Charming Cottages in Islamorada, FL for Your Perfect Getaway

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."

Ocean Front Unit In Islamorada | Enjoy Scenic Walks on Private Beach
Cottage
Islamorada, Florida, USA

Set along a private beach in Islamorada, La Siesta Resort & Villas features colorful cottages with premium amenities. Guests enjoy heated pools, Sidecar poolside bar, water sport rentals, marina access, and shared benefits across three resort properties—including shuttles, dining, and leisure facilities.

✦ Your room is 450 sq. ft, equipped with complimentary toiletries, TV.

✦ Daily cleaning services included in the nightly price.

There are a few additional details to know before you book:

✦ The minimum age required for check-in is 21 years old.

✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.

———————————————

Guest Access:
During your stay, you will have access to the property and amenities according to the following schedule:

✦ Check-in is available from 04:00 pm.

✦ Pool available all year.
Additional features:
• Heated pool

———————————————

Other Things to Note:
There are several additional things to note:

✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.

✦ A mandatory resort fee of $55.13 per night will be collected upon check-in, not included in the daily rate.

✦ Pets are welcome. $50 per pet per day, with a max of 2 pets

✦ There is a 7am-11pm front desk in the building that has the guest's information and keys ready. After these working hours you would be advised to our other sister resorts near by for check in.

Amenities:

Tv • Other • Ocean View • Bedding/Linens • Laundry • Fireplace/Heating • Pet Friendly • Kitchen • Oceanfront • Balcony/Terrace • Security/Safety • Pool

Little Bay Cottage
House
82246 Overseas Hwy, Islamorada, FL, 33036, USA

Little Bay Cottage offers accommodations in Islamorada, 2.1 miles from Theater of the Sea on Islamorada and 2.7 miles from Windley Key. The air-conditioned accommodation is a 13-minute walk from Upper Matecumbe Key. The vacation home provides parking on-site, a spa center, and a 24-hour front desk. With free Wifi, this 2-bedroom vacation home features a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking. A water park is also available for guests at the vacation home. Pigeon Key is 13 miles from Little Bay Cottage, while John Pennekamp State Park is 21 miles from the property. Miami International Airport is 74 miles away.

Amenities:

Oceanfront • Security/Safety • Air Conditioner • View • Fireplace/Heating • Breakfast • Sports/Activities • Wellness Facilities • Guest Services • Parking • Spa • Internet

WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei
Cottage
Islamorada, Florida, USA

1940s Old Keys Fishing Cottage with dockage available. Large Waterfront property and walking distance to world famous Lorelei Cabana Bar & Restaurant as well as local breweries too ! This 1940s original Keys Fishing Cottage is not fancy, as the ad's photos show, but in great location and has everything you need for a great Islamorada getaway. We can arrange custom days of stay if you are booking a sunset/sandbar/fishing charter with our family. Enjoy the peace and privacy of the large, natural waters edge property with the convenience of being minutes away from some of the best dining and outdoor activities in the Florida Keys. Dockage is available on site for additional charge with free trailer storage. Relax in our 1940's "Old Florida Keys" style cottage which is updated while still maintaining its original look and feel ~ Original open beam ceilings and hard wood floors. Wi-Fi . Central air. King size bed in bedroom. There is one bath with original 1940s tile on walls, laundry area with full size washer and dryer. There is a second room that offers a desk for remote work and sitting area as well. We want you to enjoy your experience in the beautiful Florida Keys !! We are lifetime residents and our children born and raised here as well. This property is located conveniently within walking distance or at most ,less than half a mile to most Islamorada restaurants and local breweries. Kayak rentals and paddleboard rental is available for delivery to property. Great area for kayaking and paddle boarding. Launch right from water's edge of property. Please contact me prior to booking with any questions as I always want to make sure that the cottage is a good fit for prospective renters. Dockage is available at property for up to 35' boat for a fee of $50 per day with free trailer parking on premise payable upon arrival. No children please as the property is not fenced along the extensive water frontage and is not suitable. Thanks for checking out our listing :) If you book you will have a great time! *** Dockage Fee of $50 per day payable upon arrival and is NOT included in VRBO reservation fees and can be discounted dependent on length of your stay. You will have a fun time!! One Pet under 20 lbs welcome.. PLEASE ADD TO YOUR RESERVATION WHEN BOOKING. Thanks so much for liking our place ! :)

Guest Reviews:

- "Our stay at Jackie’s home was incredible. The house was extremely clean and cozy. The view from the dock is unbeatable to watch the sun set or see manatees swimming by at all hours of the day. The location feels very private, yet it’s just walking distance from multiple restaurants for breakfast or dinner. We already want to make plans to come back. Jackie was a fantastic host!" - "We LOVED our stay here. As advertised, this is a clean, charming cottage. The location is secluded & peaceful with great waterfront views. We enjoyed watching the iguanas and fish. Great host with great communication! Would definitely stay here again!"

Oceanfront Private Cottage!
Cottage
Islamorada, Florida, USA

Welcome to Paradise Cottage!!

This downstairs portion of a dual family dwelling is fully renovated a 1/1 cottage with breathtaking oceanfront views.
Sleeps four comfortably.
Private bedroom with queen bed.
Living room has two full size futons.
New kitchen with all stainless steel appliances.
Very cozy and great views to enjoy in your dream vacation.
Amenities provided are kayaks, bicycles, grills, boat ramp and boat dockage for your use with no extra fees.

Private boat dock and convenient boat ramp. Amenities for your boat includes water and electricity(only 110volts) by the dock, brush and soap, extra fenders, and a small freezer for bait and ice. Trailer parking is available on our acre and a quarter property. The ramp and dock use are part of the rental amenities!

Relax and enjoy ocean views and gorgeous sunsets from the comfort of our multiple loungers.

Plenty of parking for all of your toys in my acre and a quarter property(boat, trailer, car, etc).

BBQ areas with plenty of seating and a separate picnic table perfect for lunch and snack time.

Bath towels
Bed linens
Hair dryer
Wifi
Cable
TV in living room and bedroom.
Washer and dryer
All appliances in kitchen
Coffee maker (K-cup and drip )
Toaster
Blender
Pots and pans

Close to all attractions and best restaurants.

Those who want to charter a fishing captain upon request please contact Captain Avila or other captains from Whahoo Marina.

Guest Reviews:

- "Nice property and location. Clean, well kept, and fully stocked. Prompt communication." - "We spent ten days there. It was very clean, convenient, and had a beautiful view. Very comfortable." - "My family and I had a great time. The owners of the property were amazing and quick to respond to any inquiry we had. Really could not think of anything more that they could have provided. The home was exceptionally clean and it's location was optimal. Will definitely be booking at this location again. Thanks again for everything Pablo and Carmen! From Roger Reyes."

2BR/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool
Cottage
Islamorada, Florida, USA

Enjoy a unique and secluded vacation experience in the heart of Islamorada at Shady Palms! Our charming cottage features two private bedrooms, a fully stocked kitchen, and a spacious living area that comfortably accommodates up to four guests.

There are many sights to see and activities to enjoy nearby. Within just a mile from our cottage is Islamorada's top-rated attraction, Robbie's Marina, where you can embark on a variety of adventurous activities, including snorkeling, fishing, parasailing, or sunset charters, as well as guided tours by kayak or paddleboard through the mangrove channels encompassing the island's coasts. During your time on the water, you may encounter fascinating marine species, such as manatees, Atlantic bottlenose dolphins, and sea turtles. From the shore at Robbie's Marina, try hand-feeding the massive tarpon and friendly nurse shark species commonly found in our warm, tropical waters.

There's something to please every family member here in the Florida Keys, such as swimming with dolphins and sea lions at Theater of the Sea or learning more about the island's culture and history at the History of Diving Museum. Foodies will also enjoy a range of restaurants serving various dishes, including authentic Cuban and Florida Keys cuisine. Our favorites include Midway Café for delectable breakfasts, baked goods, smoothies, and the best Key Lime Pie Frappé! For dinner, consider reserving a table at Lazy Day's, where you can enjoy a superb ocean view from the comfort of their dining room and an excellent menu selection that will appeal to even the pickiest palettes.

After a fun-filled day traversing the island chain, return home to the comfort of your private vacation home, where you can rest easy and recharge. To help you relax, consider a dip in the communal, heated swimming pool, which is exclusively accessible to the few cottage homes at Shady Palms. Are you planning on doing some boating? Caloosa Cove Marina is just 3 miles south and offers competitive wet slip, trailer storage, and fuel prices.

Guest Reviews:

- "We had the best family vacation! The location is central to great entertainment and restaurants but also secluded enough to be a quiet retreat at night. Loved the pool and the cleanliness of the property! We can’t wait to come back." - "We stayed for just over a week and it was perfect! Clean, easy to access and just what we were looking for. We will definitely book again next year!" - "Exceeded expectations, beautiful place" - "Love it! Such a cute place. New and clean. Loved the pool and proximity to Robbie’s."

Private Cottage on Bayfront Estate – Pool, Beach, and Boating Paradise
Cottage
Islamorada, Florida, USA

Welcome to the Garden View Cottage at Mermaid's Bay Boutique Estate, a serene hideaway located in the heart of Islamorada, just moments from top attractions and restaurants. This secluded estate offers a tranquil escape directly on the bay, featuring 3.5 acres of beautifully landscaped grounds with over 300 feet of bay frontage, protected dockage, and access to a resort-style pool and hot tub.

This charming cottage has been thoughtfully updated while preserving its original Florida Keys character. Screened-in porches shaded by lush tropical landscaping welcome you at both entrances. Inside, the cozy 2-bedroom, 1-bath cottage comfortably sleeps six, featuring a king bed in the master bedroom and two queen beds in the second bedroom. The bathroom, complete with a shower and tub, is located between the two bedrooms.

During your stay, enjoy access to a range of amenities that make this estate feel like a private retreat: a resort-style pool and hot tub, sandy beach area, tiki hut, water-front fire pit, and a spacious boat basin. Whether you’re here to fish, explore the bay, or simply relax, you'll have everything you need, including bikes, kayaks, paddleboards, beach chairs, and more. There’s also a small boat ramp for your convenience.

The Garden View Cottage is equipped with a fully stocked kitchen, linens (including beach towels), a filtered water dispenser, and a grill with complimentary propane. To make your stay effortless, we provide paper towels, toilet paper, coffee, and toiletries to get you started on your vacation.

Rentals are from Friday to Friday, with the possibility of flexible dates upon request. Please note that this is a shared property with two other units, each with their own privacy.

Guest Reviews:

- "Peaceful location and Tony is very responsive." - "This is a cute cottage tucked away on gorgeous grounds. Close to the pool and an amazing view of the sunset. We had some windy days and the pool, which has a gorgeous view of the water, was protected and warm. Tony was responsive and helpful. He provided everything from beach towels to fire wood to have a waterfront fire." - "It’s even BETTER than advertised! We feel So Fortunate to have found Tony’s Place! It is Spotless, Very Private, Peaceful, Plenty of room to move around without running over somebody, On the Water, close to EVERYTHING, Foliage is Beautiful, Heated Pool, Spa and Waterfalls ( especially at night with the Lights) is to Die for. The Cottages and House have been Beautifully Restored and just Complete the Whole WONDERFUL EXPERIENCE of staying there!! And I’m not done, yet! Then there’s TONY! He’s the MAN!! He gets all the CREDIT for doing what it takes to get this Whole Operation up and running! He is EXTREMELY EASY to work with and he will ENSURE YOU that your stay will be what YOU WANT! One last thing. The Keys, the Highway with ALL the traffic, can be a Very Busy place, but, when you Open, Drive thru and the Gate close’s, its all left behind and You’re HOME!! I hope you can GO and ENJOY THE EXPERIENCE! We’ll SEA you there next January and February 🏖🐬🌺👍🍹😎‼️"

Work from home in this slice of Islamorada paradise!
Cottage
Islamorada, Florida, USA

Come visit this tropical, remodeled vacation home and get a taste of all Islamorada has to offer with cozy, modern and clean outdoor and indoor living! Perfect for couples on a romantic getaway, solo-travelers looking for a work-from-home retreat or families enjoying time by the sea together.

This home offers 2 bedrooms, 1 full bath, fully stocked kitchen, living and dining area with plenty of outdoor living space for the whole family. Park in the covered car port and enter your island oasis overlooking the canal. Sit beneath the tiki where you can relax, barbecue and greet passing manatees. Take a nap on one of our hammocks and hear the rustling palm trees sway in the island breeze. Chat over snacks and spirits under the second tiki and bar stools. The outdoor area has 60' of dockage and a fish cleaning table.

Upstairs you'll find a large outdoor deck — fit with another hammock, seating and dining area. Once inside, you'll enter through the living room, which has a nook with bar stools opening into the kitchen. The fully stocked kitchen is fit with stainless steel appliances and an eat-in counter. The dining table expands to comfortably seat four. By the kitchen, overlooking the front driveway is another balcony — perfect for enjoying a morning coffee or afternoon snack. Through the hallway, you'll come across the bathroom, which has a large shower, brand new LG washer-dryer unit and a vanity area. Across from the bathroom is the second bedroom — fit with a bunk bed and tumble for three. The second bedroom has a desk and access to the front balcony, which overlooks the quiet street and front yard. The master bedroom is tucked away at the end of the hall. It has a king bed and attached seating area, perfect for reading a book or working from home. The master bedroom overlooks the backyard and canal.

The home has reliable WIFI connection throughout (even accessible in the backyard); our daughter has consistently worked from home and taken classes remotely via Zoom with the WIFI connection. It is stronger than our internet connection on the mainland. There are smart TV's in all bedrooms and in the living room.

The house is located on a quiet, residential street. The street is dimly lit at night to protect sea turtle hatchlings that may be nearby, making perfect viewing conditions for star gazing.

The home is within walking distance to Anne's Beach (best public beach in Islamorada) or 3 minute drive by car. Across from Anne's Beach is a public fishing bridge on the bayside, which is great for watching sunsets after dinner. The home is also walking distance to Caloosa Cove Marina, where you can rent or charter a boat, grab goodies at the convenience store, or eat Cuban cuisine at Habano's Oceanfront Dining (a must for a South Florida visit!). Bikes available upon request at no extra charge.

This vacation home is not pet friendly. Additionally, no smoking is allowed on premises (inside or outside of house). Unregistered guests are not allowed to stay overnight at the home; reservation is subject to cancellation if unregistered guests are found staying on property. To prevent this, a copy of identification will be required of registered guests before each stay begins. A ring camera is located on exterior of home.

Our family loves Islamorada and has made the best memories on Lower Matecumbe Key and hope The We Key House is the perfect home-base for your trip! Please do not hesitate to reach out with any questions or concerns. We are happy to assist with recommendations on activities and dining nearby.

Guest Reviews:

- "Immacute, comfortable and cozy decor. Well stocked. Lots of outdoor space — tikis, decks and dock. Consider having contact number of local handy man to contact with unforeseen repair needs" - "We had such a relaxing stay at this clean, modern, beachy property. Both inside and outside living areas were comfortable and had every convenience you could think of to make you feel at home. The location was nice - a short walk to 2 restaurants and a bike ride to Anne’s beach. Being on the canal was an added bonus if you like fish or watch nature. The hosts went out of their way to ensure we had a good time - from greeting us upon arrival to texting us recommendations of places to eat ( all of the recommended restaurants were delicious ). If we take another trip to Islamorada we will definitely be staying here. It’s a no brainer!"

Charming cottage on the Florida Bay in the heart of Islamorada with pool, dockage, beach + more
Cottage
Islamorada, Florida, USA

The Bay View Cottage is one of three private homes located at Mermaid's Bay Boutique Estate. Located in the heart of Islamorada, just moments away from top attractions and restaurants, this secluded estate is situated directly on the bay. Secured by a gated entrance, the property sprawls over 3.5 meticulously maintained acres, with over 300 feet of bay frontage, protected dockage, and a resort-style pool and hot tub.

Nestled within one captivating property, our collection of vacation rentals at Mermaid's Bay includes three individual homes, each with their own allure and privacy. The homes may be rented individually or collectively and are available for weekly or longer rentals. (Note: This listing is for booking JUST the Bay View Cottage.)

The original Florida Keys charm has been preserved and tastefully updated throughout this romantic 2/1 '60s era cottage. Two sets of French doors off the open-concept living and dining area offer open-water views of the bay and lead out to a wrap-around porch that is shaded throughout the day by large trees. The cottage sleeps six with a king bed in the master bedroom and two queen beds in the second bedroom. A full bathroom with a shower and tub is located off the hallway.

Shared on the property is a resort-style pool and hot tub, cabana bathroom with private outdoor showers, sandy beach area, shaded tiki hut, water-front fire pit and a large boat basin. Easily access both the bay and ocean from our convenient location to enjoy every type of fishing the "Sport Fishing Capitol of the World" has to offer. Bikes, kayaks, paddle boards, hammocks, beach chairs, umbrellas and more are provided for your enjoyment. A small boat ramp is located on the property.

The cottage has a fully stocked kitchen, personal safe, linens including beach towels, a filtered water dispenser and a grill with complimentary propane. Complimentary paper towels, toilet paper, coffee and toiletries are provided to help you start your vacation.

Complimentary laundry service (wash and fold) at laundromat under the same ownership is provided to all renters. Please note that a washer and dryer is not located in the home.

Rentals are from Friday to Friday. Differing dates may be approved on a case-by-case basis.

Guest Reviews:

- "Everything about the home and surroundings was perfect." - "Excellent offers it all. Close to everything." - "The property is gorgeous. This is a one-of-a-kind compound with approx. 250 feet of ocean frontage. The pool is beautiful, the cottage is so clean and beautifully decorated. Tony keeps the entire property well maintained. A piece of paradise. A truelly wonderful place to spend a vacation." - "This place is incredible! Perfect location, beautiful view and very clean. Our family enjoyed this place so much! Tony was a great host. We will be back!"

Lush tropical plantings in a gated compound located directly on the Florida Bay
Cottage
Islamorada, Florida, USA

PROPERTY NAME: Little Bay Cottage
82246 Overseas Highway, Islamorada, Florida

LOCATION: Cottage located directly on the Florida Bay

MINIMUM STAY: Weekly or Monthly

MILE MARKER: 82.2

DETAILS:
- Located on a one-acre lush tropical setting in a gated compound directly on Florida Bay
- One of 3 separate units for rent by the week or month, each sleeping up to 6 people
- Protected dockage for up to a 34-foot boat
- Sunning area with lounge chairs on the peninsula
- Hammocks, pergola, and tiki for relaxing
- Panoramic views of Florida Bay from the covered balcony
- Spacious interior with 2 bedrooms, 2 bathrooms, and a queen-size sleeper sofa
- Updated kitchen with new appliances and granite countertops

Little Bay's Cottage is a ground-floor home with a unique floor plan. The main living area is in the center of the house, with a kitchen, dining area, sitting area, and full bathroom. To the right is a large bedroom with a king bed and full bathroom. The laundry area with a full-size washer and dryer is also located in this room. To the left of the living area is an enclosed sunroom that can be used as a second bedroom at night. The sofa in the sunroom converts to a queen-size sleeper, and there is also a twin-size Murphy bed. The cottage offers a little more privacy than the duplex units, but it does not have water views.

The three units are available for rent by the week or month. Each unit sleeps up to 6 people, so you can rent one or all of them for a family reunion. Protected dockage in the "little bay" can accommodate boats up to 34 feet long. There is also a sunning area with lounge chairs on the peninsula, as well as hammocks, a pergola, and a tiki hut. All of the units have central air conditioning, a flat-screen TV in the living room, and WiFi.

SLEEPING ARRANGEMENTS: Sleeps 6 comfortably
Primary Bedroom: King Bed, Bathroom with Shower
Guest Bedroom: Queen Sleeper Sofa and Twin Murphy Bed, Bathroom with shower

AMENITIES INCLUDE: Dockage for up to a 34 ft boat, Charcoal grill, Hammocks, Pergola, Swim and Snorkel in the bay. There is also Cable TV, WiFi, washer and dryer, air conditioning and free parking.

ACTIVITIES: Beach, Swimming, Boating, Offshore Fishing, On Shore Fishing, Paddle Boarding, Museums, Wildlife Reserves, Art, Shopping, Historic Tours and Culinary Adventures. Near by, there is John Pennekamp Coral Reef State Park, Theater of the Sea, Robbie's Marina and Islamorada Fishing Pier.

ENHANCED CLEANING, DISINFECTION AND SANITIZATION: Our number one priority is the wellbeing and safety of our guests. We have contactless check-ins and check-outs. Our properties are cleaned and sanitized by professionally trained and equipped housekeepers who provide quality service, security and personal accountability. We use CDC housekeeping protocols, approved disinfectants and personal protection equipment. Our properties are private, well maintained, hygienic and sanitized. A whole safe and private space just for you and your family.

Amenities:

Fireplace/Heating • Security/Safety • Sports/Activities • Wellness Facilities • Laundry • Balcony/Terrace • Bedding/Linens • Oceanfront • Tv • Kitchen • Other • Ocean View

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
Cottage
Islamorada

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. Each unit is private, and the neighborhood is tucked off the beaten path. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! A 5% lodging tax will be charged on arrival.

Amenities:

Outdoor shower • Conditioner • Body soap • Hangers • Hot water • Cleaning products • Bed linens • Shampoo • Essentials • Hair dryer

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
Cottage
Islamorada

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! Unfortunately, we do not have spare slips for private boats at this time. A 5% lodging tax will be charged on arrival.

Amenities:

Iron • Dryer • TV • Hot water • Essentials • Washer • Hangers • Air conditioning • Shampoo • Body soap

Waterfront Cottage Walk to World Famous Lorelei
Cottage
Islamorada

Waterfront Conch Cottage with Dockage. Short walk to world famous Lorelei for sunset celebrations.
Great location for kayaking & paddleboarding. Custom length of stays can be arranged if booking a sandbar/fishing charter with our family. The fishing cottage built in the 1940s is not fancy, as photos show, but in the heart of Islamorada!
Dockage available for additional $25 per night fee not included in nightly rate. Free trailer storage on site. Pet friendly :) 1 pet under 20 lb $150 fee.

The space
The cottage is located on a large, double lot located directly on the water on Gulf side of the Keys. Dockage is available on site for $50 per night fee that is separate fee payable upon arrival. Plenty of trailer storage on property.

Guest access
The cottage is a vacation rental only. You will be the only guests at the cottage. Great place to bring your paddleboards and kayaks. Launch right from house.

Other things to note
There is NO fishing from the dock ! There are manatees and lots of wildlife in basin therefore we prohibit fishing. We are sorry for this rule but it does help the small fish , manatees and sea birds that reside in our basin. Thanks for understanding :)

FLOATING WATERFRONT 2 BD, 1 BATH COTTAGE MANATEE
Cottage
Islamorada

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. Each unit is private, and the neighborhood is tucked off the beaten path. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! A 5% lodging tax will be charged on arrival.

Amenities:

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

Floating 2 BD, 1 BATH Private Villa Pirates Lair
Cottage
Islamorada

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. Each unit is private, and the neighborhood is tucked off the beaten path. On site, you will have the luxury of renting your own private boat. Boat rentals are discounted for our guests.

Amenities:

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

Stop searching, this is your Slice of Paradise!
Cottage
Islamorada

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

The space
The cottage has 2 bedrooms and 1 bathroom. Both bedrooms offer a queen size bed and the living room also offers a pull out full size sleeper. A full kitchen with stove, microwave, Keurig mini coffee maker, fridge, freezer and ice machine.

Guest access
The cottage will be yours for your entire stay and you will also have access to a stunning heated pool and a communal ramp to launch kayaks or paddle boards. (Kayaks available to rent nearby, 2 stand up paddle boards located at the cottage)

Other things to note
When staying at Key Lime Cottage you are in a prime location. We will provide you with free access to the gem of Islamorada, Founders Park, 15 minute drive where you will find a gorgeous beach, swimming pool with splash pad, a boat ramp and soccer fields and then just 5 minutes south is the newly finished Annes Beach.
Islamorada also offers a free electric ride service called Freebee. (Info on the app is in the welcome pack) the 3 available vehicles can take you anywhere between Mile marker 72 to mile marker 90.

Marathon is 30 minutes south and Key West is around 1hr 40 minutes south.
The location of the cottage will let you explore as much of the keys as you want or if you just want to sip key lime coladas on your porch it allows for that aswel. We are looking forward to sharing this slice of Islamorada with you and feel free to ask for any recommendations or local discounts for fishing trips, dive or scuba excursions, dining, shopping, galleries and more!

Serene Cozy Cottage in Islamorada with Heated Pool
Cottage
Islamorada

Enjoy a secluded vacation experience in the heart of Islamorada at Shady Palms! Our charming cottage home features two private bedrooms, a fully stocked kitchen, and a spacious living area to accommodate up to 4 guests comfortably. After a fun-filled day traversing the island chain, return to the comfort of your private vacation home to rest and recharge, or take a dip in the communal, heated swimming pool, which is exclusively accessible to the few cottage homes at Shady Palms.

The space
Unfortunately, the property owner of this condominium is highly allergic to animal dander, therefore, will not allow the occupancy of any animals.
No campers or boat trailers allowed in the neighborhood. They will have to be stored elsewhere.
The cottage is at mile marker is 76.7
Caloosa Cove Marina located at MM 73.5 is a great choice for slip space, fuel, and trailer storage.
Robbie's Marina is also another one.
Pack n play crib and highchair available must give 48-hour notice before arrival

Villa comes with a “Starter Pack” which includes: 1 backup roll of toilet paper per bathroom, 1 set towels & bed linens, 6 pool towels in linen closet, 1 single box washing machine detergent, 1 roll paper towel, 2 kitchen trash can bags, 2 tablets dishwashing machine soap, 1 small bottle liquid dish soap, 1 set of bath amenities per full bath (shampoo, conditioner, bath gel, lotion, bar soap). For additional supplies during your stay there is a Publix supermarket located within minutes

Guest access
Parking for 2 cars in the driveway only. No boats or trailers, please.

Other things to note
**PLEASE NOTE** If you have booked your reservation prior to August 2nd, 2020, as a guest with KeysCaribbean, we are required to collect the Local Bed Tax/Tourist Tax of 5% of Unit Rental charges. Once you have booked your reservation, we will send an additional payment request through Airbnb for collection of the additional local tax once your reservation is paid in full. This amount should be paid no later than 2 weeks or 14 days prior to your arrival date. This Vacation Rental is a privately owned home and we trust that you will treat the property as if it were your own.

“KeysCaribbean serves as a third party administrator for each property listed herein. KeysCaribbean does not own, lease, or operate any of the properties listed herein. To that extent, KeysCaribbean is not privy to accessibility options for any of the properties listed. For accessibility options and information, please contact us and we will attempt to answer specific questions once we have consulted with the respective properties’ owners."

“Please note that you are required to sign in acknowledgement of several important notices and rules you must abide by during your stay with us within 72 hours of reservation. In addition, Monroe County regulation requires you to provide the names and ages of each occupant as well as information on your vehicle(s) at least 48 hours prior to your stay with us and before you are permitted access to the premises. You will receive two separate links to each of the required forms via text and/or email.”

Islamorada bungalow 2 bed & pool
Cottage
Islamorada

Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp.
If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you.
Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

Amenities:

Body soap • Essentials • Shower gel • Conditioner • Hair dryer • Free dryer – In unit • Cleaning products • Hot water • Shampoo • Free washer – In unit

Enjoy Tropical Experience in Beachfront Casita
Cottage
Islamorada

Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. Hurricane Monument & Indian Key Historic State Park are a few miles away.

The space
✦ Your room is 450 sq. ft, equipped with complimentary toiletries, TV.

✦ Daily cleaning services included in the nightly price.

There are a few additional details to know before you book:

✦ The minimum age required for check-in is 21 years old.

✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.

Guest access
During your stay, you will have access to the property and amenities according to the following schedule:

✦ Check-in is available from 4:00PM.

✦ Pool is available.

Other things to note
There are several additional things to note:

✦ A valid credit or debit card is required for the refundable security deposit and any offline fees displayed upon completing your Airbnb reservation.

✦ Pets are welcome. $50 per pet per day, with a max of 2 pets

Amenities:

Dryer • Essentials • Hair dryer • Air conditioning • Iron • Hangers • Shampoo • TV • Extra pillows and blankets • Bed linens

Islamorada Cottages on the Map

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

Property Name Address Price ($) Star Rating Review Count Book
Key Lime Cottage in the heart of Islamorada 76777 Overseas Highway, Islamorada, FL, FL 33036 308 4.0 9.3 3 Click here
Ocean Front Unit In Islamorada | Enjoy Scenic Walks on Private Beach Islamorada, Florida, USA 730 2.0 1 Click here
Little Bay Cottage 82246 Overseas Hwy, Islamorada, FL, 33036, USA 550 1 Click here
WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei Islamorada, Florida, USA 323 10.0 129 Click here
Oceanfront Private Cottage! Islamorada, Florida, USA 269 10.0 110 Click here
2BR/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool Islamorada, Florida, USA 346 9.6 62 Click here
Private Cottage on Bayfront Estate – Pool, Beach, and Boating Paradise Islamorada, Florida, USA 739 10.0 18 Click here
Work from home in this slice of Islamorada paradise! Islamorada, Florida, USA 282 9.8 14 Click here
Charming cottage on the Florida Bay in the heart of Islamorada with pool, dockage, beach + more Islamorada, Florida, USA 991 10.0 13 Click here
Lush tropical plantings in a gated compound located directly on the Florida Bay Islamorada, Florida, USA 649 1 Click here
FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO Islamorada 200 9.52 1 Click here
1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON Islamorada 200 9.54 1 Click here
Waterfront Cottage Walk to World Famous Lorelei Islamorada 225 9.92 1 Click here
FLOATING WATERFRONT 2 BD, 1 BATH COTTAGE MANATEE Islamorada 299 9.66 1 Click here
Floating 2 BD, 1 BATH Private Villa Pirates Lair Islamorada 299 9.46 1 Click here
Stop searching, this is your Slice of Paradise! Islamorada 321 9.94 1 Click here
Serene Cozy Cottage in Islamorada with Heated Pool Islamorada 335 9.56 1 Click here
Islamorada bungalow 2 bed & pool Islamorada 375 9.94 1 Click here
Enjoy Tropical Experience in Beachfront Casita Islamorada 50000 10.0 1 Click here

Note: The prices for each Cottages in Islamorada 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 Islamorada that include a pool or hot tub include:

  • Key Lime Cottage in the heart of Islamorada.- Review Count: 3, Rating: 9.3
  • Ocean Front Unit In Islamorada | Enjoy Scenic Walks on Private Beach.- Review Count: 0, Rating: 0.0
  • 2BR/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool.- Review Count: 62, Rating: 9.6

These cottages in Islamorada offer spa or wellness amenities:

  • Little Bay Cottage.- Review Count: 0, Rating: 0.0

Family-friendly cottages in Islamorada include:

  • Key Lime Cottage in the heart of Islamorada.- Review Count: 3, Rating: 9.3
  • Ocean Front Unit In Islamorada | Enjoy Scenic Walks on Private Beach.- Review Count: 0, Rating: 0.0
  • Little Bay Cottage.- Review Count: 0, Rating: 0.0

Pet-friendly cottages in Islamorada include:

  • Ocean Front Unit In Islamorada | Enjoy Scenic Walks on Private Beach.- Review Count: 0, Rating: 0.0
  • WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei.- Review Count: 129, Rating: 10.0
  • Oceanfront Private Cottage!.- Review Count: 110, Rating: 10.0

Cottages in Islamorada that include breakfast or meal options include:

  • Little Bay Cottage.- Review Count: 0, Rating: 0.0

Cottages in Islamorada offering on-site parking include:

  • Key Lime Cottage in the heart of Islamorada.- Review Count: 3, Rating: 9.3
  • Ocean Front Unit In Islamorada | Enjoy Scenic Walks on Private Beach.- Review Count: 0, Rating: 0.0
  • Little Bay Cottage.- Review Count: 0, Rating: 0.0

Some of the best Cottages in Islamorada are:

  • Key Lime Cottage in the heart of Islamorada.- Review Count: 3, Rating: 9.3
  • Ocean Front Unit In Islamorada | Enjoy Scenic Walks on Private Beach.- Review Count: 0, Rating: 0.0
  • WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei.- Review Count: 129, Rating: 10.0

Some of the popular Cottages in Islamorada are:

  • WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei.- Review Count: 129, Rating: 10.0
  • Oceanfront Private Cottage!.- Review Count: 110, Rating: 10.0
  • 2BR/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool.- Review Count: 62, Rating: 9.6