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Vacation rentals with a pool in Caribbean

Find and book unique homes with a pool on Airbnb

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Popular amenities for Caribbean 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 stars5 months ago
The home and pool were beautiful and perfect for our Taylor Swift weekend!
Guest favorite
Home in Hollywood
4.79 out of 5 average rating, 124 reviews

AmaZin spacious 4/2 Pool Home in Hollywood FLL-MIA

AdamRating, 5 stars1 month ago
We had a great stay. The house was as described and clean.
Superhost
Home in Lake Worth
4.83 out of 5 average rating, 298 reviews

#2 Lake Osborne Tropical Pool Oasis HEATED POOL

EdwardRating, 5 stars2 months ago
What a GREAT place! We are a group of four divers that dived around the east coast. The house was located close to our shore diving and boat charters. It is laid out perfectly for a small group with two vehicles.
Guest favorite
Home in San Juan
4.91 out of 5 average rating, 43 reviews

Pool/3BR 11 min SJU airprt/beach

ZacharyRating, 5 stars3 weeks ago
Terrance was amazing. Super responsive, helped us with all issues, pool is super clean, A/c was amazing. If you had to force me to say something negative, I’d be at a loss of words. I hope I can book this for the future!
Guest favorite
Home in Lehigh Acres
4.83 out of 5 average rating, 131 reviews

LIVING in PARADISE 🌴 ⛱️ 😎

ToniRating, 5 stars2 weeks ago
Dario was great. He took very good care of us and we left making a new friend.
Superhost
Home in Oranjestad
4.92 out of 5 average rating, 146 reviews

Vacation Home! Big Pool Area! Near Beaches&Center!

ToddRating, 5 stars1 month ago
We stayed for 2 weeks and absolutely LOVED the house. Each bedroom does in fact have its own bathroom. There are a total of 5 bathrooms at the house. The kitchen is well equipped with everything you need to prepare very nice meals. Coffee maker, blender, toaster, microwave, oven all worked great! The best part??? The pool area & surrounding patio! There’s a large palm tree on the southeast side of the patio that offers wonderful shade during the early part of the day. A large umbrella can also be opened for more shade. Plenty of chairs, loungers and tables are around the patio. The changing color LED pool lights at night are gorgeous! We brought a small blue tooth speaker to add to the ambiance of the pool area. We used the patio’s gas grill 4-5 times and it works great! Right across the street is a grocery store and hardware store. Super convenient!! Overall a wonderful, safe, private and amazing place to stay! Definitely will do again!!
Superhost
Home in Fort Lauderdale
4.84 out of 5 average rating, 157 reviews

Large Waterfront House with Pool 4bd/2ba

CoriRating, 5 stars3 weeks ago
Place was easy to check in to with a video instruction. The host was very responsive and even gave us a last minute later check out to help with our needs.
Guest favorite
Home in Miami
4.94 out of 5 average rating, 103 reviews

Sunny Getaway: Relaxing Miami Home

NicoleRating, 5 stars2 weeks ago
This was our second time staying at this Miami home within the last couple of years and it was perfect for visiting family close by and spending time together. Once again, we had so much fun swimming in the pool and relaxing poolside! Plenty of beds, bathroom, and hanging out space inside for the whole family.

Condo rentals with a pool

Guest favorite
Condo in Naples
4.93 out of 5 average rating, 157 reviews

Lely Resort Luxury Condo-2 Spectacular Pool/Golf

MichaelRating, 5 stars1 month 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
Top guest favorite
Condo in Rockley
4.91 out of 5 average rating, 145 reviews

Spacious 2 Bedroom Luxury Condo.

CarolineRating, 5 stars3 weeks ago
The condominium is a 5 minutes walk from the main highway with Tapas, Salt and the boardwalk right there. The grounds, pool area, gym and barbecue area are really lovely. Everything is well maintained and private either great security on the complex however this is a lovely neighbourhood so always felt safe. Tony was very accommodating and allowed us a late check out. Really recommend.
Superhost
Condo in Boynton Beach
4.8 out of 5 average rating, 69 reviews

Serenity Ocean 2 Luxury condo —Parking Included

ToniRating, 5 stars4 days ago
The facility was beautiful and the condo was equally as nice. Looking forward to booking there again next year.
Guest favorite
Condo in PR
4.83 out of 5 average rating, 174 reviews

Perfect Location 3bd2ba CondoVacation/Business

FrancesRating, 5 stars3 weeks ago
we would return back and highly recommend family & friends
Superhost
Condo in Pompano Beach
4.85 out of 5 average rating, 278 reviews

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

MyrnaRating, 5 stars3 weeks ago
Great view and wonderful place to stay!
Guest favorite
Condo in Sarasota
4.97 out of 5 average rating, 61 reviews

Peaceful retreat, pool, hot tub, near Siesta Key!

JulieRating, 5 stars3 months ago
Great place to stay! It was a very safe community with nice extras and was pretty close to the beaches. So nice to have the extra beach supplies to go shark tooth hunting at Caspersen Beach. The condo was clean and spacious.
Guest favorite
Condo in Prospect
4.85 out of 5 average rating, 27 reviews

Serene and Secure 2 Bedroom Condo with Pool and AC

MarcinRating, 5 stars1 month ago
It was a great stay. The place looks much better than in the pictures, it is perfectly equipped and Terese sent very precise instructions on how to use the apartment. The contact was fast and very nice. The property is very spacious and clean, has an amazing view. I highly recommend using this property.
Guest favorite
Condo in Bonita Springs
4.93 out of 5 average rating, 113 reviews

Amazing Condo-1 mile from Bonita Beach

LisaRating, 5 stars1 day ago
Can not say enough about this condo! Everything was perfect and clean. The master bedroom was my favorite. The leather reclining furniture and mounted huge big screen TV was a plus also. The pool was very nice. Loved that everything is so close to get to. Beaches was beautiful. Susan was the best host with all the info and even let us know the place was ready and clean for whenever we wanted to check in. Will be staying here again for sure!! Thank you, Lisa West!

Home rentals with a private pool

Guest favorite
Home in Santo Domingo
4.94 out of 5 average rating, 398 reviews

Gorgeous Colonial House near Cafes and Bars

DawnRating, 5 stars1 week ago
Beautiful home that looked exactly like the pictures. It was very clean and very relaxing. It was bigger than expected! Tons of space. I would stay here again. The only thing I would like to mention is the stairway to go upstairs to the second floor and also the stairway to get up to the rooftop patio are not child friendly or if you are older and have trouble with mobility you should expect not to be able to go up those stairs. The kitchen has every possible thing you could need, and the bathroom and bedrooms were all well equipped as well! Derserves more than 5 stars really.
Top guest favorite
Home in West Palm Beach
4.96 out of 5 average rating, 162 reviews

Soak up the Beachy Vibe at a Vibrant Poolside Paradise

DanielRating, 5 stars3 weeks ago
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.
Guest favorite
Villa in Santo Domingo
4.93 out of 5 average rating, 327 reviews

Casa Pantheon Luxury Colonial House

ScottRating, 5 stars1 week ago
Pleasant stay. Perfect, convenient location and a beautiful home.
Guest favorite
Villa in CARTAGENA
4.87 out of 5 average rating, 151 reviews

Old City Villa - Breakfast & Housekeeping Included

AlvaroRating, 5 stars2 weeks ago
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.
Superhost
Bungalow in Punta Cana
4.79 out of 5 average rating, 318 reviews

Sink into the Pool of a Wonderful Bungalow

RachelRating, 5 stars2 weeks ago
My husband and I went for a quiet vacation and wanted to stay away from the crowds with more privacy and this was perfect. The pool was relaxing, the outside shower my husband loved, the bed was comfortable, and all the amenities you needed. Only two things: the washing machine didn't work, and the water turned off periodically but that's not the fault of the owners. Would come again!
Guest favorite
Townhouse in CARTAGENA
4.87 out of 5 average rating, 207 reviews

Walled City Luxurious Townhouse With Private Pool

GayleRating, 5 stars1 month ago
The house was gorgeous in a beautiful neighborhood in the walled city, secure, easy walking distance to the rest of the walled city as well as Getsemani. The pool was fantastic and refreshing and beautiful. ( we didn’t use the hot tub as it was very hot in Cartagena) Loved all the outdoor spaces in the unit and in the common areas. The women who cooked and cleaned for us were exceptional, providing us with breakfast every day and a special luncheon and dinner for 13 people. They took care of us in every way.
Guest favorite
Condo in San Juan
4.91 out of 5 average rating, 253 reviews

Condado Beach Views by Cesar 2501

MarcusRating, 5 stars3 weeks ago
This apartment has an amazing and spectacular view. Very clean and organized. It’s situated where all the restaurants are. Beach is 2minutes walking distance. I would definitely stay here next time I come Puerto Rico
Top guest favorite
Guesthouse in West Palm Beach
4.97 out of 5 average rating, 172 reviews

Tropical Cabana with Pool in West Palm Beach

EileenRating, 5 stars1 month ago
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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