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

Heated Pool Home with Private Landscaping
Tim & Tammi took care of all issues that came up. Very responsive & helpful. The heated pool was a real treat, used it every day !

Tropical Getaway w/Pool 15 Min to the Beach
The home and pool were beautiful and perfect for our Taylor Swift weekend!

2223 Doud Street, Sarasota, FL
This home was perfect for our group. We loved having 3 en-suite master bedrooms. The location is great for beach(Siesta Key), waterfront restaurants and shopping. We would definitely book again!

A Slice of Paradise pool and pool table
Excellent communication with hot. Very easy to reach. Large home, very comfortable.

Pool/3BR 11 min SJU airprt/beach
I have to say I would definitely stay again. Terrence was a great host, responds to message super quick and really helpful. The place was in excellent condition, very secure place very clean. The location is really close to a lot of things, 17 mins away to old San Juan, 9 mins to Walmart and other restaurants. Even though less than 24 hrs into our stay the island had a total blackout Terrence was really helpful. Checked on us throughout the day, making sure we were ok. Really did appreciate that. You may see the neighborhood to be a little sketchy but to be honest it is a very very quiet neighborhood. Thank you Terrence for opening your home.

Hidden Gem in Miami with Heated Pool
Cynthia was so sweet and helpful always responsive would love to stay here again I will be back soon !

2 bdr. house with private pool Villa 704
Great place,very clean and new,everything worked

Green Hills House
100% recommendation the house is very comfortable exactly the same as the pictures!!!! Clean and organized…. Super shared with my family…. I loved it!!!!!
Condo rentals with a pool

Modern BEACH Condo in Peaceful Hutchinson Island
We had a much needed, relaxing vacation in Yusmany’s condo. The place is well equipped and we especially appreciated the variety of beach towels and equipment since we expected to have to purchase our own. Loved the rocking chairs on the porch and the proximity to the beach, pool and condo restaurant. Thank you!

Spacious 2 Bedroom Luxury Condo.
This was our second stay at Browne’s Condominiums, which offers an excellent location—conveniently situated near a small shopping center and within walking distance of a grocery store (1.4 km) and the beautiful Carlisle Bay (3.4 km) renowned as one of the top beaches in the world. If walking is not your thing, buses, vans and taxis are plentiful to get you to your destination. Toby’s place provides a warm and inviting atmosphere, making it an ideal retreat for small families or couples. We encountered a minor issue with a piece of furniture, but it was addressed promptly and effectively. Given its increasing popularity, I found it fully booked for 2026, which speaks to its appeal. I highly recommend considering this condo for your stay, you will not be disappointed. We look forward to returning!

Serenity Ocean 2 Luxury condo —Parking Included
The facility was beautiful and the condo was equally as nice. Looking forward to booking there again next year.

Perfect Location 3bd2ba CondoVacation/Business
Brad & Juanita condo was just right bed was conftoble water pressure was good The location was perfect, with many beaches nearby and We enjoyed exploring the area and found plenty of great dining options nearby. , our experience was amazing. We would highly recommend

ON CANAL! Pool+Walk to BEACH! Boat Watch! 2b/2b
We really enjoyed the one night we spent here before a cruise. The directions and instructions were clear and the pictures matched the place. The kids really enjoyed the swimming pool and all the extra beach towels were really helpful. Overall, this was a great option for us. It was also a couple blocks from the beach and walking distance to some restaurants. We will book again in the future.

Dreamy pool side condo
Diana our stay was excellent !!! we hope to return, incredible everything from the friendliness of the people in charge to welcome us to you! Thank you very much, we were happy staying there

Peaceful retreat, pool, hot tub, near Siesta Key!
Absolutely beautiful home close to everything. Privacy was the key and home had everything and more! The most important was the communication and the host nailed it! I will definitely be back!

Quiet , pool, gated,security
One of the best air bnbs I stayed in hands down! Definitely booking again on my next return.
Home rentals with a private pool

Gorgeous Colonial House near Cafes and Bars
Fantastic location in the Colonial Zone where everything is well within walking distance. Being in the midst of it allows you to experience the history and culture of the area. We felt very safe and residents were friendly and helpful. A great plus was having Susanne’s taxi friend available for transportation needs. Besides picking us up from the airport initially, we hired him to take us to the north end of the country and bring us back to Santo Domingo later. He goes anywhere in the country and gives a great rate to those who stay at Susanne’s property. We really enjoyed the total privacy of this roomy property. It has a nice plunge pool to relax in at any time. We’ve stayed at a number of airbnbs and this was one of our favorites.

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.

Soak up the Beachy Vibe at a Vibrant Poolside Paradise
We just returned home from a stay at Amy’s home and it was wonderful. The house matched the pictures, was clean, well equipped, and very comfortable. The Flamingo Park location was with an easy walk to several restaurants and we were able to easily walk to Palm Beach Island as well. The Flamingo Park neighborhood is quiet and very cute. We also loved the heated pool and poolhouse with refrigerator and bathroom. It was our own personal paradise for the week we were there and we would definitely recommend it. Amy was also very friendly and responsive from the start, often answering requests from me in minutes. Between the host and house, five stars all the way around.
Casa Pantheon Luxury Colonial House
This was my second full-week stay at Casa Pantheon and once again, it was incredible. My first trip was August 2023 for my birthday and bachelor party. This time, it was for my friend’s first international trip and his birthday. We stayed from April 2–10, 2025. The property is beautiful, well-maintained, and perfectly located in the heart of Zona Colonial. The jacuzzi, sauna, and pool made it even better. Walking distance to great restaurants, bars, and historical sites. Pierre is an outstanding host — very responsive and professional. Every detail from check-in to check-out was seamless. Whether it’s your first visit or a return trip, Casa Pantheon gives you a real Dominican Republic experience. Thank you again, Pierre — we’re already looking forward to coming back!

Old City Villa - Breakfast & Housekeeping Included
Sebastian is a very accommodating host and always reply’s to any questions. The property was amazing, the rooms were comfortable and clean. The staff and cleaning crew were great, they made sure we were fed breakfast and took care of our laundry needs. Lastly, Luis from security was like part of our family. We had a really good relationship with Luis from Security and developed a friendly relationship. He was always there to greet us, open the door, and advised us on how to enjoy the city. The staff made this Airbnb experience excellent. Also the property is walking distance to all of the restaurants, bars, and stores. We were very happy of how beautiful the property looked and how well managed it was by the staff.
Walled City Luxurious Townhouse With Private Pool
Amazing condo for our family of 5 (2 adults, 3 kids). Gorgeous decor, ample space, perfect location. Easy to walk to the lively areas of the walled city, but the condo itself was extremely peaceful. Perfect combination. Katia and Rosa were amazing! Rosa’s food was delicious. Ivan was also very responsive and kind in our communication. I would definitely want to stay here again for my next trip to Cartagena.

Condado Beach Views by Cesar 2501
This was our first time in Puerto Rico & we’re glad we were able to stay in such a nice Airbnb with no problems and a great host that was quick with the responses and super friendly. The property exceeded our expectations and we were blown away with how nice it was. The view alone was breathtaking. We would definitely stay again in the future!

Tropical Cabana with Pool in West Palm Beach
Chris is an extraordinary host. We were delighted to spend a relaxing vacation at her home. Expect a tranquil setting and the cabana is an excellent remote office. We were delighted to have the opportunity to meet Chris and could not thank her enough for her warmth, kindness and care. The spaces are as pictured and the areas are well stocked with all you need.
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