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Holiday rentals with a pool in Florida Keys

Find and book unique homes with a pool on Airbnb

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Popular amenities for Florida Keys rentals with a pool

House rentals with a pool

Superhost
Home in Fort Lauderdale
4.73 out of 5 average rating, 44 reviews

Home in Oakland park with pool

DeniseRating, 5 stars4 months ago
The home and pool were beautiful and perfect for our Taylor Swift weekend!
Superhost
Home in Fort Lauderdale
4.74 out of 5 average rating, 57 reviews

Modern Villa with Pool Hollywood Hard Rock Casino

RAchelRating, 5 stars5 days ago
Great house for a big group - loved the pool
Guest favourite
Home in Hollywood
4.92 out of 5 average rating, 154 reviews

Hard Rock Villa - House With Pool & Selfie Walls

PatriciaRating, 5 stars1 week ago
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.
Superhost
Home in Miami
4.88 out of 5 average rating, 144 reviews

Urban Oasis With Pool at West Wynwood/Allapattah

JilRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Miami
4.95 out of 5 average rating, 41 reviews

Hidden Gem in Miami with Heated Pool

RodneyRating, 5 stars2 weeks ago
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.
Superhost
Home in Fort Lauderdale
4.84 out of 5 average rating, 154 reviews

Large Waterfront House with Pool 4bd/2ba

TamaraRating, 5 stars3 weeks ago
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
Top Guest favourite
Home in Naples
4.97 out of 5 average rating, 34 reviews

Beautiful Home w/ Pool & Spa, Pet Friendly!

DavidRating, 5 stars3 weeks ago
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!
Superhost
Home in Marco Island
4.54 out of 5 average rating, 13 reviews

Pet-friendly home w/ pool & steps to beach/food

RandyRating, 5 stars4 months ago
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

Guest favourite
Condo in Naples
4.93 out of 5 average rating, 156 reviews

Lely Resort Luxury Condo-2 Spectacular Pool/Golf

MichaelRating, 5 stars1 week ago
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
Guest favourite
Condo in Naples
5 out of 5 average rating, 28 reviews

Gorgeous Condo with 2 Bedroom, 2 Bath, Pool

JessicaRating, 5 stars3 months ago
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!
Guest favourite
Condo in Miami
4.89 out of 5 average rating, 19 reviews

Modern Spacious 2 Bed In Aventura/ FREE Parking

CarolinaRating, 5 stars4 days ago
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.
Guest favourite
Condo in Fort Lauderdale
4.8 out of 5 average rating, 71 reviews

Luxury 1/1 Beach Condo *No resort Fee* Pools, Gym

DominicRating, 5 stars3 months ago
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!
Superhost
Condo in Miami
4.69 out of 5 average rating, 35 reviews

Modern 1BR +Free Parking Pool Gym @Miami Design

StevenRating, 5 stars7 months ago
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!
Superhost
Condo in Pompano Beach
4.85 out of 5 average rating, 277 reviews

ON CANAL! Pool+Walk to BEACH! Boat Watch! 2b/2b

KurtRating, 5 stars1 week ago
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!
Top Guest favourite
Condo in Sunny Isles Beach
5 out of 5 average rating, 28 reviews

Oceanfront Remodeled Beautiful Condo

BelindaRating, 5 stars6 days ago
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.
Guest favourite
Condo in Naples
4.88 out of 5 average rating, 32 reviews

Casa Di Napoli: 2/2 Chic Retreat/Private Pool

DaveRating, 5 stars1 month ago
Super clean and private, loved the hot tub and pool.

Home rentals with a private pool

Home in Marco Island
4.81 out of 5 average rating, 16 reviews

Sandcastle of Marco Island Waterfront Private Pool

LaureRating, 5 stars1 week ago
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!
Villa in Plantation
4.18 out of 5 average rating, 11 reviews

Plantation Acres Mansion

CarlonRating, 5 stars4 months ago
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.
Top Guest favourite
Home in Fort Lauderdale
5 out of 5 average rating, 19 reviews

Sunset House

JenelleRating, 5 stars4 months ago
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.
Villa in Miami
3.13 out of 5 average rating, 8 reviews

Private Luxury Spanish Style Home W Private Pool

TiffanyRating, 5 stars7 months ago
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.
Home in Dania Beach
4 out of 5 average rating, 3 reviews

Private Villa with Pool, Sauna, Billiard

ScutelnicRating, 5 stars2 months ago
great place
Home in Marco Island
4.69 out of 5 average rating, 13 reviews

Lighthouse 1124

JeremyRating, 5 stars6 months ago
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!

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