The Florida Keys, an archipelago of 800 islands, is the ultimate summer destination. Diving in John Pennekamp Coral Reef State Park to see its amazing marine life is a must. A snorkeling trip to Bahia Honda State Park or a boat tour of Dry Tortugas National Park are also crowd favorites. If you’re visiting with kids, the city of Marathon is the perfect place for you. It has a Turtle Hospital and Dolphin Research Center with hands-on activities for children of all ages. For couples, a romantic sunset cruise in Key West is a great way to spend their evening. Meanwhile, solo travelers will love strolling through the galleries, museums, and cafes on Duval Street. Read on for the top cottages for rent in Florida Keys, Florida.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on March 12, 2024.
1. Cozy cottage with a private dock, Islamorada (from USD 225)
Featuring a private boat dock and ramp, four bicycles, and four kayaks, this waterfront cottage is a perfect summer holiday home. It also has a barbecue grill and a picnic table, perfect for an outdoor get-together with friends and family.
The cottage comes with one bedroom and one bathroom and can sleep up to four guests. The interiors are newly renovated and feature a kitchen with stainless steel appliances and a living room with a flat-screen TV. Wi-Fi and air conditioning are also provided.
Top guest reviews
Amenities & Room:
Downstairs is one bedroom upstairspretty much anything you needHaving a large truck also made it difficult to back boat to slip due to one palm tree which is in line with boat slipThere is a full size kitchen and a washer/dryerbut is was our own private paradiseCleanliness:
Everything was clean and well maintainedThe property was very clean spacious and provided everything we needed for our relaxing vacationLoved our stay so clean and well keptWas newly renovated clean and smelled amazingThe view and location was awesome and secure The property provide a large boat dock and slip which we were excited aboutHost:
Carmen was awesome to work with Always very quick to respond to any questionsThey answered all our questions very quickThey are the absolute best genuine people we have met :)We spoke with Carmen and the neighbors both very nice and welcoming's since she also has a boat rampRead more reviewsLocation:
it has everything you need and in a great locationIslamorada is a beautiful area with delicious restaurants and lots of shopsThe owners Carmen and Pablo are very nice peopleWe're in the keys 3 to 4 times a year and this place has become our first pickThe location is perfect Easy access to the marinas for fishing charters and other attractions Carmen and Pablo
2. Homely cottage with a balcony and back porch, Marathon (from USD 525)
Guests will love the views of the sunset from the spacious balcony and back porch of this waterfront cottage. Guests don’t have to bring any gear with them to fully enjoy the place as the rental comes with free use of kayaks, a ComPac sailboat, and bicycles. Inside, you’ll find comfy furnishings, quirky motifs and art, giving the space a homely vibe.
Ideal for up to eight guests, the cottage offers four bedrooms and two bathrooms. Guests can prepare delectable meals in the fully equipped kitchen and spend quality time together in the living room with a flat-screen TV. Wi-Fi and air conditioning are also provided.
Top guest reviews
Amenities & Room:
terrific location beds were comfy and the small island vibe is terrificRead more reviewsHost:
love this place adorable comfortable friendly hostsbarry jim and pam are the most thoughtful and kind hosts i have ever encountered
3. Paggit House, Key West (from USD 935)
If you’re looking for a home away from home experience, then this three-bedroom, two-bathroom house with a white picket fence is perfect for you. The house is located smack dab in the middle of Old Town, so a stay here will put you within easy reach of local attractions, including Duval Street, South Beach, and Mallory Square.
The rental sleeps up to six guests and comes with a full kitchen for home cooking, a cozy living room with a flat-screen TV, and a spacious dining room. You will be charmed by the outdoor space as it offers a swimming pool that is ideal for a relaxing dip and a patio with a barbecue grill, which is a perfect spot for alfresco dining.
Top guest reviews
Amenities & Room:
the a/c worked very wellplenty of room with good internetalso for the price of our stay we expected more comfortable mattressesthe rooms are all large and fit my family and the pack n play we broughtCleanliness:
very clean and was as described in advertisementsreviewer comments: incredible home and very cleanhome is older but everything was clean and in working conditionHost:
rating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulRead more reviewsLocation:
this is a great property close to everythinglocation location location perfect house for 3 couplesreviewer comments: perfect property for 6 adults and within walking distance to many great locationswhat a great trip and a perfect place to staythe house was definitely walking distance to most attractions (including duval st
4. Waterfront cottage with a large deck, Marathon (from USD 170)
Ideal for a small group, this one-bedroom cottage can sleep four guests. It comes with a fully equipped kitchen, a living room with a flat-screen TV and Netflix, brand-new furniture, a washer and dryer, and Wi-Fi, making it perfect for long-term stays.
Guests staying here will love hanging out on the spacious deck overlooking the channel. They can also bring their boat as the rental has its own dock. For recreation, Sombrero Beach is only 4 miles (6.4 kilometers) away. It’s a great spot for snorkeling, fishing, and lounging on the sandy shores.
Top guest reviews
Amenities & Room:
we enjoyed the comfortable seashore themed ambiencewe enjoyed the screened in porch with the couch and dining tablealso the back patio is very spacious and comfortableCleanliness:
very clean and updatedvery clean and neatperfect clean comfortable couldn’t of been betterthe property was very clean and we'll stockedit was clean comfortable and well stockedHost:
the owners have done an excellent job in a recent remodelvery responsive with any questions about our staywe really enjoyed the kayaks and stand up paddle board the owner was very nice to work withi would highly recommend staying at this house the owners were great and the location was perfectthe owners were always available we had more than we needed we wish we could’ve stayed longerRead more reviewsLocation:
great location that's close to everythinggreat location in the middle of marathonperfect location and great accommodationsgreat central location and nice quiet streetstores close by and plenty of very nice dinning places
5. Well-furnished cottage for couples, Key Largo
This cozy cottage is a good choice for couples who want to spend a romantic time together. It offers a great vantage point for beautiful sunsets and is also located close to “the diving capital of the world,” John Pennekamp Coral Reef State Park. Guests also have access to the community amenities, such as a heated pool, a tennis court, and a basketball court.
For date nights, couples will be happy to know that there are fantastic local restaurants nearby. The cottage offers one bedroom and one bathroom. A full kitchen, a flat-screen TV, air conditioning, a washer and dryer, and Wi-Fi are provided as well.
Key Largo, Florida, United States
97.01 km (60.3 mi) from Bahia Honda State ParkAccommodates: 2
Top guest reviews
Amenities & Room:
a well stocked kitchen (including coffee and spices) and an awesome air conditionerthe cottage was very updated and modern while being home like and cozythe pictures are accurate and there are comfortable beds nice sheets and fluffy towelsthe tv in the living room is large and easy to usethe place is very well stocked with basic kitchen and bathroom suppliesCleanliness:
this place was outstanding it was as clean as clean could begreat communication very clean had a wonderful time in key largowe really appreciated the cleanliness and beauty of the placethe place was spotless and highly comfortablethis place is clean cozy and a great valueHost:
all resort staff were friendly and helpfulthe owner did everything he could to help me and he checked in with me frequentlywonderful totally enjoyed our stay and the host was greatthank you so much eric for being such a great hosteric was a very helpful and gracious hostRead more reviewsLocation:
great restaurants close by toothis place is close to a lot of great restaurants and dive centersthis is a great place for location access to a pool golf-carting around and a friendly cuban neighborhooda wonderful place to stay with so many extras availablethis place is amazing bottle of chilled wine upon arrival with a cute note welcoming you
6. Spacious cottage with harbor views, Marathon (from USD 429)
This three-bedroom cottage has everything you need for a fulfilling and relaxing vacation in the Florida Keys. Situated in the Village at Hawks Cay on Sunset Drive, it offers stunning views of Tom’s Harbor and Duck Key. The cottage is spacious enough to host up to eight guests.
The living room has glass sliding doors and windows that welcome bags of natural light, giving it a bright and airy feel. You can also enjoy movie nights in the living room that comes with a 52-inch TV and surround sound system. When you get peckish, you can cook delicious meals in the full kitchen and enjoy it outside on the back patio.
Top guest reviews
Amenities & Room:
beautiful view comfy beds kitchen equipped wonderful place to rentthe only issue was the toilet in the master bedroom upstairs ran pretty much the whole tripthe 3 bed 3 bath was perfect for 3 couplesthe bedroom with the one queen size bed is pretty tight but still comfortablewe all were comfortable and had space to have some alone time when neededCleanliness:
clean and well appointed condovery clean and welcomingeverything was really clean & well equippedvery nice house clean modern and well keptvery clean throughout beautiful viewsRead more reviewsHost:
the owner was very responsiveproperty owner was easy to work withvery good communication from the owner and very easy to work with
7. Charming oceanfront cottage for six, Cudjoe Key (from USD 570)
Featuring ocean-themed décor and aqua tones, this homely and charming cottage is perfect for families. It has two bedrooms and can accommodate up to six people. Complimentary kayaks and bikes are also graciously provided by the hosts. Guests don’t have to go far to access the water as the property is directly located on the dock.
The cottage also has two bathrooms, a full kitchen with modern appliances and a breakfast bar, a cozy living room with beautiful sea views, and a washer and dryer for your laundry needs. HDTVs and Wi-Fi are also available for indoor entertainment.
Top guest reviews
Amenities & Room:
fantastic views beautiful kitchen and comfortable bedsbeautiful view nice pool and swimming areacommunity pool was great and looked like it was recently re doneCleanliness:
on-site pool was clean and local community was friendlygreat place to stay very nice and cleanwish they weren't so on top of each other but everything was awesome clean and better than expectedbeautiful sunrises lots of amenities great location very clean great communicationatlantis was clean comfortable and beautiful and had just about the most perfect view one could ask forHost:
manuel is a great host answers any questions promptlymanuel & alan were also excellent hostsmanuel is a great hostgreat spot and a great host would recommend to anyone in the lower keys areamanuel was a great host and we would definitely recommendRead more reviewsLocation:
this is a perfect locationproperties are pretty close togetherwhat a wonderful location to watch every sunrisethis is florida keys paradise and this location came as advertisedgreat location perfect for fishing kayaking paddle boarding
8. Tidewater Views, Cudjoe Key (from USD 199)
This bright and airy cottage is the perfect place to spend a summer getaway with friends and family. The cottage sleeps 6 guests, with 2 bedrooms, 2 bathrooms, and over 800 square feet (74.3 square meters) of living space. It provides everything you need for a comfortable stay – a boat dock, kayaks, bikes, and access to community amenities such as a heated swimming pool, tennis courts, and basketball courts.
Inside, you can expect newly remodeled interiors with a full kitchen, a living room, HDTVs in all rooms, a washer and dryer, a barbecue grill, and Wi-Fi.
Top guest reviews
Amenities & Room:
the lagoon area and swimming pool are lovely with a great viewour concierge had music and fans on when we arrived and a sweet welcome giftCleanliness:
the house was beautiful clean updated and spacious for 5 peoplethis place was great super clean and had everything you neededthe grounds are very cleanthe house was clean and very homey with a beautiful viewthe house was cute and clean with lovely complimentary snacks when we arrivedHost:
space had everything that was advertised and the property manager was very responsive and welcomingRead more reviewsLocation:
close to key west peaceful and quietvery clean and nice house perfect location last key was very helpful and accommodating we would definitely rent againbeautiful place for a relaxing getaway
9. Sea Glass Cottage, Tavernier (from USD 350)
Set in a corner lot with a direct bay or ocean access, Sea Glass Cottage is your ideal summer holiday home. This waterfront cottage has two separate docks, so feel free to bring your boats. It is also located in a family-friendly neighborhood and is close to grocery stores and local restaurants.
The cottage features newly remodeled interiors with wood-like floors, ocean-themed décor, comfy furniture, and plenty of natural light. Six people can sleep across its two bedrooms. There’s also a front patio where you can relax and soak up splendid views of sunrises and sunsets.
Top guest reviews
Amenities & Room:
sea glass cottage is a beautiful comfortable very accommodating home with a beautiful viewvery comfortable mattress in master bed room5loved all the decor and finishing touches very comfortable beds and couchsparkling clean great amenities and thoughtfulness in every roomCleanliness:
very clean and nicely decoratedgreat property for boaters super clean and cozygreat house very clean perfect locationthe house was extremely clean inside and out we were really impressedvery clean and denise is a great hostHost:
friendly and helpful hostsawesome place to stay and wonderful owners to deal withdenise and frank were great hostsgreat house and facilities really friendly and helpful ownerthey were responsive to our texts and emailsRead more reviewsLocation:
great location in a nice neighborhoodgreat location seriously very good2the location was easy to find and close to restaurants local dive bars and grocery storesthis place is in the perfect location and it is absolutely beautifulwe loved the location we would stay again without any hesitation
Sun, sand, and surf await in the Florida Keys
The Florida Keys is a world-famous destination for a reason. With pleasant weather year-round, hundreds of miles of beaches and coral reefs, a vibrant local community and exciting nightlife, visitors here are guaranteed a good time. Bookmark this list of our recommended accommodations so you can easily find your summer home on your next trip.
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