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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
4.74 out of 5 average rating, 42 reviews

Home in Oakland park with pool

DelmarriRating, 5 stars4 months ago
Easily accessible yet tucked away, offering just the right level of privacy. It was so peaceful and quiet, perfect for relaxation. The setting made it feel like a true getaway.
Guest favorite
Home in Sarasota
4.96 out of 5 average rating, 57 reviews

2223 Doud Street, Sarasota, FL

JoanRating, 5 stars3 months ago
Great location for accessing a wide range of local services & amenities. Very comfortable home which suited our family very well. The warm pool was great. Lovely & quiet despite being just off a main road. We had a great holiday in Sarasota despite the recent hurricanes. Thanks!!
Guest favorite
Home in Bonita Springs
4.93 out of 5 average rating, 140 reviews

Pool house near Hyatt Regency Coconut Point

KerryRating, 5 stars7 months ago
Thank you, Henrieta! We had a great stay & definitely plan to return. Our host is welcoming, friendly & provided us with everything we could have needed or wanted.
Guest favorite
Home in Cape Coral
4.86 out of 5 average rating, 86 reviews

Comfy Cape house 4 beds/2baths/heated pool/Jacuzzi

HerbertRating, 5 stars1 month ago
Very nice cozy home well setup with everything you need.
Guest favorite
Home in San Juan
4.92 out of 5 average rating, 36 reviews

Pool/3BR 11 min SJU airprt/beach

AzuomaRating, 5 stars1 week ago
If you’re looking for a get away definitely consider booking this place great experience wouldn’t ask for anything more.
Superhost
Home in Lehigh Acres
4.83 out of 5 average rating, 129 reviews

LIVING in PARADISE 🌴 ⛱️ 😎

SherriRating, 5 stars2 weeks ago
Dario’s place was nice. Very quiet neighborhood with nice neighbors. During the week we had a couple issues, one with the pool heater not turned on and one with the tv, but both times Dario was super quick to respond and had someone out right away to fix any issues! He is a super nervous very guy!!
Superhost
Home in Oranjestad
4.92 out of 5 average rating, 144 reviews

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

AllanRating, 5 stars1 week ago
Me and my family had an amazing stay. Great location and very comfortable spacious house. Not too far from the beach driving distance. I would recommend to anyone
Superhost
Home in Cape Coral
4.84 out of 5 average rating, 31 reviews

Tropical House with Pool

TyresaRating, 5 stars2 months ago
My stay was amazing.. This was my first Air bnb and I definitely would recommend. The host was very easy going and proactive with communication. I have no complaints.

Condo rentals with a pool

Guest favorite
Condo in Fort Pierce
4.93 out of 5 average rating, 107 reviews

Modern BEACH Condo in Peaceful Hutchinson Island

ChristinaRating, 5 stars1 month ago
I loved the condo! I was able to work and enjoy Fort Pierce. The people were kind and the gated community felt safe and welcoming.
Guest favorite
Condo in Rockley
4.92 out of 5 average rating, 143 reviews

Spacious 2 Bedroom Luxury Condo.

GeorgeRating, 5 stars2 weeks ago
Our family has stayed at Toby's place multiple times over the years..... never disappoints, and overall good value.
Guest favorite
Condo in Jacó
4.84 out of 5 average rating, 79 reviews

3 BDR Condo w/pool, walk to beach & restaurants

KarinaRating, 5 stars4 days ago
The place, the villa, everything inside it was excellent, the location, the host, my family really enjoy, accessible for people with disabilities and children
Guest favorite
Condo in Miami
4.88 out of 5 average rating, 17 reviews

Modern Spacious 2 Bed In Aventura/ FREE Parking

JarredRating, 5 stars1 month ago
Dmitry was a very responsive host. Place was consistent with the photos.
Superhost
Condo in Pompano Beach
4.85 out of 5 average rating, 272 reviews

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

AlexRating, 5 stars1 week ago
Marilyn’s place was great. Check in was super easy condo was very nice and perfectly clean. 5 minute walk from the beach. Pool was great and has a light at night. Stayed with our 3 kids they loved the pool and beach. Condo even had beach toys and wagon to use. Marilyn was very fast answering any questions we had and was very helpful. Would stay again!
Superhost
Condo in San Andrés
4.76 out of 5 average rating, 41 reviews

Dreamy pool side condo

LuisRating, 5 stars1 month ago
I will say this: this is one of the best hosts I’ve ever met. Diana is just something special. Would book with her 1000 times more
Guest favorite
Condo in Sarasota
4.97 out of 5 average rating, 61 reviews

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

JulieRating, 5 stars1 month 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 Kingston
4.97 out of 5 average rating, 58 reviews

Quiet , pool, gated,security

JohnniceRating, 5 stars4 days ago
I recently had the pleasure of staying at this airbnb in New Kingston, Jamaica, and it was an incredible experience! From the moment I arrived, I was greeted with warm hospitality and a welcoming atmosphere. The location is perfect, situated right in the heart of New Kingston, making it convenient to explore the vibrant city and its many attractions. The accommodations were top-notch, offering a perfect blend of comfort and luxury. My room was spacious, impeccably clean, and beautifully decorated with modern furnishings. The bed was incredibly comfortable, ensuring a restful night's sleep after a day of sightseeing. I also appreciated the thoughtful amenities provided, such as complimentary Wi-Fi, a well-stocked minibar, and a flat-screen TV with a wide range of channels. Overall, The host Nicolas exceeded all my expectations. The combination of excellent service, prime location, and luxurious accommodations made my stay unforgettable. I can’t wait to return.

Home rentals with a private pool

Guest favorite
Home in Santo Domingo
4.94 out of 5 average rating, 392 reviews

Gorgeous Colonial House near Cafes and Bars

SandraRating, 5 stars2 weeks ago
Big, clean and nicely decorated house. It's located in a very centric area. walking distance to restaurants and bars.
Guest favorite
Home in West Palm Beach
4.96 out of 5 average rating, 159 reviews

Soak up the Beachy Vibe at a Vibrant Poolside Paradise

KristalRating, 5 stars2 weeks ago
Amy’s place was exactly as described, private and a perfect fit for my family of 4. Thank you for a wonderful trip Amy!
Guest favorite
Villa in Santo Domingo
4.93 out of 5 average rating, 323 reviews

Casa Pantheon Luxury Colonial House

NelsonRating, 5 stars2 weeks ago
This place is beautiful and amazing beyond expectations! The host and house staff such as Jennifer are beautiful people. The aura is vibrant and the decor is such a refresher to adore while relaxing. This place will have you certainly feeling energetic and comfortable.
Guest favorite
Villa in Cartagena
4.87 out of 5 average rating, 149 reviews

Old City Villa - Breakfast & Housekeeping Included

MarinaRating, 5 stars2 days ago
I had an incredible stay at this beautiful villa in Cartagena! The location is perfect! centrally located, yet in a very peaceful and accessible area. The safety of the place was impressive! The villa itself was stunning, with a charming Spanish feel that really added to the ambiance of our stay. The aesthetic was both inviting and relaxing, offering plenty of space for our group of 10 to comfortably spread out. The rooms were spacious, and we never felt cramped. Sebastian was very responsive and accommodating. big shoutout to the ANNIE who kept everything spotless and made sure we had everything we needed. She was incredibly helpful and friendly. The night guard LUIS was also fantastic, always available and ready to assist us. If I had to mention a minor downside, it would be the lack of mirrors in some of the rooms and the need for a few more electrical plugs to accommodate all of our devices. However, these were small things that didnt affect our trip. Highly recommend this place
Superhost
Bungalow in Punta Cana
4.79 out of 5 average rating, 311 reviews

Sink into the Pool of a Wonderful Bungalow

JoshuaRating, 5 stars1 month ago
I definitely enjoyed my stay here. The views and cleanliness were top tier. VERY peaceful/safe neighborhood. Friendly neighbors. Good communication with host about locating the airbnb. Receptive to feedback. Nice restaurants nearby and eateries on nearby resorts. I had to take trips a little further out to do activities/popular attractions BUT I love that this location was out the way and very peaceful/very quiet neighborhood. I definitely recommend and I would definitely return.
Guest favorite
Townhouse in Cartagena
4.87 out of 5 average rating, 203 reviews

Walled City Luxurious Townhouse With Private Pool

MarjorieRating, 5 stars3 weeks ago
What a great experience we had in Cartagena at Iván's place. We enjoyed all the amenities the condo and the complex had to offer. Great sauna, well equipped gym, massage service in the room, made our stay even better, this things are important to us. Woke up to a delicious breakfast, explored Cartagena and came back to the condo to cool off in the pool or rooftop jacuzzi... Trust me when I tell you, you don't need heater for the jacuzzi. Cartagena is in the 90s F. We had lunch prepared by Rosa and Katia and explore more of Cartagena after that. The condo is located in the perfect spot! A short block away from everything but at the same time not in the middle of the hustle and bustle of the city. We enjoy our nights relaxing in the rooftop and watching movies on the very comfortable couch!
Guest favorite
Villa in Tamarindo
4.96 out of 5 average rating, 25 reviews

Tropical Retreat - Private Pool, Steps to Beach

JacobRating, 5 stars1 month ago
Amazing house and location!
Guest favorite
Condo in San Juan
4.9 out of 5 average rating, 249 reviews

Condado Beach Vistas by Cesar 2501

PaulinaRating, 5 stars1 day ago
We had a wonderful stay at Cesar’s place! The location is excellent—just a short drive from the airport and Old San Juan, with easy access to restaurants, bars, and beaches. The view of the beach and city from the balcony is absolutely spectacular. The space was clean and well-equipped with everything we needed. However, there are a few minor drawbacks to note. The unit is not soundproof, so we were occasionally woken up early by construction noise and sirens. The fridge had a distinct odor, and parking can be a bit tricky if you have a larger car due to the surrounding pillars. That said, we highly recommend this stay for anyone visiting San Juan. Cesar is a fantastic and friendly host, making the experience even better!

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