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Holiday 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 favourite
Home in Cartagena
4.9 out of 5 average rating, 101 reviews

Casa Linda

SaraRating, 5 stars1 month ago
Beautiful home excellent location
Guest favourite
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 favourite
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 favourite
Home in Aguadilla
5 out of 5 average rating, 203 reviews

Suite with Private Pool

DanielRating, 5 stars2 weeks ago
5 Stars – A Perfect Stay at Casa Santiago! We stayed at Casa Santiago in Aguadilla from May 22 to 26, 2025, and it was truly an unforgettable experience. From the moment we arrived, we were impressed by the attention to detail and the warm hospitality. The property is absolutely beautiful—clean, well-maintained, and thoughtfully designed with everything you need for a relaxing getaway. The home is perfectly located—close to stunning beaches, great restaurants, and local attractions, yet tucked away enough to enjoy peace and quiet. We especially loved the outdoor space, where we could relax in the evenings and enjoy the island breeze. Our hosts went above and beyond to make sure we were comfortable, offering helpful recommendations and being readily available if we needed anything. It’s clear they genuinely care about their guests’ experience. Casa Santiago exceeded our expectations in every way. We would absolutely stay here again and highly recommend it to anyone visiting the Agua
Guest favourite
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 stars6 days 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 favourite
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 favourite
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.

Apartment rentals with a pool

Superhost
Apartment 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 favourite
Apartment in CARTAGENA
4.93 out of 5 average rating, 180 reviews

De Lujo Frente al Mar-Sector Turistico Bocagrande.

Luther PaulRating, 5 stars5 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
Apartment in Miami
4.86 out of 5 average rating, 155 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
Apartment in Santo Domingo
4.85 out of 5 average rating, 124 reviews

Brickell Suite Lux and Modern Ocean View 9th Floor

AndrewRating, 5 stars3 days ago
I love this place! bathroom and shower was pretty cool! Lenin was very responsive and helpful with everything! Thank you Lenin!
Guest favourite
Apartment 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 favourite
Apartment in Juan Dolio
4.94 out of 5 average rating, 155 reviews

Caribbean Comfort

BrendaRating, 5 stars6 days ago
Excellent view, everything as it appears in the images. There is no loss, 👍🏾100 out of 10
Top guest favourite
Apartment in San José
4.96 out of 5 average rating, 497 reviews

Architect's Apartment, 21st Floor, Amazing View

Villas Del CaribeRating, 5 stars4 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
Apartment 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 favourite
Home in Santo Domingo
4.94 out of 5 average rating, 407 reviews

Gorgeous Colonial House near Cafes and Bars

ErikaRating, 5 stars3 weeks ago
This was my parents’ first international trip, and Susanne’s home made it such a special experience for them. It even gave them the confidence to consider traveling to new places in the future! Since my parents are older, I wanted to find a place that was private, cozy, and comfortable enough for us to enjoy even on rainy days, and this home was perfect. The kitchen allowed us to cook meals together, and we really enjoyed spending time in the pool as well. My parents and I are already planning to return to the DR, and we hope to stay at Susanne’s place again!
Top guest favourite
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 favourite
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 favourite
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 favourite
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 favourite
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
Apartment 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 favourite
Guest house 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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