Florida Keys is in the southernmost part of the US, an archipelago in Florida that’s so different from the nightlife of Miami and the theme park adventures of Orlando. Come to this dreamy destination for travelers to experience a true escape from the city. Cherish living amidst nature at glamping spots in Florida Keys. Key West is about 4 miles (6.4 km) long and famous for its watersports, white sandy beaches, lively nightlife, and conch-style buildings and houses. The best time to visit and enjoy the breathtaking natural beauty of Key West is during winter or spring when it’s not raining during the hurricane season.
This island chain is well-known for being a boon for any traveler looking to try stand-up paddle boarding or kayaking among the abundant mangroves. With five distinct destinations, there is bound to be enough to discover here. Visit Key Largo’s John Pennekamp Coral Reef State Park or enjoy deep-sea fishing at Islamorada. Marathon also has wonderful communities such as Key Colony Beach and Sombrero Beach. If you’re seeking more adventures, you may want to explore the several little islands of The Lower Keys. For a more relaxing trip, you may also go to Key West Aquarium or dine at one of the island’s delectable restaurants. Enjoy a relaxing time at a vacation rental or a beachfront cottage in Florida Keys, and be sure to book early, especially if you’re going during the tourist season. Scroll down to find out about the top vacation rentals in Florida Keys, USA.
What to look forward to:
- Civil war buffs will love visiting Fort Zachary Taylor Historic State Park, which has the largest cache of armaments from the war in the world. Visitors can tour Fort Zachary Taylor, watch historic demonstrations, or watch for gorgeous birds.
- Bahia Honda State Park is famous for its amazing views, sunsets, pristine beaches, and bird-watching opportunities. You can also rent kayaks and snorkeling gear for some water adventure.
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 October 30, 2025.
1. Private mini resort, Key West (from USD 3806)
Best for: Reunions, group trips
If you’re a big group looking for a house in Key West, book the Real World MTV House for your trip! With 10 bedrooms, 14 plasma TVs, a pool table, a tennis court, a basketball court, a gym, paddle boards, kayaks, and bikes, and 500 meters (0.31 miles) of oceanfront, there is something for everyone at this house rental in Florida Keys. Plus the house is located far away from downtown and the crowds but near enough that it’s still easy to access.
It’s the idyllic hideaway for reunions, birthday trips, and celebrations so make sure to bring the entire family or circle of friends on your trip.
Key West, Florida, United StatesSuperhost
Accommodates: 16
Top guest reviews
Host:
andrew is a great host and communicates everything to make sure expectations are alignedthe owner/host knows everyone in town so is able to help make your vacation dreams come truearic the house manager was great to work with and very accommodating to our questionsthe hosts were very communicative prompt and laid out all expectations easily for usandrew and his grounds person were very welcoming and helpfulLocation:
the neighborhood is beautiful quiet and fairly convenient to downtown key westgreat location if your group wants to stay in a lotgreat location great amenities great servicehopefully we can get back to this place sooner then laterit is the perfect place to celebrate with a big groupRead more reviewsAmenities & Room:
the house was very comfortable and had everything we needed and more
2. Treetop loft, Key Largo (from USD 224)
Best for: Group stays, nature lovers
Located inside a gated community, this treetop vacation rental in Key Largo, Florida lets you enjoy beach vacations by putting you close to nature. The treetop apartment rental is on the second floor of the main house with its own entrance. It’s an open-floor property with French doors, a mini kitchen, a living area with a TV and a sleeper sofa, and an outdoor deck.
The estate also has a spot where you can sunbathe plus a swimming lagoon with calm water. You can also enjoy an array of activities in the waters as there are rentable kayaks, paddle boards, and snorkels within the vicinity.
Key Largo, Florida, United StatesAccommodates: 4
Top guest reviews
Host:
the instructions and tips provided were very detailed and the owner had some nice recommendations for foodhost is friendly and helpfulleslie was a wonderful host and responded quickly to questionsbeautiful place and hosts kind and hospitablethe owner had christmas decorations during this time making place look all the more beautifulLocation:
the location was great very close to the waterthis is a lovely locationreally nice location for swimming and enjoying the sunsetgreat location and best value on key largogreat location and beautiful property on the waterCleanliness:
our room was very cleanquick communication with host cleanthe apartment was very neat clean private and peacefulthis could be a nice space if cleaned and fixed uproom was just as described and cleanRead more reviewsAmenities & Room:
it was spacious comfortable and had an incredible sitting space on the deck in the tree topstree tops apt is a great place if you are looking quiet and serenitya very nice place at the sea where you can borrow kayaks and relax on sun bedsvery spacious immaculate well furnished tree tops apartment nice outside space though maybe a little smallcozy bed and yes yummy pillows ;) fully equipped kitchen and everything you need in the bathroom
3. One-bedroom apartment with bay views, Key Largo (from USD 320)
Best for: Couples
This one-bedroom apartment located in the heart of Anglers Park has one bedroom with Florida Bay views. It’s located on the second storey and you have your own private entrance to the apartment. Linens are provided and the kitchen is fully stocked for cooking.
There is a laundromat available on site. We suggest taking a 10-minute walk to Sundowners, a steak house by the bay. John Pennekamp Coral Reef State Park is a mere 4-minute drive away.
Key Largo, Florida, United StatesAccommodates: 2
Top guest reviews
Host:
the hosts were very helpfulfriendly people and has a great home feelresponsive and accommodating hostsdownstairs renters had a party and they invited us to join they were very friendly and funwe arrived late at night but gino was kind enough to give us an extra hourLocation:
great little place in the middle of an rv parkit’s walking and biking distance to everything you need or want to do very safe areait is a nice place at a fantastic locationgreat location to do what you want in key largo or any of the upper keyswe last minute booked a 5 night trip and we were so lucky to get this placeCleanliness:
place was very clean and niceit was clean and well decoratedit was clean and bright with windows on all sides looking over the baythe place was lovely super clean and cozysetting is a nice clean well-run rv campground right on the waterRead more reviewsAmenities & Room:
the view from the room upstairs was beautifulbeautiful view of the sunset from the whole apartmentview is better than some beaches around the apartmentthe place is nice to stay clean great views and comfortablethe apartment is on the top floor with two efficiencies belowMonthly discount: 68% off
4. Two-bedroom house at Anglers Park, Key Largo (from USD 282)
Best for: Group stays
Anglers Park is part of Upper Florida Keys on Key Largo. There are two bedrooms in this accommodation, with two queen-size beds. There is central air conditioning in the apartment and linens are provided during your stay. You can prepare your meals at the fully equipped kitchen with a refrigerator and microwave.
Coin laundry is available on site. Do note that this house is not suitable for children and infants. There is also a late check-in time at 4 pm and an early check-out time at 10 am.
Key Largo, Florida, United StatesAccommodates: 4
Top guest reviews
Host:
super quiet community with helpful office staffgreat location within key largo staff was very welcoming and kindLocation:
excellent location for our short stayquiet friendly people all around you located near all the local marinasthis was a great place for our key largo fishing tripCleanliness:
place was great very clean spacious and quiet areaRead more reviewsAmenities & Room:
gino’s place was great spacious kitchen with a beautiful deck facing the beachplace is very spacious and great to hangout in dinning room and common areanice place with lots of room everything you need and moreMonthly discount: 67% off
5. Clean and tidy home near Florida Keys Aquarium Encounters, Marathon (from USD 1405)
Best for: Families with infants, group trips
Recent guests have given the feedback that this property was sparkling clean during their stay. You will be situated in Marathon, very close to the Florida Keys Aquarium Encounters. There are three bedrooms, and two and a half bathrooms.
Enjoy a private hot tub and outdoor grill after a long day of boating or day by the beach. There’s also plenty of parking space for your boat trailer. Towels and linens are provided. Curly’s Coffee and Marina is a short walk away, for your daily coffee fix.
Marathon, Florida, United StatesAccommodates: 8
Top guest reviews
Host:
host is very helpful and prompt with replies when neededshe was immediately responsive to any of our needs which were really very littleLocation:
cute house comfortable convenient locationthe location was great within walking distance of many activities marathon has to offergreat location and very reasonably priced for the location and quality of the rentalcecillia’s place was ideal for our time in the keysa fun aquarium fish market/restaurant bike rentals and snorkeling/diving company are all within walking distanceCleanliness:
house was clean bright decorated wellsuper clean and very friendly ownersuch a cute and clean housethe home was very clean with brand new kitchen appliancesthe neighborhood is calm and cleanRead more reviewsAmenities & Room:
fully stocked kitchen was great and the beds were very comfortablei wished we had been staying here for the entire winter - it was that comfortableMonthly discount: 30% off
6. Pet-friendly house near Rowell's Waterfront Park, Key Largo (from USD 3674)
Best for: Pet parents
This house fits five people comfortably and the host allows pets during your stay. You have access to the whole house, including the kitchen equipped with a refrigerator, oven, and microwave. There’s also an indoor washer and dryer for your laundry needs.
An outdoor storage shed can be a suitable place to store your bikes and kayaks. There are two bedrooms, with three beds and one bathroom. Check-in is available only after 4 pm.
Key Largo, Florida, United StatesAccommodates: 4
Top guest reviews
Host:
they were very helpful and answered all of my questions really fastvivian was the most friendly and helpful hostthey were friendly available and timelyhosts were very responsive and willing to help in any wayloved everything about this house and our experience with the hostLocation:
extremely quiet and beautiful getaway in the middle of key largoRead more reviewsCleanliness:
clean spacious nicely decorated homeeverything was clean and the house had everything you needed as wellwhen we arrived the house was very charming and cleanthank you so much for everything the place was clean and beautifulit was very comfortable and clean and the location was greatMonthly discount: 15% off
7. Spacious condominium near Kawama Yacht Club, Key Largo (from USD 1581)
Best for: Families with infants and kids
This spacious condominium is located in Key Largo near the Kawama Yacht Club. There are two bedrooms and two bathrooms in the accommodation. The master bedroom comes with a king-size bed and a sofa bed, while the other room has a queen-size and a double bed. It fits up to six guests comfortably.
You can use the shared amenities, including the two pools, a saltwater swimming lagoon, barbecue facilities, tennis courts, and playground.
Key Largo, Florida, United StatesAccommodates: 6
Top guest reviews
Host:
the host was very responsive and accommodatingLocation:
great location in key largothere is grocery shopping and multiple excellent restaurants very close to the condothe location was convenient though it would've been nice to be closer to a large beachthis is the most beautiful home to take a vacation and location to relax patricia keeps her home immaculatethanks for the laundry and dish soap very spacious and conveniently located close to nice restaurants and sightsCleanliness:
very clean and extemely comfortablethe condo was very clean and so so cutethe condo was spacious and extremely clean with various nice touches to make it extra welcoming and comfortablewell equipped and clean fourth floor condo in a great lkey largo locationRead more reviewsAmenities & Room:
the space is clean and well stocked with necessary tools and kitchen implementswe had 5 guests and the large living space and kitchen were perfectMonthly discount: 20% off
8. One-bedroom oceanfront apartment near Tavernier Creek Marina, Islamorada (from USD 1427)
Best for: Couples
This one-bedroom apartment is located on the sixth floor. It is a short drive away to Tavernier Creek Marina. The condominium is equipped with a full kitchen, modern appliances, and all the cookware you need to whip up a fulfilling meal. Enjoy your morning coffee on the balcony, while awaiting the stunning sunrise to start the day right.
Feel free to use the shared heated swimming pool at the complex. Coin laundry is available on site. Do note that the host’s place is unsuitable for children under 12 years old.
Islamorada, Florida, United StatesAccommodates: 2
Top guest reviews
Host:
everything else is provided by this great hosttad is a great hostvery responsive friendly ownertad is an outstanding hosttad was a great host before we even arrivedLocation:
very comfortable and close to many local attractionsclose to so many restaurants and attractionsplace is great for two people and close to everythinggreat location and just as advertisedtad's place is amazing located is just right in-between key largo and islamoradaCleanliness:
this place was clean and very spaciousthe apartment was clean and the bed very comfortablethe place was clean and quiet very niceclean and proximate to activities while also quiet in the eveningsthe place was very clean and comfortable defiantly would stay there againRead more reviewsAmenities & Room:
such a beautiful view and comfortable spaceit was very comfortable to sit out on the deck in the morning and have coffeethe heated pool was very nicealso shower gel and shampoo in the bathroom were very nicethe pool and beach are nice amenities although we didn't spend much time thereMonthly discount: 20% off
9. Modern unit with a large deck, Key West (from USD 265)
Best for: Beach lovers, watersports enthusiasts
Make yourself at home in this private end unit which includes all-new conveniences for a hassle-free experience. This property requires a minimum of seven nights of stay and offers a huge discount. After a long day of traveling, the bed and sofa bed will allow you to sleep peacefully.
The central air conditioning will keep you comfortable here during hot days, but you can cool down by swimming. The communal outdoor pool area is available from 6am to 8pm. You will also be given beach necessities such as snorkeling equipment to help you spend your day at the nearby beach.
Key West, Florida, United StatesAccommodates: 3
Top guest reviews
Host:
a wonderful place and a wonderful hostkristina is a wonderful host and i can't wait to returnchristina was an excellent host when any questions came up her communication back was asapLocation:
this condo is located in great locationsuper close to the best beachcondo was close to the best restaurants all within walking distancelocation amazing we enjoyed the bikes pool and of course the locationa great stay at a great locationCleanliness:
we loved staying at this condo very clean and comfortableRead more reviewsAmenities & Room:
great apartment in perfect location -- only two blocks off duval street in a quiet tree-lined neighborhoodthe bedroom was a great size very comfortable bed and such cute decor (and had a small tv)enjoyed the large patio and short walk to the poolthe house was so comfortable we had everything we neededthe bed is soft and comfy with two serra perfect sleeper pillows
10. A renovated home with luxurious amenities, Marathon (from USD 1725)
Best for: Group trips, budget travelers
Located in Marathon, close to several attractions, this property makes an excellent home away from home. It has been refurbished to a high degree and has upscale facilities for a seamless stay. The sufficient lighting and smooth white walls, creating a pleasant and airy space add a luxurious touch to the vacation. For convenient meal preparation, the kitchen has stainless appliances ready to fulfill your culinary desires.
Furthermore, board games, WiFi, and HDTV are available for some indoor entertainment. The private backyard includes a barbecue grill and a picnic table for your exclusive use. A three-night minimum stay is necessary, and you will receive big weekly discounts too.
Marathon, Florida, United StatesAccommodates: 6
Top guest reviews
Host:
owner was responsive and very helpfuleven pet friendly if you neededdefinitely the more luxurious among what is available in marathon:) host yery was very nice and helpfulvery cute place very nice hostLocation:
great place and convenient locationgreat house in a great locationclose to most beaches and attractionsgreat location in the middle keysthe location was central and was in a quiet safe areaCleanliness:
great place very clean and comfythe house was clean and comfortablethe house was very clean and in a safe areathe place was clean nicely decorated and well organizedyery's place was clean and check-in was easyRead more reviewsAmenities & Room:
the space was clean and the air conditioner worked very wellthe backyard was pleasant to sit and read or eat at the picnic tablethe home smelled amazing the shower and bathroom amenities were great
11. Islamorada Haven, Tavernier (from USD 150)
Best for: Pet parents, outdoor enthusiasts
Newly renovated and designed with guests’ comfort in mind, this home by a canal has everything you’ll need for your relaxing summer vacation. The rental can accommodate six guests as well as up to four dogs. A boat ramp is also available here, which is great news for those who want to kayak and paddleboard. Guests will have access to the property’s tandem kayak.
You can enjoy a peaceful afternoon with the kids in Theater of the Sea or learn something new at the Windley Key Fossil Reef Geological Park, both of which are located in the area.
12. Beachfront Ocean Duplex, Long Key (from USD 900)
Best for: Beach lovers, group stays
A group of 10 can reside in this home comfortably since there’s plenty of space in this rental. One dog is welcome here too! You can take a peaceful walk on the secluded beach and listen to the relaxing sound of the waves crashing into the shore. Guests can choose to rent the entire duplex or separate units.
Fun and vibrant decorations can be found all over the house. Everyone can gather around in the living room and enjoy a movie on the wide flat-screen TV. Most of the rooms in this rental provide amazing views of the ocean.
13. Fisherman's Retreat, Conch Key (from USD 188)
Best for: Group stays
Situated right in the fishing community of Conch Key, this rental’s bright and airy atmosphere is sure to provide you with the best fishing trip experience. The rental offers beautiful views of the ocean, and a dock can be found at the back. You can rent a boat or jet ski nearby. Fishing bait can be stored in the freezer provided on the premises.
Up to eight guests can stay in this spacious retreat. Two connected studio apartments are available for rent, and you’ll have the option of renting both or just one if you’re traveling with a smaller group.
14. Marathon Waterfront Recreational Paradise, Marathon (from USD 400)
Best for: Outdoor enthusiasts, group stays
This four-bedroom home is located next to the bay and is the perfect summer getaway. This spot is a great choice if you want to fish, explore the area, or just relax. If you feel like going for a swim, you’ll have a lot of options. Guests will have access to a swimming pool and a private beach.
A blue and white color scheme is employed throughout the home, matching the tropical atmosphere of the area. Spectacular ocean views can be viewed from the numerous large windows.
15. Key Lime Calypso, Key West (from USD 202)
Best for: Group stays
This rental has a well-equipped kitchen, a private laundry area, and a cable TV. You can light up the grill on the patio for a fun cookout or relax in the heated pool and feel all your worries fade away.
The cottage is located in Old Town, so guests can conveniently check out the popular attractions of Key West. You can conveniently take a family picnic in Nancy Forrester’s Secret Garden, have a peaceful walk on Dog Beach, and take a look at some fascinating exhibits in nearby museums while staying here.
16. Cottage with a balcony and back porch, Marathon (from USD 494)
Best for: Outdoor enthusiasts, group stays
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 homey 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.
Marathon, Florida, United StatesAccommodates: 8
Top guest reviews
Host:
love this place adorable comfortable friendly hostsbarry jim and pam are the most thoughtful and kind hosts i have ever encounteredRead more reviewsAmenities & Room:
terrific location beds were comfy and the small island vibe is terrific
17. Charming oceanfront cottage for six, Cudjoe Key (from USD 2037)
Best for: Beach lovers, watersports enthusiasts
Featuring ocean-themed décor and aqua tones, this homey 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.
Cudjoe Key, Florida, United StatesAccommodates: 6
Top guest reviews
Host:
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 recommendLocation:
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 boardingCleanliness:
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 forRead more reviewsAmenities & Room:
fantastic views beautiful kitchen and comfortable bedsbeautiful view nice pool and swimming areacommunity pool was great and looked like it was recently re done
18. Tidewater Views, Cudjoe Key (from USD 1384)
Best for: Group trips, outdoor enthusiasts
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.
Cudjoe Key, Florida, United StatesAccommodates: 6
Top guest reviews
Host:
space had everything that was advertised and the property manager was very responsive and welcomingLocation:
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 getawayCleanliness:
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 arrivedRead more reviewsAmenities & 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 gift
19. Sea Glass Cottage, Tavernier (from USD 12609)
Best for: Watersports enthusiasts, group stays
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.
Tavernier, Florida, United StatesAccommodates: 6
Top guest reviews
Host:
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 emailsLocation:
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 hesitationCleanliness:
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 hostRead more reviewsAmenities & 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 room
20. Captivating houseboat, Key Largo (from USD 175)
Best for: Outdoor enthusiasts
Enjoy the waters of the Florida Keys by staying on top of it. This houseboat rental in Key West provides a unique boat ride experience with the comforts of a typical home. Besides a bedroom, a bathroom, a kitchen, and a living area, this houseboat also has two upper decks so you can enjoy your coffee time or alone time under the sun, or take in the stunning views at sunset with wine or cocktails.
The property also has kayaks and paddle boards to enjoy the water, plus there is quick access to the beach. Bring your furry pets along, subject to pet fees depending on the dog breed.
Key Largo, Florida, United StatesTop guest reviews
Host:
abigail is a great hostabigail was an awesome hostabigail was the best host we have ever hadthe owners of the surrounding boats are so friendlyvisitors can expect a friendly host who responds in a timely manner and provides useful advice to her clientsLocation:
amazing location and wonderful placethe location is wonderful secluded yet everything you need is close bylocation was great - near many bars and restaurants which were walkablethe location is amazing 100% worth itthanks great experience and locationCleanliness:
the boat was very clean the towels smelled fresh and clean as did the sheetseverything was clean and in good working orderthey kept it very cleanthe shower house/bathrooms are kept extremely clean as wellwe absolutely had everything we needed and the bathhouse was very clean and convenientRead more reviewsAmenities & Room:
comfortable couch and bed and cool sleeping space for kids under the helmhe loved it and there was a fan to help with air circulationyet has excellent wifi/cell service for work/communicationbed was comfy and the big couch is awesomethe houseboat was very comfortable for us
21. Unique yacht, Key West (from USD 148)
Best for: Beach lovers, outdoor enthusiasts
If you want to have a different kind of trip, the Serenity yacht is the perfect vacation rental for you. It has got all the essentials of a home, with two beds that can sleep two people each, a bathroom, a mini kitchen, a dining/living area, and a private covered patio on the boat. The boat is docked next to Blackwater Siren, a quiet tiki bar, plus a bait shop where you can rent jet skis and pontoons.
There is also a private area on the deck with chairs and tables plus a gas and charcoal grill for your use. If you’re a beach enthusiast, the nearest stretch of sand and coast is only within a short walking distance.
Key Largo, Florida, United StatesTop guest reviews
Host:
david was a great hostthe hosts were awesomeolivia and will were great hostsour host was so kind and attentive to our every needthe owner very responsive and helpful check in and out went smoothlyLocation:
great location off the beaten pathgreat location with everything you need right thereamazing time the location was perfectgreat location on a quiet shorelinegreat location-excellent food and drinks at the blackwater sirenCleanliness:
very clean and stocked with everything you needwe found it to be clean and preparednice and clean accommodation special place to spend the nightthe cleanliness of the main outside cabin is an issue with the inside being generally cleanthe place was clean quiet and just a fantastic place to relaxRead more reviewsAmenities & Room:
ice cold ac and nice not water for showerthe bed was very comfortable and the ac worked greatthe inner cabin was flawless and beds were very comfynice having breakfast on the “porch” back end of the boat with the water viewsthe bed super comfy
22. Lovely rental, Key Largo
Best for: Outdoor enthusiasts, group trips
This two-bedroom vacation home in Key Largo is creatively designed with tropical colors to give you the feel of the ocean even while inside the house. For its affordable nightly price, it has all your basic needs covered. Enjoy your breakfast on the breakfast bar by the kitchen or out on the patio. Relax on the plush couch in the living room and watch a movie on DVD or cable on the flatscreen TV.
Additionally, you can enjoy the days swimming in the ocean or the pool, or play a match at the tennis courts. And if you want to go downtown, it’s just a few minutes away on foot.
98422 Windward Ave.
23. Beach cottage, Cudjoe Key
Best for: Watersports enthusiasts
The Sea Breeze Cottage is inside a gated community to give you security and privacy during your stay. This cozy cottage has recently been updated with new Smart TVs in the living room and bedrooms, an expanded cable TV, and high-speed WiFi. Enjoy the double kayak provided by the owners or enjoy a picnic under the sun at the nearby state parks using the coolers and beach towels they’ve also provided.
There are no private docks for your boat, but there is an overflow lot nearby where you can park your boat.
Top guest reviews
Host:
any problems were dealt with a sense of urgencyIf I could have changed anything it would have been the oven Even with written instructions we could not get the oven to bakeSandy always answered the phone when we had a questionOnly problem was our check inThe cabin was chock full of helpful hints of things to doLocation:
: House is located about 1 mile from the Square Grouper arguably the best seafood place in the KeysNice place with a great locationExcellent location close to KWwhich was a bummer but all in allit was a great trip and Sandy was very helpful in setting everything upCleanliness:
Property in in tip-top condition; super cleanVery clean cozy 2 bedroom 2 bathThe cottage had everything we needed was clean and comfortableRead more reviewsAmenities & Room:
and right on the water with marina accessIt made it feel cozy and invitingOnly room for parking one vehicle at the Cottage Second car had to be parked in overflow by midnight each nightIf you are looking for a great time and a cozy house with everything you need this is the one for youThe weather from the storm kept the temps low and comfortable
24. Sun, Sea and Sky, Key West
Best for: Families with kids, group stays
Experience leisure at its finest in this fully air-conditioned condo near Truman Water Park. The compact space at this holiday rental in the Florida Keys is thoughtfully adorned with stylish decor, maximizing both aesthetics and functionality. Sink into the plush comfort of the living room’s sofas, creating a haven of relaxation. Stay connected with WiFi access, and indulge in entertainment with three TVs - one in each room, promising versatile viewing options.
Discover culinary possibilities in the well-equipped kitchen complete with a foldable dining table for intimate meals. The convenience of a walk-in closet enhances your stay, ensuring an organized space. For leisure and relaxation, the communal pool awaits just outside the condo, accompanied by a lounging area that invites you to bask in the sun’s warmth.
Key West, Florida, United States
25. Exclusive tropical oasis with heated pool, Key Colony Beach
Best for: Beach lovers, families with kids
This tropical condo in Key Colony Beach is situated on a private beach for families to enjoy. It’s got two bedrooms which can accommodate four people, with flatscreen TVs in every bedroom, plus another flatscreen TV in the living room. The beachfront rental also has a heated swimming pool, shuffleboard, and tiki huts. You’ll surely enjoy amazing ocean views throughout your stay.
Countless activities await you at the sea when you decide to rent kayaks, jet skis, and snorkels from the many charters nearby. If you want to explore other popular beaches in the area, you can bask under the sun at Sombrero Beach or Coco Plum Beach.
Key Colony Beach, Florida, United States
Top guest reviews
Host:
Wow Great vacation Absolutely beautiful areaMichael provided information about what to do entertainment and attractionsBeach area is very well maintained as wellGreat property central to everythingThe condo was clean and the grounds very well kept Michael was great to communicate offered suggestions on things to do and places to eat Appreciated that the condo was well stocked with things ...Location:
It was great location Easy to get everywherebest of all Key Colony Beach is just lovely in every wayThe condo was spacious in immaculate shape and at a great location Beach just steps away with a great pool even closerThe location to the pool and beach is perfectwalking distance from restruants Marinas and shops and sunset beachRead more reviewsAmenities & Room:
The condo was everything that was advertisedand you had everything you needed right thereThe condo was exactly as described but even betterPlace was great where we stayed and would do it all over againnever mind looking out the window at the pool
26. Home leading to the Atlantic Ocean, Summerland Key
Best for: Group stays, families
One of the beach house rentals in Summerland, an island found in the lower Florida Keys, this home will have you spoiled with ocean views. It overlooks the canal with boat slips that have easy access to the Atlantic Ocean. With brand-new kitchen appliances and living room furniture, it’s a great vacation rental in Key West, Florida to be enjoyed with family.
You can rent kayaks in nearby rental shops to explore the ocean or you can bring fishing gear and cast your rod on the nearby boat dock.
Summerland Key, Florida, United States
Top guest reviews
Host:
owner seems like a very pleasant personWonderful property - communication with the owner was amazing and we would definitely stay here againFishing was some of the best we have experienced House was clean and very niceAnd there was great kayaking alsoThe location was great for usLocation:
The canal is quiet and perfect for paddle boardingThe location was perfect for getting out fishing into either the Atlantic or the Gulf-weather dependingRead more reviewsAmenities & Room:
It is a short channel ride to the AtlanticThe screened in deck was awesomeThere is a nice little coffee/ ice cream shop 1 mile up the road that we would ride the bikes toIt suited our needs perfectly from the Goliath Grouper in the canal to the comfortable beds & furniture & all in betweenThe house was very comfortable
27. Bright home in Old Town, Key West
Best for: Outdoor enthusiasts, couples
Stay in this beautifully landscaped and newly renovated vacation rental in Old Key West, near Smathers Beach. It’s got a fully furnished kitchen and a bedroom with a queen-size bed, and a living room with TV and high-speed WiFi. French doors open up to a balcony with chaise lounges where you can enjoy the canopy of palm trees and sip your favorite drink at sunset.
The charming beach condo is located at the entrance of Ft. Zachary Taylor State Park and Beach, and two blocks away from the lively Duval Street. There are two bikes provided that you can use during your stay. This rental house in Key West comes with a pool offering an ideal escape for couples vacationing in Florida.
Key West, Florida, United States
Top guest reviews
Host:
Place was decorated very well and furnished with newer furniture European appliances Have already scheduled for next yearso I was excited to see what she had done with this new oneAnd she's raised the bar againand I am hoping this Condo is available when I do soThe room was comfortable upgraded and was very nicely decorated The owner communicated with us very well before and during our stay and left us contact numbers in case we had any concerns while w...Location:
Everything has been thought out from WiFi and USB plugsIt was in a great location just a short walk to duvalThis was by far one our best stays in Key WestIt's perfectly positioned just 5 mins to Fort Zac or the Green ParrotTwo great bicycles are available to get around townCleanliness:
The condo was lovely - beautifully decoratedVery clean and in a great spot close to everything on DuvallThe location was perfect and the property was clean and well maintainedRead more reviewsAmenities & Room:
all the kitchen gear you might need super comfy bed - and an ideal locationhad everything we could have wanted - beach chairs beach towelsthis home has everything you need A second story one bedroom with a full kitchen and deckIt had everything that you would need to make your stay comfortableThe condo is decorated beautifully and has all the little amenities you will need Great people to deal with also
28. Elegant condo at Ocean Pointe Suites, Tavernier
Best for: Group stays, beach lovers
Enjoy the comfort and security of a gated resort community at this exquisite condo, offering vistas of treetops and the ocean. This beachfront Vrbo in Florida features a well-equipped kitchen and a foldable dining table, making meals a delightful experience. The well-ventilated and naturally lit living room invites you to unwind, complete with a TV for entertainment and WiFi access.
Outside, the communal pool beckons, complemented by a hot tub, ensuring leisure and fun for all. Resort living extends to the beach, where kayaks and paddleboards await your aquatic adventures. A cafe and bar within the resort promise daily breakfast delights. Fitness enthusiasts will appreciate access to the shared gym and sports center.
Tavernier, Florida, United States
29. Comfortable studio unit with a shared marina, Marathon
Best for: Outdoor enthusiasts, couples
When you book this studio unit set in a private neighborhood, you will have an utterly pleasant trip to Florida Keys. To make you feel more at home, it has a small kitchen with a refrigerator, stove, dinnerware, and a dining table for two. You may also use the gas barbecue to enjoy alfresco meals on the picnic bench outdoors.
Furthermore, during happy hour, you may drop by the communal tiki hut and have a glass of wine. The property also offers access to a communal marina with a boat ramp that may be used for an additional cost. There is even a swimming pool available for your leisure. Also, if you’re planning to stay for seven nights or more, you will undoubtedly enjoy a substantial discount for your convenience.
Marathon, Florida, United States
30. A fully furnished duplex home with a large deck, Marathon
Best for: Beach lovers, watersports enthusiasts, families with kids
This duplex home on Long Key’s private beach is a great option for both adults and children. It is a great home away from home since it has cozy bedding and complete toiletries. The kitchen has a microwave, refrigerator, and pantry goods to assist you in preparing your favorite meals. Moreover, the huge deck is the property’s highlight since it boasts a tiki hut, perfect for viewing Atlantic Ocean. If you want to have some fun in the waters, you may utilize the kayaks or paddleboards provided.
Moreover, staying here will give you the ultimate convenience due to its excellent accommodation package. Additionally, you will be given a weekly discount for stays of at least seven nights here.
Layton, Florida, United States
31. Impeccable vacation home with a hot tub, Marathon
Best for: Group trips
When you book this vacation house for a short-term stay, you will receive a considerable weekly discount, making it ideal for budget-friendly travel. The facility has enough activities to keep you engaged throughout. From December to March, you can take advantage of the private heated pool. Besides that, the poolside tiki hut bar has an outdoor barbecue and an ice machine to help you make your favorite snacks and drinks.
This property also has a lit dock with underwater lighting for convenient night fishing. You may join a fishing charter excursion for a fee if you want to explore the region. Furthermore, adults can unwind in the brand-new hot tub after a long tiring day.
Key Colony Beach, Florida, United States
32. A two-bedroom unit with a flat-screen TV, Key West
Best for: Senior citizens, beach lovers
This rental lies on the third level of Sunrise Suites Resort but is accessible by an elevator. The property is also only a short walk from the beach, making it an ideal base for your oceanfront vacation. Aside from these benefits, you will receive a large discount on your rental fee even if you stay for around seven nights!
Other than that, your room has a comfortable living space with a flat-screen TV where you can watch your favorite shows. You may also relax in the onsite pool and hot tub while staying at the resort. There’s also a communal picnic area where you may socialize with other guests. Additionally, you are welcome to utilize the gym if you want to maintain your fitness routine. Concierge service is also available here to meet all your requirements.
Key West, Florida, United States
Top guest reviews
Read more reviewsCleanliness:
condo complex was old but clean and comfortablewe stayed there for 3 nights and the property was clean quite and everything workedit could use some updating but it was cleanthe condo was clean and charming however a ways away from duval street and other attractions
33. Beautiful rental property with ocean views, Cudjoe Key
Best for: Group stays
Wake up to breathtaking ocean views every morning when you book this property in Cudjoe Key. It reflects the relaxed but enjoyable ambiance of the beach with its bright furnishings. Moreover, it has five bedrooms, each with plush linens and a TV. Air conditioning and heating are also available to assure your utmost comfort in any weather.
While staying here, visit the pool area to swim or simply relax on the loungers. This property also has a private dock for kayaking and paddling. Furthermore, if you plan to stay here for seven nights or more, you will receive a discount.
Summerland, Florida, United States
34. Exclusive property with a private pool, Marathon
Best for: Watersports enthusiasts
Enhance your Florida Keys vacation by reserving this private home, offering everything you need to feel at ease here. The private pool area, where you may swim or rest on the sun loungers, is one of its highlights. There’s also an outdoor patio which is the perfect spot to hang out with your companions.
Moreover, the open-plan living room with a kitchen and dining area has a cozy ambiance. You can also make something delicious for your loved ones using the microwave, oven, and stove offered. If you want to spend the day outdoors, you may rent paddle boards and kayaks from the property itself. In addition to these benefits, reserving this property will provide you with a substantial discount.
Marathon, Florida, United States
Top guest reviews
Location:
this house is so cute and is in an excellent locationgreat place to walk and run in the areaCleanliness:
the home was clean and well cared forRead more reviewsAmenities & Room:
the beds were so comfortable
35. Spacious beachfront home, Key Largo
Best for: Families with kids, group trips
This home is situated on the beachfront, with towering trees in the surrounding area to help you relax. After a long day, you may relax in the heated pool or hot tub. Besides that, if you want to have some outdoor water fun, you may rent kayaks and a boat on-site.
Additionally, cable TV and toys are provided to keep children entertained if they want to stay indoors. Furthermore, this property has a four-night minimum stay requirement, and if you stay for a week or longer, you will receive a considerable discount on your rental.
Key Largo, Florida, United States
Top guest reviews
Location:
great location that feels very privateoverall a great trip at a great house in an exceptional location on the watergreat house in an amazing location that was even better than advertisedRead more reviewsAmenities & Room:
the beds were incredibly comfortable the outside with the pool dock beach paddle boards etc
36. Cozy cottage with a private dock, Islamorada
Best for: Watersports enthusiasts, families, group trips
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.
Islamorada, Florida, United States
Top guest reviews
Host:
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 rampLocation:
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 PabloCleanliness:
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 aboutRead more reviewsAmenities & 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 paradise
37. Waterfront cottage with a large deck, Marathon
Best for: Group trips
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.
Marathon, Florida, United States
Top guest reviews
Host:
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 longerLocation:
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 placesCleanliness:
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 stockedRead more reviewsAmenities & 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 comfortable
38. Spacious cottage with harbor views, Marathon
Best for: Group stays
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.
Duck Key, Florida, United States
Top guest reviews
Host:
the owner was very responsiveproperty owner was easy to work withvery good communication from the owner and very easy to work withCleanliness:
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 reviewsAmenities & 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 needed
39. Waterfront home close to the beach and pool, Key Colony Beach
Best for: Group trips
Casa Mar Azul 2 is a vacation rental in the heart of the Florida Keys. This accommodation option has an open-plan kitchen/living area with a flat-screen TV and a sliding door that leads to a covered patio. If you want to experience the beach, a private pool, and drink at a pool bar, and eat at nearby casual dining options, head on to the Cabana Beach Club. Renting the house entitles you to free passes to the Beach Club.
Moreover, there is a nearby golf course, a children’s playground, tennis courts, boat rentals, basketball courts, and Sunset Park. For more outdoor thrills such as hiking, kayaking, and fishing, you can take a quick drive to Curry Hammock State Park.
Top guest reviews
Host:
love the kcb areawonderful experiencethe canal front was wonderful and was nice to walk along in the eveningswe have been coming to the florida keys for a very long time and i can say that casa mar azul ii is one of the very best places we have every stayedhaving a dock made us able to rent a boat for three days which we had the perfect weather for and we caught a lot of different kinds of fish! everything at the rental was clean - the only problem w...Location:
great locationthe location is amazing and we enjoyed the pool and beach at the cabana clubnice canal locationchecking in and out was a breezegreat location for people with a boatCleanliness:
property was as described and very cleanthis place was very nice and clean, and updated throughoutother than that, the house was clean, comfortable and exactly what we saw onlinenicely decorated, great location, boat dock was perfectwhat cute place this was, very clean and everything needed for a perfect vacationRead more reviewsAmenities & Room:
the kitchen was well equipped for what we needed and the master bed was very comfywe loved the place, kitchen was fully stocked with everything you need, plenty of towels, and extra sheets for the sofa bedthe only thing i would say to add would be a hook for the towels in the bathroom in the hallwaywe enjoyed the pool at the cabana club when we were not utilizing the dock for paddleboarding & kayakinghad everything we needed
Enjoy the vibes of Key West, Florida
Enjoy the breezy and warm weather, pristine beaches, and international culture without leaving the country when you book a home from this selection of vacation rentals in Florida Keys, USA. On your trip, feel free to fill your days with activities and take pleasure in the island life under the sun, underwater, or on top of the white sands. You’re guaranteed to feel recharged at the end of your beach trip in this beloved vacation destination.
Frequently asked questions about the top vacation rentals in Florida Keys, USA
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