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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

Guest favorite
A serene outdoor area features a vibrant blue swimming pool surrounded by natural stone tiles. Lush greenery lines the space, while rustic brick walls and open columns create a seamless connection to the interior. Comfortable seating is visible in the background.
Home in Cartagena
4.9 out of 5 average rating, 101 reviews

Casa Linda

SaraRating, 5 stars1 month ago
Beautiful home excellent location
Guest favorite
An aerial view of a modern villa surrounded by lush greenery. The exterior features large glass windows and a private pool, accompanied by sleek lounge chairs on the deck. The open layout invites natural light, showcasing the villa's seamless connection to its outdoor surroundings.
Home in Providenciales
4.96 out of 5 average rating, 339 reviews

Villa Cocuyo Micro Villa with pool

JasmineRating, 5 stars1 week ago
This was the perfect couples getaway. This villa was in the perfect location, close to the airport and about 10-15 mins away from all the hotels and local shops. I would recommend renting a car it's cheaper for sure. Jeffrey was very responsive and let us check in way earlier than planned, he also had drinks in the fridge for us which was so kind of him! We explored all the beaches and Jeffrey had some beach chairs that we could borrow which was great. If I could add something to the villa it would be a full length mirror for those outfit checks :) Overall, 10/10 experience and would definitely book again.
Top guest favorite
Home in San Nicolas
5 out of 5 average rating, 148 reviews

Ocean Front Family Vacation Home, at Baby Beach

KaylaRating, 5 stars2 weeks ago
I can’t say enough how lovely this home was. I have never stayed at an Airbnb so well equipped. It had everything we could possibly need and more, and made travel with young kiddos so much easier. Joost provided beach chairs, umbrellas, snorkels, sand toys, pool toys and so much more. The kitchen had every appliance, pan, utensils you could need, and the place itself was just beautiful with the most beautiful view. This place is a MUST STAY. Thank you Joost for putting so much thought into your place it was truly the most perfect stay.
Top guest favorite
A private pool with a waterfall feature is set within a spacious outdoor area. Surrounding the pool, light-colored tiles contrast with dark stones, while tropical plants add greenery. The clear water reflects sunlight, creating a peaceful atmosphere.
Home in Aguadilla
5 out of 5 average rating, 207 reviews

Suite with Private Pool

MariahRating, 5 stars1 day ago
Casa Santiago was just what the pictures and descriptions said. The host was thorough in his communication from check in to check out. Prior to arriving, they sent us a list of places to eat and things to do. Our only regret is that we didn't stay longer. We will definitely be returning here when in PR!
Guest favorite
An infinity pool with tranquil water reflects the surrounding greenery and sky. A sun lounger in a natural tone is positioned beside the pool, offering a relaxing spot to enjoy the view. Wooden decking frames the pool area, enhancing the serene atmosphere.
Home in Sosúa
4.97 out of 5 average rating, 177 reviews

Waterfall House

DonnellRating, 5 stars3 weeks ago
The host was extremely professional. The house was exactly what is seen in the pictures. I would definitely recommend it to anyone looking to have a fun and peaceful vacation.
Superhost
Home in Puerto Nuevo
4.87 out of 5 average rating, 116 reviews

"Seaside Luxury" - Ocean Front, Private Pool, Wifi

JamesRating, 5 stars1 week ago
this was a great experience for our family. the location is great as it's right on the beach and just 40 minutes from San Juan. having now driven around the area a lot I do enjoy vega Baja where the house is more than surrounding areas. great local beach is close as well. the house is clean and comfortable. great kitchen for cooking. good Internet I worked a couple days. and amazing AC if you need it. just like the pictures show
Top guest favorite
A private pool is surrounded by vibrant greenery and palm trees, providing a tropical ambiance. Two wooden chairs with soft cushions sit at a small table, with clear water glistening in the pool. The ocean can be seen in the background, adding to the serene setting.
Home in Willemstad
4.95 out of 5 average rating, 158 reviews

Private Oceanfront luxurious city villa with pool

KaylaRating, 5 stars2 weeks ago
Everything was great! The hosts were great communicating and checking in on us throughout our stay. They also gave us a ton of reccomendations. The location is amazing for exploring the town and different restaurants/beach clubs. It is within walking distance to a ton of places. Its right in the center of the island as well so its super quick driving to any side of the island etc. The only recommendation I have is to get some good bug spray. You want to leave the doors/windows open for airflow and the mosquito's were really bad when we went (which I have that issue in general, they just eat me up, my husband didn't get bit too badly) but I would reccomend getting some sort of mosquito repellent or bug catcher bags etc. to place in the house. The bedroom has the A/C unit, we were very comfortable sleeping at night. It was a great experience overall!! I would definitely recommend if you're looking for a more local feel/vibe for your stay!
Guest favorite
An infinity plunge pool extends toward Culebra's landscape, featuring a gentle waterfall. Potted plants frame the view of the bay, where the sun sets behind rolling hills, casting warm hues over the water. The tranquil scene emphasizes the home's connection to its natural surroundings.
Home in Culebra
4.94 out of 5 average rating, 444 reviews

Casa Maya @ Hilltop (private infinity plunge pool)

EmmaRating, 5 stars2 weeks ago
The space is perfect for two — we were there almost a week! Loved the plunge pool and the deck for sunbathing. Kavita was a wonderful host, and gave us many tips and recommendations for navigating Culebra, including where to rent a Jeep, a captain to hire for our Culebrita adventure, etc. You’ll definitely want a Jeep vs a golf cart — the hill to the house is no joke. You’ll basically be located equidistant from all of the best beaches (we loved Tamarindo and Zoni; Flamenco also fun it a totally different vibe!) +1 to being in a solar-powered place!! We had ab island wide power outage that we never even noticed.

Condo rentals with a pool

Superhost
A clear swimming pool is shown, reflecting the blue sky and surrounding greenery. Palm trees are visible in the background, adding tropical ambiance. The pool area features a white fence, contributing to a feeling of privacy and security.
Condo in Luquillo
4.88 out of 5 average rating, 328 reviews

Breathtaking Oceanfront Bedroom and City Views

SoryRating, 5 stars2 weeks ago
I had a great time in Luquillo, beautiful and many things to do around.
Top guest favorite
A large pool area is visible, featuring multiple lounge chairs with orange cushions and umbrellas. The infinity pool merges with the horizon, offering unobstructed views of the sea at sunset. A serene atmosphere is created by the smooth water and open space surrounding the pool.
Condo in CARTAGENA
4.93 out of 5 average rating, 180 reviews

Luxury Oceanfront - Bocagrande Tourist Sector.

Luther PaulRating, 5 stars6 days ago
I had a fantastic stay at this Airbnb! The impressive amenities, including a beautiful pool and two bathrooms, made it incredibly convenient for our group. The spacious terrace with unobstructed views of the beach and water was a perfect spot to relax. The area is very walkable, with easy access to the airport and nearby attractions in Cartagena. I came down for a quick celebration for my brother-in-law, but I’m already looking forward to returning to explore more of this vibrant city. Huge thanks to Maria for being an exceptional host! Highly recommend!
Superhost
A refreshing swimming pool is located on the outdoor deck, surrounded by lounge chairs and modern high-rise buildings. The clear blue sky is visible, with a few clouds adding to the serene atmosphere. The Bank of America building stands prominently in the background.
Condo in Miami
4.86 out of 5 average rating, 156 reviews

Chic Studio 5 Icon Brickell Amazing View

JordanRating, 5 stars2 weeks ago
The place was amazing and much more spacious than the pictures showed. Amenities were 10/10!! Elevators were a bit slow but it was a lot of floors so I understand. Highly recommend
Superhost
A rooftop pool with clear blue water is surrounded by lounge chairs on a wooden deck. The expansive view includes city buildings and the horizon. An umbrella and small tables are positioned near the pool, providing options for relaxation and socializing.
Condo in Santo Domingo
4.85 out of 5 average rating, 124 reviews

Brickell Suite Lux and Modern Ocean View 9th Floor

AndrewRating, 5 stars4 days ago
I love this place! bathroom and shower was pretty cool! Lenin was very responsive and helpful with everything! Thank you Lenin!
Guest favorite
A private pool is situated on a terrace, surrounded by light-colored walls and a glass railing. Steps lead down to the water, with tropical plants visible outside, providing a serene and inviting outdoor space.
Condo in Punta Cana
4.9 out of 5 average rating, 134 reviews

Amazing beach Apt with private Pool on the Terrace

BryanRating, 5 stars1 month ago
One of the best Airbnb I’ve ever been to in punta Cana. Very clean the host even stopped by to make sure I was okay with checking in and they helped with finding different excursions and getting you a driver. Definitely was one of the best appreciate y’all.
Top guest favorite
An expansive balcony offers a breathtaking view of the coastline and a serene pool area surrounded by palm trees. Clear blue skies and ocean waves create a tranquil setting, inviting moments of relaxation and enjoyment.
Condo in Juan Dolio
4.94 out of 5 average rating, 155 reviews

Caribbean Comfort

BrendaRating, 5 stars1 week ago
Excellent view, everything as it appears in the images. There is no loss, 👍🏾100 out of 10
Top guest favorite
The living room features large windows offering expansive city views. A stylish, beige tufted couch and two plush orange chairs are arranged on a richly patterned area rug. Modern lighting fixtures enhance the contemporary design, while dark cabinetry provides functional storage.
Condo in San José
4.96 out of 5 average rating, 497 reviews

Architect's Apartment, 21st Floor, Amazing View

Villas Del CaribeRating, 5 stars5 days ago
Great host. Very quick to respond. Clean condo with beautiful views of San Jose city. It’s a must. Jorge is a great guy. Beautiful place.
Superhost
Condo in Luquillo
4.78 out of 5 average rating, 372 reviews

Ocean View-Elevated Luxury Suite(Remodeled)

CarlosRating, 5 stars2 weeks ago
We loved the place, very nice and cozy, beautiful view from the balcony.

Home rentals with a private pool

Guest favorite
An inviting rooftop terrace features a hanging chair and comfortable cushioned seating. A wooden coffee table stands at the center. Lush greenery provides a natural backdrop with trees visible, and the sky showcases soft clouds, creating a serene outdoor atmosphere.
Home in Santo Domingo
4.94 out of 5 average rating, 408 reviews

Gorgeous Colonial House near Cafes and Bars

KemiRating, 5 stars2 weeks ago
We loved staying at Susanne's place! The home is quite big and spacious with high ceilings. The location is excellent and walkable to everywhere in Zona Colonial. The kitchen was well equipped. We appreciated the many fans around the house because it was super hot in DR! The A/Cs in the bedroom were excellent and they do get nice and chilly (always remember to keep all doors and windows closed). The washer/dryer were wonderful to have (although be a little careful as it is right next to the beautiful pool). Susanne was helpful and always ready to help (e.g. offering to bring additional equipment when the wifi wasn't strong in the dining room area). It was also a nice touch to have cleaning service stop by one day. Beds and pillows were super comfortable. We also felt very safe. A little noise on some nights from next door music but nothing too bad. Bathrooms were spacious (hot water always came back even when shower was running for a little while). Highly recommend! Beautiful home!
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, 168 reviews

Soak up the Beachy Vibe at a Vibrant Poolside Paradise

JaneRating, 5 stars2 weeks ago
I really enjoyed my stay at Amy’s place—she was an incredible host! The house was spotless, just like the photos, and located in a quiet, charming neighborhood. It was also super convenient to have a Publix within walking distance for any last-minute needs. It was the perfect spot for our girls' trip and I’d definitely stay here again!
Guest favorite
The image captures a scenic view from a villa's upper deck, showcasing lush greenery below against the vibrant turquoise hues of the ocean. A few lounge chairs with teal cushions are visible, inviting relaxation while enjoying the panoramic coastal vista.
Villa in Christ Church
4.95 out of 5 average rating, 39 reviews

Retreat Style, Sea Views W/ Private Pool & Hot Tub

LudwigRating, 5 stars2 months ago
Quiet, beautiful spot on the south end of the island. Great, private view of the beach and mangroves from sprawling gardens. Occasional monkey visitors. Practical kitchen with needed equipment. Good ac in bedrooms. Giant sliding door for the main room. Strong WiFi in office and most of house and immediate deck (occasionally unstable but think that’s island issue). 15 min to grocery store. Most higher end restaurants and resort beaches on northwest coast 30 min+. Short walk down to beach - rough not swimmable but beautiful. Host was the most helpful we’ve ever had with Airbnb. Helped with all kinds of activity / reservations (for a nominal fee).
Guest favorite
An outdoor patio area is featured with a wooden dining table set for six, accompanied by lounge chairs. A sparkling pool is visible in the background, surrounded by lush greenery and the striking architectural elements of the home, including an aged stone wall.
Villa in Santo Domingo
4.93 out of 5 average rating, 337 reviews

Casa Pantheon Luxury Colonial House

MariaRating, 5 stars2 weeks ago
This house is beautiful. There were two ladies there as housekeepers that were wonderful. Jennifer and Christina. They made breakfast every morning and took great care of us. They were both very kind and made the stay so much better. We also hired the driver that was suggested for the whole week (Rafael). He was amazing and so helpful. Everything was wonderful!
Guest favorite
Bright art-filled space features high ceilings with wooden beams. Colorful paintings adorn the walls, drawing attention to the gallery-like atmosphere. A mix of wicker seating and wooden chairs is arranged around a central table, complemented by a vibrant vase and fresh flowers.
Villa in CARTAGENA
4.87 out of 5 average rating, 154 reviews

Old City Villa - Breakfast & Housekeeping Included

SunnyRating, 5 stars1 week ago
Amazing stay, we had so much fun. It is in heart of the town and close to everything. House attended were so helpful and kind. We would stay again when we come to Cartagena.
Guest favorite
Townhouse in CARTAGENA
4.87 out of 5 average rating, 215 reviews

Walled City Luxurious Townhouse With Private Pool

SamRaatRating, 5 stars1 week ago
"Loved the vintage charm of this place! The host has done an incredible job preserving its character while offering modern conveniences. An unforgettable rooftop experience! We enjoyed the evening skyline, The apartment was absolutely spotless and beautifully decorated. Everything is at walking distance in the old city of cartagena. Our host went above and beyond to make sure we felt at home - communication was seamless with Ivan 👌 Last but not the least - the house help Rosa and her friend took care like a family from breakfast to lunch to dinner with such a delicious food ….. love and hats off to both 🫶
Superhost
A panoramic view from a high-rise balcony captures the expansive coastline meeting the city's skyline. Various buildings, including modern high-rises and low-rise structures, line the streets, with the ocean stretching towards the horizon under a cloudy sky.
Condo in San Juan
4.9 out of 5 average rating, 261 reviews

Condado Beach Views by Cesar 2501

SamuelRating, 5 stars2 weeks ago
Cesar was an excellent host. He was especially friendly and communicated well. I am very happy we stayed here while we went to Puerto Rico. The view was beautiful and the interior was excellent. Will definitely stay here when we do come back!
Guest favorite
A bright and airy cabana offers a blend of indoor and outdoor spaces. Two woven chairs and a round table create a relaxing seating area. A laptop sits on the table, while large glass doors provide views of the heated pool surrounded by greenery.
Guesthouse in West Palm Beach
4.97 out of 5 average rating, 174 reviews

Tropical Cabana with Pool in West Palm Beach

HannahRating, 5 stars1 week ago
We had an absolutely wonderful stay! The house and surrounding space were amazing—beautifully maintained, peaceful, and perfect for a relaxing getaway. The outdoor shower felt like a little oasis, and the pool was fantastic—clean, refreshing, and a great place to unwind. The location was also perfect—conveniently situated near everything we needed, but still quiet and relaxing. Chris was an exceptional host. Despite our very late arrival at 2 a.m., she greeted us warmly and even gave us a tour of the property. Throughout our stay, she was incredibly helpful, offering great recommendations for local activities, restaurants, and directions. We were in town for a wedding, and Chris went above and beyond by kindly taking photos for us before we left for the event—something we truly appreciated. Highly recommend staying here—we’d love to come back!

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