
Vacation rentals with a pool in Florida Keys
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Florida Keys
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Florida Keys rentals with a pool
House rentals with a pool

Cancellation Deal: 07/26 thru 08/09
Eddie’s place was perfect for our family vacation! It was beautifully furnished and decorated. The house was clean and clutter free. There were plenty of linens and towels. The kitchen had everything you need and was well organized. The pool area was so relaxing. The location was incredibly convenient to grocery stores and activities as well as just a short walk to the beach which also had a park and great playground for kids. We hope to come back again soon!

Cudjoe Key Home with a View
Everything was great. We enjoyed the pool, pickleball, and the water. The house was perfect for the area. Definitely recommend!

Gorgeous Marco Island Pool Home near Mackle Park!
This was the perfect house for a family with small kids. We bikes to the park and walked the trail. Everything was 5 minutes away. Gist was perfect, provided everything we needed and answered all questions. Wonderful first time in Marco island, would rent this place again for sure!

Top-rated luxury pool home in prime location
Our family of four had a great stay at Kate's property. It is in a great location close to beaches and restaurants yet private enough to really be able to relax quietly by the pool. The house is spacious and had all of the amenities we needed for a terrific vacation.

•Floasis• Your private FL oasis 5 min to beach!
Cristina has made a very special place to enjoy with your family/ friends. I felt right at home, and my son started walking alone as soon as he arrived, but he didn’t stop, lol 😆 . That’s the type of energy Cristina Airbnb brings to the table. Keep up the fantastic job. I can’t wait to try one of your other places :)

Bohemian Beach Bungalow
The Bohemian Beach Bungalow is amazing! My husband and I can't talk enough about what a wonderful time we had. It was literally one of our best Airbnb stays. Karen our host was great. She answered all our questions so quickly and was very accommodating. Everything is brand new in the house, and it was immaculate inside. We will definitely be returning next year and can't wait. I will be telling all my friends about this amazing find! Thank you, Karen, for a wonderful vacation!!

Rise And Shine On The Water
There were five of us in the house and we felt immediately comfortable. Everything was super clean. The location right on the water was overwhelming as expected. Everything that is needed was there. The kitchen and terrace were very large and the mattresses were very comfortable. Key West is about 30 minutes away. Check-in and check-out as well as contact were completely unproblematic. We will be back!

Anglers Terrace, Condé Nast Traveler's Best Airbnb
We really enjoyed this home in Marathon. Sitting by the canal for morning coffee, swimming in the pool on a hot afternoon, having dinner on the covered porch, or plying corn hole on the roof… it was all super enjoyable. Andy even dropped off some wonderful bagels one morning! The location is super close to all that Marathon has to offer. We would recommend this home to anyone
Condo rentals with a pool

Feels Like Summer ~ Panoramic Water Views! 2BR
Wow! What a fabulous apartment! We had the most amazing stay to celebrate my birthday! This apartment had everything we needed, a home from home! Immaculate throughout and in such a central location with AMAZING views!! These hosts were fantastic! Thank you so much! If you’re looking to stay in Miami, this is the one to book!

Gorgeous lagoon-front 2BR Townhouse with 2 pools
Would definitely rent again! Relaxing with plenty of outdoor spaces to enjoy. Comfortable condo with everything you need.

Luxurious Suite+Open Ocean Views+Pool & Cabana Bar
This was a great place to stay in Tavanier! Very close to Key Largo and a short drive to all the charters and activities in Islmarada. Very roomy condo with every at home convenience. Great community pool that had food and drinks available on site from Island Grill. Will definitely consider staying here again. Also.....our host "Largo" was great to deal with. Nice, Friendly, and quick to answer any questions. My boys and I had a wonderful stay!

Beachfront and Lovely Unit Near Aventura Mall
Nice apartment on the beach with a gorgeous view. Just was super easy to get ahold of and helped us to check in early. 10/10 would recommend!

Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba
Laurie and Co. were so responsive and welcoming. The place is beautiful and the amenities are lovely. Much like the other reviews, we had a wonderful stay and totally recommend this place!

Sugar Cane - Florida Keys tropical retreat
Had a great time here. Enjoyed the beach and pool along with the location.

Keys Life Ocean Pointe Pool Jacuzzi Beach Crib
My family had a wonderful time. The property was clean and well-appointed. Responses from our hosts were always super-quick. I highly recommend!

Ocean View Corner Penthouse Ocean Pointe 5416
Beautiful condo… met our needs plus…resort was perfect…great location…..very satisfied with this experience
Home rentals with a private pool

Private Villa with Pool, Sauna, Billiard
It was perfect. We will definitely come back.

Sandcastle of Marco Island Waterfront Private Pool
Our family came to Marco Beach for our school spring break. What stood out about this house with how close it is to everything. We loved being able to walk to restaurants, coffee, shops, and even the grocery store. The inside of the house was perfect for what we needed. We also greatly enjoyed the pool as well as being able to sit on the dock and look out at the water. Denise, the homeowner, was very easy to work with and was great about giving us recommendations of different things that we could see or do while there. I would highly recommend this property to anybody who is coming to Marco Island, and looking for a place where they can kick back unwind and really enjoy themselves. We will absolutely be back.

Magnificent Gulf View Condo
The host was responsive and helpful. Fantastic location and views of the ocean! Three pools and three hot tubs, private beach, gym, pickle ball, basketball, etc. so lots to do for families with kids. Beautiful condo, clean, modern, and updated. Peaceful, gorgeous spot on Marco Island - highly recommend!

Lighthouse 1124
Great place to stay in Marco Island. Some minor issues but the host and management are very responsive.

Luxury Waterfront Home Minutes from the Beach
We LOVED our stay in Fort Lauderdale. The place was absolutely beautiful and just like advertised. We had to make a last minute reservation and the hosts were more than accommodating and extremely responsive. We traveled with a family of 6 and the home was the perfect size for us as there was more than enough room and we all had our own bathrooms. The outside area was amazing. The kids loved the pool and it was a very nice quiet, well kept neighborhood. Anytime I had a question I was able to text the hosts and they responded to me almost immediately. I even accidentally sent an amazon package to the wrong address and they offered to bring it to UPS for me. I cant say enough great things about this place, it was close enough to everything that you would need but also private enough to be able to relax when needed. We will definitely be back to Fort Lauderdale and would love to rent this wonderful home again.

Incredible Beach Getaway Condo W Resort Amenities

New! Gulf-View Condo with Resort-Style Amenities

Private 2br Side Ocean View at Hyde Beach Resort
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- Bayfront Park
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Trump National Doral Miami
- Crandon Beach
- Phillip and Patricia Frost Museum of Science
- Key Biscayne Beach
- Coral Castle
- Hobie Island Beach Park North
- Biscayne National Park
- Fairchild Tropical Botanic Garden
- Conch Key
- Biltmore Golf Course Miami
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- Miami Seaquarium
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- EAA Air Museum
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