
Holiday rentals with a pool in Florida Keys
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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

Home in Oakland park with pool
The home and pool were beautiful and perfect for our Taylor Swift weekend!

Modern Villa with Pool Hollywood Hard Rock Casino
Great house for a big group - loved the pool

Hard Rock Villa - House With Pool & Selfie Walls
Joseph was a great host and we will definitely be coming back to his house. The house was exactly as described. Joseph was very responsive. The board games and books were a great touch to help keep the kids entertained during the Florida rain. We really enjoyed the pool area and the picture walls as well. It was easy to locate the house and enjoyed having a park right by the house.

Urban Oasis With Pool at West Wynwood/Allapattah
The house was really nice, especially the pool. Great layout and large kitchen. The only thing to optimize would be if there were more chairs outside and the table would be repaired.

Hidden Gem in Miami with Heated Pool
We had an awesome stay at Cynthia's property. The location is great. It's outside of Miami far enough where you don't have a crazy amount of traffic but close enough for a short to medium length drive to other destinations & attractions. The property is fantastic. it is well maintained, clean and very spacious (there were 4 in our party). The neighborhood is nice and feels very safe. We took many walks around the area. There is some traffic noise but by no means a deterrent for choosing this property. For us the pool is a highlight. It's a large pool & deck and the water is kept warm. Cynthia is a great host. She provided and responded to all communications very timely. Overall, I highly recommend this property.

Large Waterfront House with Pool 4bd/2ba
Chris and Jamie were always available and reached out during our stay to make sure we were good. I wish construction wasn't going on because it was pretty noisy but that's not their problem. Very close to Ft Lauderdale airport. And the place was clean. Thank you

Beautiful Home w/ Pool & Spa, Pet Friendly!
We very much enjoyed our stay at Dara's house. Communication with the host was easy and helpful. The house is in a quiet neighborhood not far from a major road that will lead you to all of the attractions in the Naples area. The house itself is spacious and well-laid out. The kitchen was perfect for those of us who like to cook. New appliances (everything worked) and lots of pots/pans and cooking utensils within easy reach. The bathrooms and bedrooms were a good size and there is an incredible amount of drawer and closet space. TVs everywhere, if you like that. But for us the hallmark was the heated pool and hot tub covered by a screen roof. So relaxing after a day of playing tourist. I hope I get the chance to return one day. This one's a real find!

Pet-friendly home w/ pool & steps to beach/food
The house was great and we really enjoyed the back patio & pool. There were 4 of us (two couples) and we had plenty of space and were very comfortable. The kitchen & living room area was also very nice & well furnished. I would like to thank the owner for opening up there home & allowing us to have a wonderful stay in Marco Island.
Condo rentals with a pool

Lely Resort Luxury Condo-2 Spectacular Pool/Golf
The experience with Ken started great with communications and answers to questions. When we arrived it got better, Greenlinks is a wonderful resort community and Ken’s unit is in a great location with easy access to the resort amenities. Never having been to Naples we were pleased with the easy access to downtown, and to Marco Island, we also headed up to Fort Meyers for a spring training game, 45 minutes door to door. Ken had a good list of restaurant recommendations, and readily gave a few more based on asks from my wife and I. We were 6 for 6 on those that we tried, all of them small local spots. The home was equipped as described, really had everything you would need. We cooked in a couple of nights, and that was no problem. It was a short walk to the pool, plenty of lounge chairs to soak up Florida sun, especially after leaving home at 19 degrees, lovely pool and club house with a small fitness center, great place for morning and evening walks Ken is a great host, see u 2026

Gorgeous Condo with 2 Bedroom, 2 Bath, Pool
Jenifer and Wally were great hosts. Communication was proactive and very helpful. The condo was great. It had everything we needed and more including all kitchen essentials and beach essentials. The location is perfect being 15 minutes from either Marco Island or downtown Naples. I would highly recommend staying here and would definitely come back. Thank you Jenifer and Wally for having us!

Modern Spacious 2 Bed In Aventura/ FREE Parking
I recently stayed at a beautiful apartment in Miami, hosted by Dmitry and Maria, and we couldn't have been more pleased with the experience. The apartment offered stunning views of the water and boats, making every moment feel like a picturesque escape. It was impeccably clean, which added to the overall comfort and enjoyment of the stay. Dmitry and Maria were incredibly kind and flexible, always available whenever we needed assistance, making the entire process smooth and pleasant. The beds were comfortable, the bathrooms were very nice, and the kitchen was fully equipped.I highly recommend this apartment for anyone looking to visit Miami.

Luxury 1/1 Beach Condo *No resort Fee* Pools, Gym
Fantastic location, minute walk to the beach and restaurants. Great amenities in the building, the pool area has an amazing view. Will hopefully be back soon!

Modern 1BR +Free Parking Pool Gym @Miami Design
Beautiful building, very clean, everything you could need from an apartment. Loved the bbq and pool area on the 6th floor. Only slight issue was the noise from the road at night but it’s to be expected in a lively city like Miami. Dani was a great host!

ON CANAL! Pool+Walk to BEACH! Boat Watch! 2b/2b
This place was amazing! Clean, cozy. great communication from the host, We spent a lot time poolside watching boats go down the canal! It’s Walking distance to the beach and local restaurants. She also supplied everything you need for a day at the beach! We will definitely stay again!

Oceanfront Remodeled Beautiful Condo
We had a great time on our vacation. The condo was clean and comfortable, the beach was beautiful, and there were lots of great restaurants and stores within a half mile.

Casa Di Napoli: 2/2 Chic Retreat/Private Pool
Super clean and private, loved the hot tub and pool.
Home rentals with a private pool

Sandcastle of Marco Island Waterfront Private Pool
Relaxing area. Really enjoyed the view and the pool. Dockside sitting area was beautiful. We even had a dolphin swim up to the dock to take a look at us!

Plantation Acres Mansion
Good Place to stay , location was great close by to everything you need. House was accurate to its description. No issues whatsoever perfect for large family or friends. Peaceful neighborhood.

Sunset House
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.

Private Luxury Spanish Style Home W Private Pool
Although this location is much closer to Ft. Lauderdale than Miami, it was beautiful and spacious. We felt safe and loved the pool! Would definitely recommend.

Private Villa with Pool, Sauna, Billiard
great place

Lighthouse 1124
Great stay and location, beautiful house and property, we felt right at home! House was very clean and comfortable. Host was very responsive we would stay again!
Destinations to explore
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