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. 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.
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 April 07, 2024.
1. Sun, Sea and Sky (from USD 264)
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.
2. Elegant condo at Ocean Pointe Suites (from USD 275)
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.
3. Private mini resort in Key West (from USD 1970)
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.
Top guest reviews
Amenities & Room:
the house was very comfortable and had everything we needed and moreHost:
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 helpfulRead more reviewsLocation:
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 group
Superhost
4. Exclusive tropical oasis with heated pool (from USD 342)
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.
Top guest reviews
Amenities & 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 poolHost:
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 ...Read more reviewsLocation:
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 beach
5. Summerland home leading to the Atlantic Ocean (from USD 189)
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 is overlooking 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.
Top guest reviews
Amenities & 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 comfortableHost:
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 usRead more reviewsLocation:
The canal is quiet and perfect for paddle boardingThe location was perfect for getting out fishing into either the Atlantic or the Gulf-weather depending
6. Bright home in Old Town, Key West (from USD 230)
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.
Top guest reviews
Amenities & 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 alsoCleanliness:
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 maintainedHost:
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...Read more reviewsLocation:
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 town
7. Treetop loft in Key Largo (from USD 176)
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.
Top guest reviews
Amenities & 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 bathroomCleanliness:
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 cleanHost:
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 beautifulRead more reviewsLocation:
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 water
8. Captivating houseboat in Key Largo
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
Amenities & 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 usCleanliness:
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 convenientHost:
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 clientsRead more reviewsLocation:
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 location
9. Unique water experience in Key West
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
Amenities & 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 comfyCleanliness:
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 relaxHost:
the hosts were awesomedavid was a great hostolivia 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 smoothlyRead more reviewsLocation:
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 siren
Enjoy the oceans 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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