Barbecue/Outdoor Cooking • Security/Safety

Tucked away on a quiet street in the heart of Old Town Key West you will find the quaint and comfortable Ivy Cottage. This well-appointed home offers everything you will need to feel at home for your extended stay - a comfortable queen bedroom, fully stocked kitchen and living area, fast Wifi, private front and back porches, and a heated swimming pool. Here you are a quick stroll to the beach and lots of great dining, shopping, and attractions. One convenient parking space is included.

The "shotgun style" cottage opens to the queen bedroom, which leads to a hallway with storage, laundry, and the bathroom. The living area, kitchen, and dining space are in the back of the home, which opens to a porch with seating and dining for four. The swimming pool is just steps from the back porch, shared with the three other cottages on-site.

Wellness Facilities • Air Conditioner • Barbecue/Outdoor Cooking • Kitchen • Entertainment • Security/Safety • Laundry • Sports/Activities • Pet Friendly • Internet • Bedding/Linens • Balcony/Terrace

Cute Studio cottage with additional sleeping loft. Nicely landscaped shared pool and outside area. Walking distance to restaurants, docks, and Duvall St. Easy to get to everything yet quiet and secluded.

- "If you’re looking for seclusion and walkable, off the beaten path restaurants or busy boardwalk tourism, this cottage is perfect. So enjoyed our stay! And will return."

Summary:
Add this listing to your wishlist by clicking the ♥ in the upper right hand corner. This 1 bedroom/1.5 bathroom Key West cottage is the perfect place to relax and enjoy island living. With only 4 blocks to Duval, walking to dinner or to famous sites is easy. Central to Mallory Square and the Southernmost Pointe means that you have your pick of places to choose from. Enjoy the front and back porches as you cool off in the shade. Stylish, clean, and private, you don't want to pass on this retreat.

The Space:
Relax and create long-lasting memories in this beautifully well-appointed home! The Havana Cabana offers a spacious interior, an open and fully equipped kitchen, living, and dining area, free WiFi, and two porches. This two-story house is the perfect place to enjoy Key West to the fullest!

What’s nearby:
This property is centrally located in Old Town Key West. It is a quick walk or Uber ride to all of what Key West has to offer.

Things to LOVE:

★ One bedroom/ one and half baths

★ Murphy bed for additional guests

★ Modern kitchen and bathrooms

★ Front and back porches

★ Smart TVs and smart locks

★ Washer + dryer

★ Driveway parking for 1 car

★ Short walk/drive to shopping and dining

★ Keurig, iron, and hair dryer

★ High speed WIFI

Guest Access:
The home is equipped with a remote lock. The guests will have a code during their stay where they can access with a self checkin.

The Neighborhood:
This delightful duplex is located in a part of town called The Meadows. This exclusive residential area of Old Town Key West is really an extension of the Old Town Historic Seaport District where the harbor 'rounds the bend.' It was originally developed as a suburban neighborhood in the early 1900's and has a distinctively gracious and private feel with wider tree lined streets and larger yards. There is less commercial development than the seaport side of White Street and the center of Old Town. Yet, the Meadows is flanked by White Street that offers many locally favorite restaurants, art galleries, bakeries, and shops.

Getting Around:
Guests can travel throughout Key West on foot, bike, golf cart, Uber, or your personal vehicle. There is one off street parking space for the house.

Other Things to Note:
28- night minimum stay.

Please note there are two rental units within this house. It is important that guests are respectful of quiet hours between 10 p.m. and 7 a.m.

If you are interested in renting both sides of the unit please contact the Host and I will direct you to the joint listing.

Due to the open stair case, this home isn't recommended for people who are traveling with young children.

- "The owner Corey is a Jem to work with !! Walking up to the house, it's well maintained and looks like a postcard of a Key West house. There's a front porch with a seating area and an OFF-ROAD PARKING SPOT (driveway). Open the door and WOW, the place is clean and modern. It's layout is FANTASTIC. Everything is new and fresh, there's a table with 4 chairs, a TV area with a comfortable love seat with a comfortable queen murphy bed like I've never seen before, a nice kitchen area with modern appliances, a dishwasher is an unexpected bonus and a super clean full bathroom with a walk-in shower. Upstairs is a comfortable queen bed with a BONUS half bath which is great in the middle of the night. Out the back door is a nice sized porch that gets a lot of sun in the early afternoon with 2 loungers and 2 chairs. Now the location is just perfect - it's 2 blocks from Duval which means that it's quiet and peaceful. You're just a block and a half from the Duval Loop (free bus) so, you can get to the other side of Old Town without a Taxi or walking. Overall - this is the nicest place that I've ever stayed in Key West, I've been visiting for 20 years. and I'd recommend it to you."

The newly remodeled home is located in the middle of Old Town down a private lane just a block from Duval Street. One off-street parking space is provided, not that you really need a car. You are less than a mile from the Old Town attractions but there are bikes available for your use if you want to venture further out. When you enter the front gate you walk onto the front deck where you can grill out and enjoy dinner under the stars and palm leaves or just relax in the hot tub. There is also a rear deck off of the home with couple of chaise lounges chairs great for sunbathing. Along the side of the home is an outside shower that is great to use when you return from the beach or really anytime. When you walk into the home via the large sliding patio door you enter the living room and dining area. In the living room there is a large couch (queen size sleeper sofa) with chaise lounge and 55" Smart TV. Dining area features a 4 person table and bar top with seating for 3. The kitchen features Cafe appliances, smooth top range, microwave, dishwasher, refrigerator, quartz countertops and Kohler coffee maker. The main bathroom has 36" floating vanity with a lighted Kohler medicine cabinet mirror and tile shower with shower head, couple of body jets, and handheld shower wand. The bedroom has a king size bed with nightstands on each side, a 44" Smart TV mounted on shiplap wall and a patio door that leads to rear deck. The half bath off of the bedroom also includes the LG laundry center and built in closet storage center. Enjoy all that Old Town Key West has to offer just steps from your home or don't go anywhere and just enjoy relaxing at home.

- "Everything was super easy from the check in to check out. The location is a block from all the action on Duval but absolutely no noise when at home. Parking & the bicycles were a huge plus. All the appliances and interior are ultra modern. We will be back. Ed K"

Located in Key West, this welcoming cottage lets you experience it all. Key West Cemetery and The Kite House are just a short walk away.

After you return, you can unwind by the outdoor pool or sip a drink on the patio; you may also like the BBQ grill. For a change of scenery, come inside and enjoy the free WiFi and TV.

As you settle into this 2-bedroom, 1.5-bathroom rental, you'll find a living room, air conditioning, and a ceiling fan. Prepare a home-cooked meal in the kitchen, complete with an oven, a stovetop, and a refrigerator, as well as cookware. And you won't have to pack extra clothes, because you'll also have a washer/dryer.

Internet • Kitchen • Tv • Air Conditioner • Laundry • Pool

Located in Key West, this welcoming cottage brings it all within your reach. USCGC Ingham Maritime Museum and Jackson Square are just a short walk away, so leave your car at the property, which offers onsite parking.

Spend a day at the nearby beach, relax by the outdoor pool, or sip a drink on the patio of this cottage. When you come inside, connect to the free WiFi or get cozy in front of the digital TV (streaming services available).

As you settle into this 2-bedroom, 1-bathroom rental, you'll find air conditioning, a ceiling fan, concierge services, and tour/ticket assistance. Bathroom amenities include free toiletries, towels, and toilet paper. The kitchen is equipped with an oven, a stovetop, and a refrigerator, as well as a coffee maker and cookware. And you won't have to pack extra clothes, because you'll also have a washer/dryer.

Laundry • Pool • Kitchen • Bedding/Linens • Air Conditioner • Internet

Caroline's Cottage KW is full of amenities for all your needs. The real feel of the home away from home. Smart TV's, Washer Dryer, Full size kitchen, and a variety of appliances. Remote work on 1000mbps Fiber Optic Internet is not a problem in this very friendly relaxed neighborhood . There is even two complimentary bikes for guest to use if you want to get a closer feel of the island breeze and day to day life in Key West.

The space
Nice porch to have your morning coffee on while the island sun rises over the clouds. There's even a smaller porch on the backside of the cottage where the laundry machines are located.

Guest access
Guest can use the whole cottage, but hosting of parties or any events are prohibited.

Other things to note
No Children allowed under 13 on premises. Children 13-17 are allowed on premises with adult supervision by parent at all times. Maximum night stay at cottage is 31 nights.The $1500 deposit must be paid prior to stay to complete the booking process for the cottage. Without the deposit being paid the booking can not be accepted and will need to be canceled.

Hangers • Room-darkening shades • Hair dryer • Dryer • Bed linens • Hot water • Essentials • Cleaning products • Shower gel • Washer

"La Casita"- Completely remodeled and Fully Furnished Old Town Key West cottage 10 min Walking distance from the White street Pier. Perfect for relaxing or guests who want enjoy Key West and work remotely. Cottage offers everything you'll need for the perfect getaway. TV,s, Internet, desk, Washer and Dryer, SS Appliances ,Hot Water , Memory Foam mattress ,outdoor grill and Nespresso coffee maker.28 days minimum stay!

Central air conditioning • Hangers • Shampoo • Free washer – In unit • Free dryer – In unit • Iron • Central heating • Essentials • Hair dryer • TV

Former residence of an author and decorated accordingly, this cute cottage is quintessential Key West. Perfectly maintained monthly rental has two bedrooms, one full bath plus outdoor shower, is an authentic Old Town Cigar Maker's Cottage and the location of the actual writing of Laurence Shames' famous book FLORIDA STRAITS. Key West is a former home of many other authors including Ernest Hemingway and this lovely getaway reflects that heritage in its decor and lending library!

The space
Super close to the fishing pier, restaurants, a grocery store at the end of the block. 10 minute walk to Duval.

Guest access
Pool and spa/hot tub on premises. Recently renovated hot tub and deck area. Private deck with outdoor shower and grill

Other things to note
Lush foliage and brick meandering walkways surround the swimming and wading pools. Brand new living room furniture and decor in 2019. All new memory foam mattresses. Brand new shower head with features, brand new sink faucet, new ceiling fans as of 1/21, newly finished bar area, brand new hot water heater. Cable and access to your smart network on roku, blue ray player as well. Other features of this charming home include hardwood and tile floors, ceiling fans and central a/c in every room, a large eat in kitchen with all appliances and kitchen items/utensils including dishwasher, high ceilings, sun room, and an expansive deck with gas grill perfect for entertaining. In home washer and dryer, cable TV, WIFI, DVD and movies.

Hot water • Essentials • Iron • Washer • TV • Dryer • Hangers • Heating • Air conditioning • Hair dryer

This two-bedroom Key West Writer's Cottage is a serene haven for creative minds and vacationers. It features a cozy living area with charming decor that inspires relaxation. Enjoy the relaxing deck for morning coffee or unwinding with a book, and take a refreshing dip in the inviting pool. Each comfortably furnished bedroom ensures a restful night’s sleep, and the fully equipped kitchen is perfect for cooking. Plus, you can easily bike to the nearby boardwalk and beach for fun in the sun!

The space
Experience the charm of this Key West Cottage with two uniquely themed Hemingway bedrooms. The first bedroom, "The Old Man's Retreat," captures the spirit of deep-sea fishing adventures with nautical décor, vintage fishing gear, and warm, earthy tones that evoke the tranquility of the ocean. The second bedroom, "Carribean Escape," transports you to the literary cafés of Paris, featuring classic Hemingway quotes, elegant French artwork, and a cozy reading nook that invites you to unwind with a good book and a glass of wine.

Guest access
Welcome to your Key West Cottage getaway! As our guest, you’ll have exclusive access to both beautifully themed bedrooms, a fully equipped kitchen for your culinary adventures, a cozy living area to relax in, and a bathroom stocked with essentials. Don’t forget to unwind in the sun lounging chairs by the pool, where you can soak up the Florida sunshine and enjoy the tranquil surroundings. Your perfect retreat awaits!

Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location.

The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, and Hog's Breath as well as a plethora of delicious restaurants. Venture just a short distance further to Mallory Square or the famous Historic Seaport. It's easy to

The space
Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location.

The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, and Hog's Breath as well as a plethora of delicious restaurants. Venture just a short distance further to Mallory Square or the famous Historic Seaport. It's easy to see why this location is unbeatable. The shared compound, of 6 total homes, features a winding brick pathway surrounded by tropical foliage and flowers that lead to a free form heated pool tucked away in the far side of the gardens. Adjacent to the pool area is a shared, coin-operated laundry facility. Take a refreshing dip, lounge and catch some sun, or enjoy a good book while being surrounded by beautiful trees and plants. This truly is a relaxing outdoor oasis!

The Old Town Bali Hideaway studio has a queen-size bed and sitting area, efficient European-style kitchen, bath with walk-in shower, tiled floors and Bamboo ceilings. Relax in the private fenced-in patio courtyard or around the large, shared free-form pool and tropical garden. Here at Bali Hideaway you will feel as though you are in a peaceful retreat, yet still a part of all the Key West action. A perfect alternative to the high priced hotels in the adjoining area.

(The Ann Street Compound Homeowners Association requires all occupants to be 16 + yrs. Regretfully, NO Children under 16 are allowed. This home is also not pet-friendly)

STREET PARKING ONLY

Bedding: 1 queen

Guest access
Key entry. Code for compound gate will be given at check-in.

Other things to note
Rent Key West Vacations is happy to represent this property and 60 others offered here. All availability calendars are tied to our reservation system, so they are always current. We are happy to answer any questions you may have.

Essentials • AC - split type ductless system • Paid dryer – In building • Hangers • TV • Iron • Smoke alarm • Bed linens • Paid washer – In building • Hot water

Colony Calypso - is a charming one bedroom bungalow located in Historic Old Town Key West. This one level cottage has an open living/dining area, full kitchen and spacious bedroom with king size bed. Located on a compound with a large shared pool.

The space
Part of a small collection of cottages known as The Colony, this quaint cottage sits to the back of the property and is located just two blocks from world famous Duval Street. Colony Calypso is surrounded by coconut palms and blooming bougainvillea. This charming one bedroom bungalow is a true island hideaway.

The cottage features a one level open concept living and dining area with a full kitchen. The quaint cottage offers a spacious bedroom with a king size bed. The bathroom has a tiled shower bathtub combination.

The cottage offers a nice private deck with a gas grill. The tropical common area grounds feature a large, beautiful swimming pool. Colony Calypso's convenient location and a quiet atmosphere make this a perfect place to relax in the comfort of your home away from home while still being in Old Town and close to Duval Street.

This vacation rental property offers secure, coded keyless entry with contactless check in.

Bedding: 1 king, 1 sleeper sofa

Parking: There is a small parking lot for cottage guests and available on a first come first parked basis. If the lot is full, there is on-street parking right on Olivia Street and on surrounding side streets and lanes.

Guest access
Code for keyless entry give at check-in

Other things to note
Rent Key West Vacations is happy to represent this property and 60 others offered here. All availability calendars are tied to our reservation system, so they are always current. We are happy to answer any questions you may have.

Welcome to Osprey—a beautiful studio in the heart of Old Town Key West! Perfectly located at the Colony on Olivia Street, just two blocks from famous Duval Street, this ground-floor studio suite is equipped to make your stay in the islands comfortable and convenient. Osprey is both removed from and integrated into Old Town Key West. It is tucked away in a quiet neighborhood, but close enough to walk to any bar, restaurant, shop, or gallery. This is a non-smoking unit designed to accommodate two

The space
This charming suite is comfortably furnished with a queen bed, comfortable couch, flat-screen TV, and tropical artwork. An open floor plan creates a breezy atmosphere and the kitchenette features a coffee maker, microwave oven, stovetop, refrigerator, and the accessories to allow for small meal preparation if you aren't up for going out. A spacious bathroom with standing shower and full-length mirror completes this wonderful accommodation. The french doors lead out to an inviting deck close to the shared pool.

Other things to note
The Colony is a 10 unit compound just 3 blocks from Duval Street. There is a shared pool and coin laundry located within the complex. There are four off street parking spaces that are shared on a first come, first served basis. Anyone else must utliize street parking in spacing NOT marked "residential parking"

Wifi • Hot water • Refrigerator • Fire extinguisher • Air conditioning • Smoke alarm • TV with standard cable • Hangers • Bed linens • Iron

Ann Street Tranquility is a charming one bedroom one bathroom cottage in a tropical compound with a shared pool. Located steps off Duval next to The Curry Mansion. King sized bed, spa bath and private deck will make this a pleasant Key West vacation.

The space
This charming one bedroom cottage is the perfect hideaway.

The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, and Hog's Breath as well as a plethora of delicious restaurants. Venture just a short distance further to Mallory Square or the famous Historic Seaport. It's easy to see why this location is unbeatable. The shared compound, of 6 total homes, features a winding brick pathway surrounded by tropical foliage and flowers that lead to a free form heated pool tucked away in the far side of the gardens. Take a refreshing dip, lounge and catch some sun, or enjoy a good book while being surrounded by beautiful trees and plants. This truly is a relaxing outdoor oasis!

This bright and airy cottage has tile floors throughout, a king sized bed, spa bath, a shared free form pool and washer/dryer. There is also a good-sized private deck with outdoor furniture for your enjoyment and comfort.

(The Ann Street Compound Homeowners Association requires all occupants to be 16 + yrs. Regretfully, NO Children under 16 are allowed. This home is also not pet-friendly)

STREET PARKING ONLY

Bedding: 1 king

Guest access
Code for compound gate and door entry will be given ant check-in

Other things to note
Rent Key West Vacations is happy to represent this property and 60 others offered here. All availability calendars are tied to our reservation system, so they are always current. We are happy to answer any questions you may have.

TV • Iron • Hangers • Free washer – In unit • Fire extinguisher • Hot water • AC - split type ductless system • Bed linens • Free dryer – In unit • Smoke alarm

The newly remodeled home is located in the middle of Old Town down a private lane just a block from Duval Street. One off-street parking space is provided, not that you really need a car. You are less than a mile from the Old Town attractions but there are bikes available for your use if you want to venture further out. The home offers all the modern conveniences to make your stay pleasant and comfortable.

The space
When you enter the front gate you walk onto the front deck where you can grill out and enjoy dinner under the stars and palm leaves or just relax in the hot tub. There is also a rear deck off of the home with couple of chaise lounges chairs great for sunbathing. Along the side of the home is an outside shower that is great to use when you return from the beach or really anytime. When you walk into the home via the large sliding patio door you enter the living room and dining area. In the living room there is a large couch (queen size sleeper sofa) with chaise lounge and 55" Smart TV. Dining area features a 4 person table and bar top with seating for 3. The kitchen features Cafe appliances, smooth top range, microwave, dishwasher, refrigerator, quartz countertops and Kohler coffee maker. The main bathroom has 36" floating vanity with a lighted Kohler medicine cabinet mirror and tile shower with shower head, couple of body jets, and handheld shower wand. The bedroom has a king size bed with nightstands on each side, a 44" Smart TV mounted on shiplap wall and a patio door that leads to rear deck. The half bath off of the bedroom also includes the LG laundry center and built in closet storage center. Enjoy all that Old Town Key West has to offer just steps from your home or don't go anywhere and just enjoy relaxing at home.

Iron • Hot water • Hangers • Bed linens • Outdoor shower • Extra pillows and blankets • Washer • Dryer • Hair dryer • Cleaning products

This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the comfortable living room has a spiral staircase to the loft second bedroom with unique glass railing. Large windows in the kitchen bi-fold away to allow serving directly to the pool

The space
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the comfortable living room there is a spiral staircase to the loft second bedroom with unique glass railing. Large windows in the kitchen bi-fold away to allow serving directly to the pool deck and capture the warm, tropical, Key West breezes. If cooking isn't for you on your vacation, stop by the Banana Cafe Restaurant or one of the many other delicious options steps away on Duval Street. The Twins allow for great flexibility in your vacation planning. Rent this property as a two bedroom/one bath or add the other unit to make it four bedrooms/ two bath.
Bedding: 2 queens

Guest access
Keyless entry

Other things to note
Rent Key West Vacations is happy to represent this property and 60 others offered here. All availability calendars are tied to our reservation system, so they are always current. We are happy to answer any questions you may have.

Kick back and relax in this calm, stylish space, inside and outside living, full of sunshine!!!

The space
Amazing open water view, relaxing island living just fifteen minutes from downtown Key West. Enjoy quiet mornings and breathtaking sunsets.

Completely remodeled oceanfront home features 2 bedrooms, 2 bathrooms, beautiful new fully equipped kitchen, living and dining room and great outdoor space.

The master bedroom has a king size bed and private bathroom. The guest bedroom is furnished with a queen size bed and the guest bathroom can be accessed from the main living area. The living room and the master bedroom include smart TVs. As you exit the living room you can enjoy spectacular views from the upstairs patio overlooking the ocean.

Downstairs you can find a dining table, a seating area where to relax and enjoy a drink after your dinner, a grill and a refrigerator.

Enjoy a day in the sun with your family on the 4 lounge chairs you can find by the water or watch the most amazing sunsets from our tiki hut.

There is plenty of parking and storage available under the house.

The home is located within walking distance to several neighborhood attractions like tennis courts, basketball court, playground, picnic are, public boat ramp, sandwich shop and the famous Baby's Coffee.

Guest access
You can walk around or just bike to Babby's Coffee in the morning, or play some tennis or volleyball on the neighborhood courts.
Plenty parking underneath the house.

Other things to note
Amazing outdoor space

Hair dryer • Hot water • Cleaning products • Fancy conditioner • Bay view • Shower gel • Free washer – In unit • Fancy body soap • Ocean view • Shampoo

Featured on HGTV, Eleanor's Place Key West is a charming cottage located in historic Old town Key West, walking distance to Duval, beaches, restaurants, attractions and an olympic size pool.

SEARCH "Eleanor's Place Key West Cottage Rental" ON YOUTUBE FOR A VIRTUAL TOUR!!!

Queen and King Bedrooms
Open concept living and dining rooms
Chef's kitchen
Two full bathrooms
Lush private patio with bbq and overhead lighting.
Private parking
Dog-friendly - Some restrictions apply
28 night minimum stay

The space
THE PROPERTY: "Eleanor's Place Key West" has everything you might want on your monthly vacation to Key West.

SEARCH "Eleanor's Place Key West Cottage Rental" ON YOUTUBE FOR A VIRTUAL TOUR!!!

FEATURED on HGTV's Island Life! The living and dining is open concept and has ample natural light.

BED CONFIGURATION: Queen Bed on main floor with wall mounted TV - and King Bed in upstairs loft with ensuite bath. (Spare blowup mattress also available.)

LIVING SPACE: The living and dining room are open concept with large windows and ample light. The living room has a new sectional sofa, and the dining room has a table for four. The wall mounted TV can be angled to face either the living room or the dining room.

KITCHEN: The kitchen is spacious, includes a breakfast bar, stainless steel appliances including a dishwasher and convenient full size laundry machines.

BATHROOMS: There are two full bathrooms. One is located on the main floor and the other is an upstairs ensuite in the King loft bedroom.

OUTDOOR SPACE: The house features a beautifully lush side yard with an inviting patio, made from reclaimed bricks. Enjoy comfortable patio seating, barbecue, and overhead lighting under the stars.

PARKING: Side driveway and street parking.

LOCATION: The cottage is in historic Old Town Key West, just steps to Duval, beaches, restaurants, attractions, and an olympic size pool!


PETS: This home is dog-friendly. Some restrictions apply.

NOTES:
***Due to Key West Bylaws, a minimum stay of 28 nights is required. Guests check in on the 1st of each month. To book more than one month in a row and enjoy discounted pricing, please contact us.***

REVIEWS: Many people that stay at our cottage are repeat guests, and as a result there are not many reviews on this site. Below you will find some reviews from people who've booked privately (they have been cut and pasted from our website and not modified):

"We just got home from a one month stay at Eleanor’s Place (June 2025) and I can’t say enough about the cottage or our Host, Lesley. The cottage on Virginia Street is in a quiet friendly neighborhood, and the cottage itself, which is beautifully decorated, provided us with all the comforts of home, including a quaint backyard where we mingled with friends as we grilled on the BBQ. We were close to all the attractions and restaurants as well as the beaches, and Lesley was always quick to respond to any questions we had along with suggestions for our stay. To get around we rented a golf cart from Fun Rentals, which we were able to park in the driveway of the cottage. This was our fourth trip to Key West, and we wanted to live and play like a “local” and Eleanor’s Place helped us do that easily. If you are looking for a comfortable, relaxing, quiet place to stay in Key West…we highly recommend Eleanor’s Place." - Michelle, 2025
​
"If I could add more stars I would! I have been going to Key West every year, at least once a year, for close to 15 years. I have stayed in hotels, condos and houses and this is by far the best stay yet! House is spotless, bathrooms are immaculate, fantastic front porch for morning coffee and the patio is an absolute gem. All appliances are clean and work, location couldn’t be better! Walking distance to everything but far enough away from the chaos that your evenings are nice and quiet. Hosts were extremely responsive to any questions. I will say this now…if Eleanor’s Place is available…BOOK IT!" - Paul G., 2025

"Eleanors Place is a thoughtfully renovated shotgun house in the historic Bahama Village section of Key West. Having lived in Key West 22 years, you get the authentic island vibe here. Everything we needed was available and the full size appliances were a big plus. We enjoyed the tropical shaded side yard for dining, reading, and relaxing, and watching our pets play. The off-street parking and friendly neighbors are a bonus. You are only a few blocks to many of the best attractions: Southernmost Point, Hemingway home, lighthouse, Butterfly Conservatory and many good restaurants. We never walked over 1.5 miles to the furthest locations in Old Town, but if we needed transportation it was readily available. The public pool is a block away and they open early in the morning to swim laps. Lesley is a wonderfully responsive host which was much appreciated. Our month stay was delightful." - Delores, 2025


"We stayed at this cottage from mid June through all of July. We absolutely loved it. The booking process was easy and safe. Lesley provided all documentation that I asked for before I sent any money and went out of her way to make sure I was completely comfortable with the process. When we arrived, the cottage was immaculate. The condition of the home was exactly as depicted. The beds were comfortable, the kitchen well stocked and she was available for any questions, concerns and potential problems that could have arisen. I couldn’t have asked for a better experience. We loved the location and the time spent there and will definitely return. Thank you again!" -Denise, 2024

Guest access
Keyless Nest Lock - the codes are changed after each stay for increased security.

Washer • Hangers • HDTV • Essentials • Dryer • Hair dryer • Bed linens • Iron • Hot water • Extra pillows and blankets

Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town District. No car is needed as you can walk to the beaches and all of the famous attractions.

The space
Two of the Queen bedrooms share an en-suite bath easily assessable from either bedroom. It features a very large walk-in shower. The 3rd bedroom features a full sized bed, walk in shower and private entrance. The quaint living room has a new L Shaped Sofa that provides plenty of additional sitting room for kicking back and chill time.

Each bedroom and the living room are equipped with brand new HIDEF Samsung 4K Smart TV’s. In addition, we have recently upgraded the cottage to include FREE 250 Mbps Comcast Hi Speed Business Internet, new orthopedic mattresses, and cozy linens – towels to make your stay relaxed and pleasant. There is also a brand new Central Air Conditioning system to help keep you comfortable and snug, especially during the warmer summer months!

Other things to note
IMPORTANT: We strongly recommend purchasing travel insurance to protect against illness, medical emergencies, weather-related issues, or other unexpected circumstances. While travel insurance can be purchased during the booking process, you may want to consider other reputable travel insurance providers, such as Travel Guard (AIG), Nationwide, Allianz, Berkshire Hathaway and Red Sky. We encourage you to review their coverage options and rates to find the best fit for your needs.

For those traveling during Florida's hurricane season (June 1 – November 30), travel insurance is especially important. Please note that NO refunds will be issued for weather-related disruptions or early departures.

Central air conditioning • Shampoo • Bed linens • Iron • Hot water • Hair dryer • Essentials • Body soap • Hangers • Extra pillows and blankets