Cozy Cottages in Florida Keys

Best Cottage Rentals in Florida Keys

Experience the beauty of Florida Keys with our selection of delightful cottages, perfect for travelers seeking tranquility and style. Each listing promises a unique getaway experience.

Cottages in Florida Keys
The Butterfly Cottage
House
443 97th Street, Marathon, FL, FL 33050, USA

30 miles from Upper Matecumbe Key in Marathon, The Butterfly Cottage features accommodations with access to a hot tub. The air-conditioned accommodation is 1.1 miles from Florida Keys Aquarium Encounters, and guests can benefit from on-site private parking and complimentary Wifi. The accommodation offers a shared kitchen and private check-in and check-out for guests. Providing a terrace and sea views, the spacious vacation home includes 3 bedrooms, a living room, cable flat-screen TV, an equipped kitchen, and 2 bathrooms with a walk-in shower and a hot tub. Guests can take in the views of the garden from the patio, which also has outdoor furniture. The vacation home offers bed linen, towels, and laundry service. For guests with children, the vacation home provides an indoor play area and outdoor play equipment. Guests can also relax in the garden or in the shared lounge area. Captain Hook S Marina Dive Center is 1.1 miles from The Butterfly Cottage, while A Deep Blue Dive Center is 1.9 miles away. Key West International Airport is 49 miles from the property.

Guest Reviews:

- "One word…. Perfect!" - "Absolutely loved the home and the stay. Would love to stay there again!" - "Highly recommend this property!!" - "Very pleasant. Loved the butterfly garden, as well as the overall landscaping. Beach chairs, Bikes +" - "We had a great stay and would return again" - "We absolutely loved it especially the nature in the garden." - "Best anniversary trip!" - "It was convenient and affordable."

Cottages in Florida Keys
Tropical Cottages
Cottage
243 61st Street Gulf, Marathon, FL, 33050, USA

While you're here, you can enjoy all the comforts of home and more, including a garden and daily housekeeping, as well as a picnic area and multilingual staff.

Guest Reviews:

- "Awesome, cozy, relaxing cottages and set up. Perfect location for everything! Thanks, We'll be back!" - "The cottages were so comfortable and cute. The staff were very friendly." - "Very clean and adorable. Quiet, love the Tiki and food truck, and Andrew was nice, and helpful. Coffee in the rooms would be nice, tho, since there are coffee pots. " - "The staff are great communicators and very respectful and friendly!" - "Great people running the place"

Cottages in Florida Keys
NAUTILUS.ocean front cottage retreat ~
Villa
701 Spanish Main Drive, Cudjoe Key, FL, FL 33042, USA

Providing a garden, NAUTILUS...ocean front cottage retreat ~ features accommodations in Cudjoe Key. This beachfront property offers access to tennis at the tennis court, free private parking, and free Wifi. The villa provides a pool with sea views, hot tub, and full-day security. The air-conditioned villa consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a hot tub and a hair dryer. Towels and bed linen are featured in the villa. For added privacy, the accommodation features a private entrance. A mini-market is available at the villa. For guests with children, the villa offers kids pool. Snorkeling, fishing, and canoeing are possible within the area, and NAUTILUS...ocean front cottage retreat ~ offers a private beach area. Ernest Hemingway Home and Museum is 23 miles from the accommodation, while Duval Street is 23 miles away. The nearest airport is Key West International Airport, 21 miles from NAUTILUS...ocean front cottage retreat ~.

Guest Reviews:

- "5 stars" - "This property was perfect wellLoved that it was on the water. Kayaking to near by islands was fun. We saw a lot of wild" - "Great place close to Key West" - "Fantastic!" - "We had a great time with my family" - "There is some confusion with Booking.com and how payment is done. However, Manuel and the property manager are very help" - "Perfect location cute home!" - "We had an amazing stay and everyone had a great time."

Cottages in Florida Keys
Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub!
Cottage
1800 Atlantic 108A, Key West, FL, 33040, USA

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.

Guest Reviews:

- "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."

Cottages in Florida Keys
Key Lime Cottage in the heart of Islamorada
House
76777 Overseas Highway, Islamorada, FL, FL 33036

Key Lime Cottage in the heart of Islamorada offers accommodations in Islamorada, 1.6 miles from Sea Oats Beach and 5.3 miles from Upper Matecumbe Key. This property offers access to a terrace and free private parking. Outdoor seating is also available at the vacation home. This air-conditioned 2-bedroom vacation home comes with a seating area, a satellite flat-screen TV, and a fully equipped kitchen with an oven. Towels and bed linen are provided in the vacation home. For added privacy, the accommodation features a private entrance. Guests can enjoy the outdoor swimming pool and garden at Key Lime Cottage in the heart of Islamorada. Theater of the Sea on Islamorada is 7.8 miles from the accommodation, while Windley Key is 8.4 miles away. Key West International Airport is 74 miles from the property.

Guest Reviews:

- "If you can sustain in a cottage style design, then your stay will be worth it."

Cottages in Florida Keys
Tranquility by Avantstay Close to Duval St w/BBQ & Shared Pool
Cottage
714-5 Olivia St, Key West, FL, 33040, USA

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.

Guest Reviews:

- "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!"

Cottages in Florida Keys
Atocha Cottage by Brightwild
Apartment
614 Greene St, Key West, FL, 33040, USA

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.

Amenities:

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

Cottages in Florida Keys
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Cottage
1075-29 Duval Square, Key West, FL, 33040, USA

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.

Guest Reviews:

- "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. "

Cottages in Florida Keys
Cottage by the Pool by AvantStay w Balcony BBQ Shared Pool Month Long Stays Only
House
Stock Island, FL, USA

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.

Amenities:

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

Cottages in Florida Keys
Cozy Key West Beach Cottage: Walk to Beaches!
Cottage
2623 Flagler Ave, Key West, FL, 33040, USA

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.

Amenities:

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

Cottages in Florida Keys
The Conch-Out Cottage
House
Key West, FL, USA

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.

Amenities:

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

Cottages in Florida Keys
Old Wooden Bridge Resort and Marina
Cottage
1791 Bogie Drive, Big Pine Key, FL, 33043, USA

While you're here, you can enjoy all the comforts of home and more, including a fenced pool and a full-sized refrigerator/freezer, as well as a stovetop and free WiFi. Other amenities include towels, a picnic area, a dining area, and housekeeping.

Guest Reviews:

- "Remote and plenty of dark sky." - "We love the place!! " - "Amazing stay in a boat!" - "Friendly staff. Property as described." - "Love this place and the staff. Friendly and helpful and the area is relaxing and beautiful " - "Staff was friendly and accommodating. Will definitely book again next vacation." - "Very pleasant and relaxing atmosphere." - "The cottage was in great condition and had everything for a great stay! Had fun connecting with Tiffany and exploring Marathon, FL!"

Cottages in Florida Keys
Cayman Cottage
House
Summerland Key, FL, USA

Cayman Cottage offers accommodations in Summerland Key, 28 miles from Duval Street and 28 miles from Southernmost Point. The air-conditioned accommodation is 28 miles from Ernest Hemingway Home and Museum. Free Wifi is available throughout the property and Florida Keys Aquarium Encounters is 27 miles away. The vacation home features 3 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 offers sea views. Key West Aquarium is 28 miles from Cayman Cottage, while Mallory Dock is 28 miles from the property. Key West International Airport is 25 miles away.

Amenities:

Barbecue/Outdoor Cooking • Internet • Laundry • Security/Safety • Child Friendly

Cottages in Florida Keys
TROPICAL COTTAGE by RENT KEY WEST VACATIONS - Quiet & gated. Pool/Deck/Pet frien
Cottage
Key West, Florida, USA

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.

Guest Reviews:

- "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."

Cottages in Florida Keys
Boat House by AvantStay Character Cottage Central Location w Shared Pool Month Long Stays
House
Key West, FL, USA

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.

Amenities:

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

Cottages in Florida Keys
Truly sitting right on the ocean. Ocean's Edge has forever ocean views.
Cottage
Cudjoe Key, Florida, USA

Don’t be fooled by canal front listings. Lose yourself in the ever changing beauty of the Atlantic Ocean in this charming, recently renovated 2 bedroom cottage with large living area and open floor plan. Bring your boat and keep it steps away from your back door on the 52 foot seawall. The cottage sleeps 6 with a king bedroom, twin over full bunk room and a queen size Murphy Bed in the living room for those who want to wake up with a beautiful sunrise view. There is a double kayak, paddle boards at the unit for those who want to explore the Venture and Out Keys that you can see from the living room. Floats, life jackets and a swim ladder and bikes are also onsite. After your ocean fun, rinse off in the solar shower located outside. There is a washer and dryer in the unit as well as coin laundry at the bathhouse which is a short walk away. Each bathhouse also has several showers for guest use. Venture Out Resort has a 24 hour security, large pool, hot tub, picnic tables, tennis courts, pickleball courts, playground, boat ramp and a marina store with fuel, groceries and tackle.

The resort collects it's own $125 fee at the gate when you check in. This fee is per stay and you do not pay it again no matter how long you are renting. This is separate from the cottage rental fees and covers the resort amenities. A parking permit will be issued at the gate while you are renting the house and you can pay a nightly storage fee for boat/ trailer or extra vehicles storage in the overflow parking lot.

Guest Reviews:

- "We will absolutely stay here again! Beautiful, clean and great location for fishing, or just boating! Everything you need is within close reach! And drinks in the fridge! Thanks for the stay!!! G and K" - "We stayed here for our honeymoon. You can’t beat the views here! The house itself was very clean and nice. We spent most of our time paddle boarding, fishing, and swimming right in front of the house! The host is very helpful and responds fast. We hope to be back one day! "

Cottages in Florida Keys
Flamingo Palms Cottage
House
480 27th Street Ocean, Marathon, FL, FL 33050, USA

Featuring a garden, Flamingo Palms Cottage offers accommodations in Marathon. This property offers access to a terrace and free private parking. Captain Hook S Marina Dive Center is 4.7 miles away and A Deep Blue Dive Center is 5.4 miles from the vacation home. With free Wifi, this 1-bedroom vacation home features a cable flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Guests can take in the views of the sea from the patio, which also has outdoor furniture. For added privacy, the accommodation features a private entrance. Florida Keys Aquarium Encounters is 4.6 miles from the vacation home, while Seven Mile Bridge is 1.7 miles from the property. Key West International Airport is 45 miles away.

Amenities:

Barbecue/Outdoor Cooking • Sports/Activities • Internet • Air Conditioner • Oceanfront • Parking • Guest Services • Balcony/Terrace • Other • View • Security/Safety • Ocean View

Cottages in Florida Keys
PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
Cottage
Key West, Florida, USA

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.**

Guest Reviews:

- "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."

Cottages in Florida Keys
Conch Cottage
House
Marathon, FL, USA

Conch Cottage offers accommodations in Marathon, a 6-minute walk from Sombrero Beach and 5.1 miles from Florida Keys Aquarium Encounters. Among the facilities at this property are an ATM and a tour desk, along with free Wifi throughout the property. Guests can request massage treatments or swim their cares away in the outdoor swimming pool. Featuring a balcony with sea views, this vacation home also comes with a satellite TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 3 bathrooms with a bidet and a hair dryer. For added privacy, the accommodation features a private entrance. Captain Hook S Marina Dive Center is 5.1 miles from the vacation home, while Seven Mile Bridge is 5.2 miles from the property. Key West International Airport is 49 miles away.

Amenities:

Wellness Facilities • Internet • Pool • Security/Safety • Sports/Activities • Breakfast • Pet Friendly • Child Friendly • Guest Services • Fireplace/Heating

Cottages in Florida Keys
Heart of Downtown Key West Cottage With Off-Street Parking
Cottage
Key West, Florida, USA

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.

Guest Reviews:

- "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!!!"

Florida Keys Family Friendly Cottages

Florida Keys Cottages with Parking

Florida Keys Pet Friendly Cottages

Florida Keys Cottages with Entertainment

Florida Keys Cottages with Private Pool

Florida Keys Cottages with Private Beach

Florida Keys Cottages with Spa

Florida Keys Cottages on the Map

Compare the Best Cottages in Florida Keys – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
The Butterfly Cottage 443 97th Street, Marathon, FL, FL 33050, USA 274 4.0 9.5 29 Click here
Tropical Cottages 243 61st Street Gulf, Marathon, FL, 33050, USA 101 3.0 8.6 901 Click here
NAUTILUS.ocean front cottage retreat ~ 701 Spanish Main Drive, Cudjoe Key, FL, FL 33042, USA 908 4.0 9.2 16 Click here
Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub! 1800 Atlantic 108A, Key West, FL, 33040, USA 462 3.0 10.0 5 Click here
Key Lime Cottage in the heart of Islamorada 76777 Overseas Highway, Islamorada, FL, FL 33036 308 4.0 9.3 3 Click here
Tranquility by Avantstay Close to Duval St w/BBQ & Shared Pool 714-5 Olivia St, Key West, FL, 33040, USA 404 3.0 9.0 4 Click here
Atocha Cottage by Brightwild 614 Greene St, Key West, FL, 33040, USA 1032 4.0 4.5 2 Click here
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool! 1075-29 Duval Square, Key West, FL, 33040, USA 467 3.0 8.0 2 Click here
Cottage by the Pool by AvantStay w Balcony BBQ Shared Pool Month Long Stays Only Stock Island, FL, USA 166 4.0 1 Click here
Cozy Key West Beach Cottage: Walk to Beaches! 2623 Flagler Ave, Key West, FL, 33040, USA 676 3.0 1 Click here
The Conch-Out Cottage Key West, FL, USA 215 4.0 1 Click here
Old Wooden Bridge Resort and Marina 1791 Bogie Drive, Big Pine Key, FL, 33043, USA 308 2.0 8.6 271 Click here
Cayman Cottage Summerland Key, FL, USA 247 4.0 1 Click here
TROPICAL COTTAGE by RENT KEY WEST VACATIONS - Quiet & gated. Pool/Deck/Pet frien Key West, Florida, USA 692 2.0 10.0 18 Click here
Boat House by AvantStay Character Cottage Central Location w Shared Pool Month Long Stays Key West, FL, USA 248 4.0 1 Click here
Truly sitting right on the ocean. Ocean's Edge has forever ocean views. Cudjoe Key, Florida, USA 478 2.0 10.0 8 Click here
Flamingo Palms Cottage 480 27th Street Ocean, Marathon, FL, FL 33050, USA 302 4.0 1 Click here
PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest Key West, Florida, USA 1125 10.0 226 Click here
Conch Cottage Marathon, FL, USA 575 4.0 1 Click here
Heart of Downtown Key West Cottage With Off-Street Parking Key West, Florida, USA 407 10.0 142 Click here

Note: The prices for each Cottages in Florida Keys do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Cottages in Florida Keys that include a pool or hot tub include:

  • NAUTILUS.ocean front cottage retreat ~.- Review Count: 16, Rating: 9.2
  • Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub!.- Review Count: 5, Rating: 10.0
  • Key Lime Cottage in the heart of Islamorada.- Review Count: 3, Rating: 9.3

These cottages in Florida Keys offer spa or wellness amenities:

  • Blue Water Cottage Villa 5110.- Review Count: 3, Rating: 9.0

Family-friendly cottages in Florida Keys include:

  • The Butterfly Cottage.- Review Count: 29, Rating: 9.5
  • Tropical Cottages.- Review Count: 901, Rating: 8.6
  • NAUTILUS.ocean front cottage retreat ~.- Review Count: 16, Rating: 9.2

Pet-friendly cottages in Florida Keys include:

  • The Butterfly Cottage.- Review Count: 29, Rating: 9.5
  • Atocha Cottage by Brightwild.- Review Count: 2, Rating: 4.5
  • The Conch-Out Cottage.- Review Count: 0, Rating: 0.0

Cottages in Florida Keys that include breakfast or meal options include:

  • Conch Cottage.- Review Count: 0, Rating: 0.0
  • Courtney's Place Historic Cottages & Inns.- Review Count: 1291, Rating: 8.8
  • The Cozy Little Cottage.- Review Count: 15, Rating: 9.4

Cottages in Florida Keys offering on-site parking include:

  • The Butterfly Cottage.- Review Count: 29, Rating: 9.5
  • Tropical Cottages.- Review Count: 901, Rating: 8.6
  • NAUTILUS.ocean front cottage retreat ~.- Review Count: 16, Rating: 9.2

Some of the best Cottages in Florida Keys are:

  • The Butterfly Cottage.- Review Count: 29, Rating: 9.5
  • NAUTILUS.ocean front cottage retreat ~.- Review Count: 16, Rating: 9.2
  • Key Lime Cottage in the heart of Islamorada.- Review Count: 3, Rating: 9.3

Some of the popular Cottages in Florida Keys are:

  • Courtney's Place Historic Cottages & Inns.- Review Count: 1291, Rating: 8.8
  • Tropical Cottages.- Review Count: 901, Rating: 8.6
  • Tropical Cottages.- Review Count: 350, Rating: 8.0