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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
The screened-in pool area features a heated pool with a clear blue surface. Multiple lounge chairs with light-colored cushions are arranged around the pool. Sunlight filters through the enclosure, illuminating the surrounding landscaped greenery.
Home in Port St. Lucie
4.83 out of 5 average rating, 18 reviews

Heated Pool Home with Private Landscaping

HerbertRating, 5 stars3 weeks ago
Tim & Tammi took care of all issues that came up. Very responsive & helpful. The heated pool was a real treat, used it every day !
Superhost
A spacious backyard features a private pool surrounded by lounge chairs and tropical landscaping. A pergola provides shaded seating, complementing an outdoor dining table that accommodates up to eight guests. The atmosphere is enhanced by clear blue skies and vibrant greenery.
Home in Fort Lauderdale
4.73 out of 5 average rating, 44 reviews

Tropical Getaway w/Pool 15 Min to the Beach

DeniseRating, 5 stars6 months ago
The home and pool were beautiful and perfect for our Taylor Swift weekend!
Guest favorite
The screened-in pool area features a clear, inviting swimming pool surrounded by a spacious deck. Natural light filters through the screen, highlighting the lush greenery visible in the background, creating a tranquil and private atmosphere.
Home in Sarasota
4.97 out of 5 average rating, 58 reviews

2223 Doud Street, Sarasota, FL

MicheleRating, 5 stars1 month ago
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!
Superhost
An outdoor space features a large swimming pool with a spa, surrounded by a wooden deck. Several chairs are placed around the pool area, and a wooden fence provides privacy. Lush greenery is visible in the background under a clear blue sky.
Home in Port St. Lucie
4.7 out of 5 average rating, 82 reviews

A Slice of Paradise pool and pool table

MariaRating, 5 stars2 weeks ago
Excellent communication with hot. Very easy to reach. Large home, very comfortable.
Guest favorite
A swimming pool is situated within a gated area, surrounded by palm trees and clear blue skies. The pool features a shallow ledge and steps for easy access. Sunlight reflects off the water, creating a bright and inviting atmosphere.
Home in San Juan
4.91 out of 5 average rating, 45 reviews

Pool/3BR 11 min SJU airprt/beach

LuisRating, 5 stars1 day ago
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.
Guest favorite
A heated pool is surrounded by lush greenery, with a dark blue umbrella providing shade over a white lounge chair. The serene setting is illuminated by soft lighting, creating a calm atmosphere for evening relaxation.
Home in Miami
4.96 out of 5 average rating, 47 reviews

Hidden Gem in Miami with Heated Pool

DemetriaRating, 5 stars1 week ago
Cynthia was so sweet and helpful always responsive would love to stay here again I will be back soon !
Guest favorite
The villa is showcased from an aerial perspective, highlighting a private swimming pool surrounded by a stone deck. The property's modern architecture is complemented by lush green landscaping and neighboring villas. Large glass doors provide an open view into the inviting interior space.
Home in Sosúa
5 out of 5 average rating, 5 reviews

2 bdr. house with private pool Villa 704

RonnieRating, 5 stars1 week ago
Great place,very clean and new,everything worked
Superhost
A private pool area is depicted, featuring a clear blue pool surrounded by beige stone tiles. A built-in hot tub is visible beside the pool. Decorative white gravel lines the perimeter, and a low stone wall provides privacy, with palm trees and mountains seen in the background.
Home in Guayama
4.87 out of 5 average rating, 23 reviews

Green Hills House

JulyRating, 5 stars3 weeks ago
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

Guest favorite
Condo in Fort Pierce
4.94 out of 5 average rating, 111 reviews

Modern BEACH Condo in Peaceful Hutchinson Island

DeborahRating, 5 stars2 weeks ago
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!
Top guest favorite
The well-lit pool area is surrounded by lush tropical plants and softly glowing pathway lights. The tranquil pool reflects the evening sky, and stone pathways weave through manicured gardens, offering an inviting ambiance for relaxation.
Condo in Rockley
4.91 out of 5 average rating, 147 reviews

Spacious 2 Bedroom Luxury Condo.

HeleneRating, 5 stars2 weeks ago
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!
Superhost
A large outdoor pool is surrounded by lounge chairs and tropical landscaping. Palms and greenery line the pool area, with multiple balconies overlooking the water. The pool’s clear blue water invites relaxation under a bright sky.
Condo in Boynton Beach
4.8 out of 5 average rating, 69 reviews

Serenity Ocean 2 Luxury condo —Parking Included

ToniRating, 5 stars3 weeks ago
The facility was beautiful and the condo was equally as nice. Looking forward to booking there again next year.
Guest favorite
A clear blue pool is surrounded by lounge chairs, providing a spacious area for relaxation. The pool is framed by a clean pathway and surrounded by greenery, with a basketball court visible in the background under a bright blue sky.
Condo in PR
4.83 out of 5 average rating, 179 reviews

Perfect Location 3bd2ba CondoVacation/Business

lillieRating, 5 stars1 week ago
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
Superhost
Condo in Pompano Beach
4.84 out of 5 average rating, 284 reviews

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

KylieRating, 5 stars2 weeks ago
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.
Superhost
Two inviting pools are surrounded by palm trees and lounge chairs. Clear water reflects the sun, while the shallow entry area with mosaic tiles is visible in one pool. Umbrellas provide shaded seating options near the pools.
Condo in San Andrés
4.77 out of 5 average rating, 44 reviews

Dreamy pool side condo

CamilaRating, 5 stars2 weeks ago
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
Guest favorite
A large swimming pool is surrounded by lounge chairs beneath the shade of tall trees. A separate hot tub is visible next to the pool, with a red umbrella providing shade to a nearby table. The area is fenced, offering a sense of privacy.
Condo in Sarasota
4.97 out of 5 average rating, 64 reviews

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

EmmaRating, 5 stars2 days ago
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!
Guest favorite
An illuminated rooftop pool is visible at night, with soft purple and blue lighting that reflects off the water. The view extends over a distant cityscape, featuring twinkling lights and dark hills in the background, contributing to a serene atmosphere.
Condo in Kingston
4.97 out of 5 average rating, 63 reviews

Quiet , pool, gated,security

DrevRating, 5 stars3 weeks ago
One of the best air bnbs I stayed in hands down! Definitely booking again on my next return.

Home rentals with a private pool

Guest favorite
A spacious entryway is defined by exposed brick archways and a staircase leading to the upper level. A glass-topped desk is positioned in the foreground, complemented by textured tile flooring and decorative wall art.
Home in Santo Domingo
4.94 out of 5 average rating, 401 reviews

Gorgeous Colonial House near Cafes and Bars

KentRating, 5 stars3 weeks ago
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.
Top guest favorite
The serene waterway is bordered by lush greenery and palm trees, reflecting a clear blue sky. A wooden dock is visible, with posts lining the edge and a gentle slope leading to the grassy area beyond the canal.
Home in Fort Lauderdale
5 out of 5 average rating, 19 reviews

Luxury Waterfront Home Minutes from the Beach

JenelleRating, 5 stars6 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.
Top guest favorite
A heated saltwater pool is framed by lush greenery, providing a sense of privacy. The pool features a decorative wall at one end, adding an elegant touch. The surrounding patio offers a clean, open space for relaxation.
Home in West Palm Beach
4.96 out of 5 average rating, 163 reviews

Soak up the Beachy Vibe at a Vibrant Poolside Paradise

DanielRating, 5 stars1 month 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, 329 reviews

Casa Pantheon Luxury Colonial House

DavidRating, 5 stars1 week ago
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!
Guest favorite
A dining area is positioned adjacent to a swimming pool, with a spacious table set for meals. The open layout features arched doorways, allowing for natural light to illuminate the space. Lush greenery and decorative elements enrich the ambiance.
Villa in CARTAGENA
4.87 out of 5 average rating, 152 reviews

Old City Villa - Breakfast & Housekeeping Included

AlvaroRating, 5 stars1 month 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.
Guest favorite
A private pool sits surrounded by lush ferns and a stone wall, providing a tranquil setting. A patio area features a dining table under an umbrella, creating a space for outdoor relaxation. The pool's blue tiles reflect sunlight, enhancing the serene environment.
Townhouse in CARTAGENA
4.87 out of 5 average rating, 209 reviews

Walled City Luxurious Townhouse With Private Pool

KeishaRating, 5 stars2 weeks ago
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.
Guest favorite
A modern living space is observed, featuring a light grey sofa adorned with turquoise cushions. A sleek coffee table sits in front, with decorative glass items. Large windows provide ample natural light and showcase city views, while a cozy sleeping area is visible in the background.
Condo in San Juan
4.91 out of 5 average rating, 256 reviews

Condado Beach Views by Cesar 2501

ChaseRating, 5 stars3 weeks ago
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!
Guest favorite
A serene pathway lined with tropical plants leads to a stone table, surrounded by lush greenery and vibrant palms. The path is paved with bricks, creating a welcoming entrance to a private garden area.
Guesthouse in West Palm Beach
4.97 out of 5 average rating, 172 reviews

Tropical Cabana with Pool in West Palm Beach

EileenRating, 5 stars2 months 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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