Top 10 Vacation Rentals In Florida Keys, USA - Updated 2021

vacation rentals in florida keys
Jaclyn
Jaclyn
Updated

Florida Keys is at the southernmost part of the US, a place so different from the nightlife of Miami and the theme park adventures of Orlando. Come to this part of Florida to experience a true escape from the city. Key West is about 4 miles (6.4 km) long and famous for its watersports, beaches, lively nightlife, and conch-style buildings and houses. Best time to visit Key West is during winter or spring when it’s not raining during the hurricane season. Check out these top 10 vacation rentals in Florida Keys, USA. Be sure to book early, especially if you’re going during a tourist season.

1. Private mini resort in Key West (from USD 2899)

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 here for everyone. Plus the house is located far away from downtown and the crowds but near enough that it’s still easy to access. It’s perfect for reunions, birthday trips, or big family/friends trips.

Real World MTV House Key West
57 reviews  Wifi Available
Entire residential home 12 Beds 16 Guests 10 Bedrooms 5 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
the house was very comfortable and had everything we needed and more
Host:
andrew is a great host and communicates everything to make sure expectations are aligned
the owner/host knows everyone in town so is able to help make your vacation dreams come true
aric the house manager was great to work with and very accommodating to our questions
the hosts were very communicative prompt and laid out all expectations easily for us
andrew and his grounds person were very welcoming and helpful
Location:
the neighborhood is beautiful quiet and fairly convenient to downtown key west
great location if your group wants to stay in a lot
great location great amenities great service
hopefully we can get back to this place sooner then later
it is the perfect place to celebrate with a big group
Read more reviews

2. Private tropical oasis with heated pool (from USD 201)

This tropical condo in Key West is situated on a private beach. 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 vacation rental also has a heated swimming pool, a shuffleboard and tiki huts. And it’s only five minutes’ away from places where you can rent kayaks, jet skis, and snorkels.

Private Tropical Beach-No Stairs-Great Location-Heated Pool-Wifi-It's LOADED!!!
71 reviews
condo 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The condo was everything that was advertised
and you had everything you needed right there
The condo was exactly as described but even better
Place was great where we stayed and would do it all over again
never mind looking out the window at the pool
Host:
Wow Great vacation Absolutely beautiful area
Michael provided information about what to do entertainment and attractions
Beach area is very well maintained as well
Great property central to everything
The 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 everywhere
best of all Key Colony Beach is just lovely in every way
The condo was spacious in immaculate shape and at a great location Beach just steps away with a great pool even closer
The location to the pool and beach is perfect
walking distance from restruants Marinas and shops and sunset beach
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3. Summerland home leading to the Atlantic Ocean (from USD 159)

This three-bedroom Summerland vacation rental overlooks the canal with easy boat 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 fish from your boat on the nearby dock.

LIVING IN BEAUTIFUL PARADISE
7 reviews
House 3 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
It is a short channel ride to the Atlantic
The screened in deck was awesome
There is a nice little coffee/ ice cream shop 1 mile up the road that we would ride the bikes to
It suited our needs perfectly from the Goliath Grouper in the canal to the comfortable beds & furniture & all in between
The house was very comfortable
Host:
owner seems like a very pleasant person
Wonderful property - communication with the owner was amazing and we would definitely stay here again
Fishing was some of the best we have experienced House was clean and very nice
And there was great kayaking also
The location was great for us
Location:
The canal is quiet and perfect for paddle boarding
The location was perfect for getting out fishing into either the Atlantic or the Gulf-weather depending
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4. Bright home in Old Town, Key West (from USD 175)

Stay in this beautifully landscaped and newly renovated vacation rental in Old Key West, Florida. It’s got a fully furnished kitchen and a bedroom and a living room with TV and high-speed WiFi. French doors open up to a balcony with chaise lounges where you can enjoy drinks at sunset. The condo is located at the entrance of Ft. Zachary Taylor State Park and Beach, and two blocks away from the lively Duval St. There are two bikes provided that you can use during your stay.

Upscale end unit home @ Truman Annex close to Duval St
31 reviews
condo 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
all the kitchen gear you might need super comfy bed - and an ideal location
had everything we could have wanted - beach chairs beach towels
this home has everything you need A second story one bedroom with a full kitchen and deck
It had everything that you would need to make your stay comfortable
The condo is decorated beautifully and has all the little amenities you will need Great people to deal with also
Cleanliness:
The condo was lovely - beautifully decorated
Very clean and in a great spot close to everything on Duvall
The location was perfect and the property was clean and well maintained
Host:
Place was decorated very well and furnished with newer furniture European appliances Have already scheduled for next year
so I was excited to see what she had done with this new one
And she's raised the bar again
and I am hoping this Condo is available when I do so
The 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 plugs
It was in a great location just a short walk to duval
This was by far one our best stays in Key West
It's perfectly positioned just 5 mins to Fort Zac or the Green Parrot
Two great bicycles are available to get around town
Read more reviews

5. Treetop loft in Key Largo (from USD 138)

Located inside a gated community, this treetop vacation rental in Key Largo, Florida lets you enjoy a simple vacation close to nature. The treetop apartment 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. You can also rent kayaks, paddle boards, and snorkels and use them within a specified area of the water for safety reasons.

Slep1-4 (22 steps)Beach 5 min paddle.5-Star(TT)
Key largo, Florida, United States
458 reviews  Wifi Available
Entire loft 3 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
it was spacious comfortable and had an incredible sitting space on the deck in the tree tops
tree tops apt is a great place if you are looking quiet and serenity
a very nice place at the sea where you can borrow kayaks and relax on sun beds
very spacious immaculate well furnished tree tops apartment nice outside space though maybe a little small
cozy bed and yes yummy pillows ;) fully equipped kitchen and everything you need in the bathroom
Cleanliness:
our room was very clean
quick communication with host clean
the apartment was very neat clean private and peaceful
this could be a nice space if cleaned and fixed up
room was just as described and clean
Host:
the instructions and tips provided were very detailed and the owner had some nice recommendations for food
host is friendly and helpful
leslie was a wonderful host and responded quickly to questions
beautiful place and hosts kind and hospitable
the owner had christmas decorations during this time making place look all the more beautiful
Location:
the location was great very close to the water
this is a lovely location
really nice location for swimming and enjoying the sunset
great location and best value on key largo
great location and beautiful property on the water
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6. Waterfront home close to the beach and pool

Casa Mar Azul 2 is a vacation rental in the heart of the Florida Keys. This two-bedroom house has an open plan kitchen/living area with a flatscreen TV and a sliding door that leads to a covered patio. If you want to experience the beach, a swimming pool, and drink at a pool bar, and eat at nearby restaurants, head on to the Cabana Beach Club. Renting the house entitles you to free passes to the Beach Club. There is also a nearby golf course, a children’s playground, tennis courts, boat rentals, basketball courts, and the Sunset Park.

WATERFRONT, WALK TO CABANA BEACH CLUB, DOCK, GOLF * SALE* 4/17-5/21 $952WK
47 reviews
House 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
the kitchen was well equipped for what we needed and the master bed was very comfy
we loved the place, kitchen was fully stocked with everything you need, plenty of towels, and extra sheets for the sofa bed
the only thing i would say to add would be a hook for the towels in the bathroom in the hallway
we enjoyed the pool at the cabana club when we were not utilizing the dock for paddleboarding & kayaking
had everything we needed
Cleanliness:
property was as described and very clean
this place was very nice and clean, and updated throughout
other than that, the house was clean, comfortable and exactly what we saw online
nicely decorated, great location, boat dock was perfect
what cute place this was, very clean and everything needed for a perfect vacation
Host:
love the kcb area
wonderful experience
the canal front was wonderful and was nice to walk along in the evenings
we 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 stayed
having 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 location
the location is amazing and we enjoyed the pool and beach at the cabana club
nice canal location
checking in and out was a breeze
great location for people with a boat
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7. Captivating houseboat in Key Largo

Enjoy the waters of the Florida Keys by staying on top of it. This houseboat rental in Key West gives you the comforts of home while literally living on top of the ocean. 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 views at sunset with wine or cocktails. They have 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.

houseboat in paradise with beach
Key Largo, Florida, United States
245 reviews
Boat 3 Beds 1 Bedroom
Top guest reviews
Amenities & Room:
comfortable couch and bed and cool sleeping space for kids under the helm
he loved it and there was a fan to help with air circulation
yet has excellent wifi/cell service for work/communication
bed was comfy and the big couch is awesome
the houseboat was very comfortable for us
Cleanliness:
the boat was very clean the towels smelled fresh and clean as did the sheets
everything was clean and in good working order
they kept it very clean
the shower house/bathrooms are kept extremely clean as well
we absolutely had everything we needed and the bathhouse was very clean and convenient
Host:
abigail is a great host
abigail was an awesome host
abigail was the best host we have ever had
the owners of the surrounding boats are so friendly
visitors can expect a friendly host who responds in a timely manner and provides useful advice to her clients
Location:
amazing location and wonderful place
the location is wonderful secluded yet everything you need is close by
location was great - near many bars and restaurants which were walkable
the location is amazing 100% worth it
thanks great experience and location
Read more reviews

8. Live like a local at this beach cottage

The Sea Breeze Cottage is inside a gated community to give you security and privacy during your stay. This two-bedroom 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.

Live Like a Local in our Venture Out Florida Keys Fully Equipped 2B/2Ba
53 reviews
cottage 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
and right on the water with marina access
It made it feel cozy and inviting
Only room for parking one vehicle at the Cottage Second car had to be parked in overflow by midnight each night
If you are looking for a great time and a cozy house with everything you need this is the one for you
The weather from the storm kept the temps low and comfortable
Cleanliness:
Property in in tip-top condition; super clean
Very clean cozy 2 bedroom 2 bath
The cottage had everything we needed was clean and comfortable
Host:
any problems were dealt with a sense of urgency
If I could have changed anything it would have been the oven Even with written instructions we could not get the oven to bake
Sandy always answered the phone when we had a question
Only problem was our check in
The cabin was chock full of helpful hints of things to do
Location:
: House is located about 1 mile from the Square Grouper arguably the best seafood place in the Keys
Nice place with a great location
Excellent location close to KW
which was a bummer but all in all
it was a great trip and Sandy was very helpful in setting everything up
Read more reviews

9. Unique water experience in Key West

If you want to have a different kind of trip, book the Serenity yacht as a vacation rental in the Florida Keys. It’s 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. You’ll also be a short walk away from the nearest beach if you want to go swimming.

Yacht in Key Largo, Florida
Key Largo, Florida, United States
382 reviews
Boat 2 Beds 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
ice cold ac and nice not water for shower
the bed was very comfortable and the ac worked great
the inner cabin was flawless and beds were very comfy
nice having breakfast on the “porch” back end of the boat with the water views
the bed super comfy
Cleanliness:
very clean and stocked with everything you need
we found it to be clean and prepared
nice and clean accommodation special place to spend the night
the cleanliness of the main outside cabin is an issue with the inside being generally clean
the place was clean quiet and just a fantastic place to relax
Host:
the hosts were awesome
david was a great host
olivia and will were great hosts
our host was so kind and attentive to our every need
the owner very responsive and helpful check in and out went smoothly
Location:
great location off the beaten path
great location with everything you need right there
amazing time the location was perfect
great location on a quiet shoreline
great location-excellent food and drinks at the blackwater siren
Read more reviews

10. Lovely Key Largo rental

This two-bedroom vacation rental in Key Largo is creatively designed with tropical colors to give you the feel of the ocean even while inside the house. 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. 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.

Bayfront home with shared pool, tennis on-site, shared boat ramp!
98422 Windward Ave.
condo 2 Bedrooms 2 Bathrooms

Enjoy the oceans of Key West, Florida

Enjoy a tropical feel and international culture without leaving the country when you stay at a vacation rental in Florida Keys, USA. 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 trip.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Jaclyn is a creative writer, screenwriter, entrepreneur, and social media marketer all at once. She cherishes her vacation and travel breaks because she gets to let her hair down and discover new...Read more

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