Vacation rentals with a pool in Caribbean

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Caribbean

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in San Cayetano de Venecia, Costa Rica

4.95 out of 5 average rating, 133 reviews

Quinta La Ceiba Modern Home with Pool in DairyFarm

A contemporary roomy vacation home situated in a dairy farm. Embrace serenity, unwind in a tranquil haven surrounded by cows grazing in lush green fields. It's a birdwatcher's paradise too. This is an ideal escape to disconnect and reconnect with nature. Dine and lounge outdoors make the most of the property's features. Our in-house travel concierge will be glad to arrange tours and activities for you at no additional cost. Consider our private chef service for an even more memorable experience.

Sep 17 – 24

ﺩ.ﺇ713 per night

Guest favorite

Townhouse in Ocho Rios, Jamaica

4.93 out of 5 average rating, 122 reviews

Beautiful vacation home in the heart of Ocho Rios

24/7 gated security country mist community. Ideally situated 5 min away from the City Centre in hills of Ocho Rios nestled amidst lush tropical greenery and stone throw away from famous attractions such as Dunn's River Falls, Dolphin Cove, Margaritaville, Mystic Mountain Rainforest, Konoko Falls and Park and many fine restaurants. We offer a well-appointed luxury retreat including fast WIFI, swimming pool, fully air conditioned rooms, large screen TVs in all room for your comfort and convenience

Nov 27 – Dec 4

ﺩ.ﺇ522 per night

Superhost

Dome in Ponce, Puerto Rico

4.93 out of 5 average rating, 543 reviews

Bubble Puerto Rico

Tenemos otra Villa disponible con las mismas características - https://www.airbnb.com/h/bubblepuertoricoeternal ¡Experimenta por primera vez en PR quedarte en una habitación de burbuja! Bubble PR es una estancia ecológica, mágica, escondida en las montañas de Ponce, PR. A 18 minutos de la Ciudad, podrás sumergirte en una experiencia única, romántica, para parejas o viajeros solos, rodeada de naturaleza, abundante en flora, fauna y situados en la orilla de uno de los ríos mas abundante de Ponce

Jul 17 – 24

ﺩ.ﺇ1,049 per night

Guest favorite

Condo in Miami, Florida, US

4.9 out of 5 average rating, 147 reviews

ICON 2B/2B Skyline Free Pool, Spa, HotTub

INSTA READY, This unit provides over 1,350SqFt of breathtaking ocean and city views with Two Bedrooms and Two Bathrooms. Located within the luxurious Icon building. The Icon is a 5 star condominium. It is located inside the heart of Downtown Miami/ Brickell. It includes the same amenities as the W Hotel, such as free access to spa, pool, hot tub, and 4 restaurants, including Cipriani. The apartment comes with three flat screen TVs, HighSpeed WiFi, and toiletries. As well as four separate beds.

Oct 31 – Nov 7

ﺩ.ﺇ1,694 per night

Guest favorite

Condo in Montego Bay, Jamaica

4.92 out of 5 average rating, 366 reviews

Jus' Beachy! Luxury Apt in a B/front Gated Cmnty.

This new beach theme apartment is located in 22 Freeport – A gated community in Freeport Montego Bay. 22 Freeport is a beach front complex on a Marina that features 24 hour security, a gym, infinity edge pool and playground; whilst the unit on the ground floor opens onto a cozy back yard space that flows into an open green space. Be sure to check out my other units in this community on my profile if your dates are not available or if you would like to book them all for your large group.

Dec 17 – 24

ﺩ.ﺇ822 per night

Guest favorite

Villa in Guayacanes, Dominican Republic

4.9 out of 5 average rating, 123 reviews

Guayacanes Village- Front beach house

Lujosa casa frente al mar ubicada en el municipio de Guayacanes, equipada con todo lo necesario para una estadia placentera. La casa se encuentra a 15 minutos del aeropuerto y 45 minutos de la ciudad de Santo Domingo. Esta es una propiedad para disfrutar con la familia y amigos cercanos. No permitimos fiestas, bodas y eventos de muchas personas. Tampoco permitimos la entrada de personas extrañas como strippers y prostitutas. El turismo sexual no esta permitido en nuestra propiedad.

Mar 2 – 9

ﺩ.ﺇ2,268 per night

Guest favorite

Home in Sarasota, Florida, US

4.94 out of 5 average rating, 146 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 bedrooms & baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown and more. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack.

Sep 15 – 22

ﺩ.ﺇ1,693 per night

Guest favorite

Villa in Montego Bay, Jamaica

4.93 out of 5 average rating, 147 reviews

VIBES COVE enjoy your stay while getting pampered

FREE Arrival meal , the first day you arrive to vibes cove you’ll receive a complementary arrival meal by our personal chef on the property. Vibes coves villa is super Spacious and private enjoy your vacation by getting pampered. This property comes with a personal chef , Butler, and housekeeper. Enjoy V.I.P services your entire stay. Property staff stays in their helpers quarters ( not apart of the property ) only those listed on the Airbnb is allowed at the property.

Oct 13 – 20

ﺩ.ﺇ2,428 per night

Guest favorite

Apartment in Miami, Florida, US

4.89 out of 5 average rating, 678 reviews

Luxury ICON Brickell Condo @47th Floor / POOL

This Unique and Deluxe 5-star Condo, Fully Equipped and located in the same building of the famous W Hotel, Icon Brickell, at 47th-floor with the biggest SWIMMING POOL in town. We are located on the mouth of Miami river on the sea, with amazing views of the sunrise in the morning and sunsets in the dusk. Steps from City Centre Mall, downtown, restaurants, cafés, and nightclubs. Five to six miles from Design District & South Beach. THIS IS THE PLACE TO STAY!

Jun 1 – 8

ﺩ.ﺇ862 per night

Superhost

Shipping container in Aguada, Puerto Rico

4.88 out of 5 average rating, 215 reviews

Visum Luxury Container House

Experience the beauty of the west side of Puerto Rico has to offer. A shipping container house full of glam and luxury that will enhance an unforgettable stay. A two bedroom and two bathroom house full of amenities such as infinity pool, a fully equipped kitchen, 100% powered house with renewable energy and outstanding views from every corner of the house. From the first sip of coffee until the moment to go to bed you will experience “Visum” at it’s best.

Nov 26 – Dec 3

ﺩ.ﺇ1,218 per night

Guest favorite

Dome in Orocovis, Puerto Rico

4.95 out of 5 average rating, 157 reviews

The LM1 Domescape

Acompáñanos a un lugar mágico e inolvidable en los interiores de nuestra isla, Orocovis PR. Disfruta del encantador entorno de este Domo y todo de lo que ha de ofrecer. A solo minutos de lugares turísticos como lo es Toro Verde, Toro Negro y ciertos rios en donde puedes dar un chapuzon! Además estamos a solo minutos de ciertos restaurantes donde puedes tener un brunch, almuerzo, cena o simplemente pasar a darse un trago o picadera.

Aug 3 – 10

ﺩ.ﺇ1,025 per night

Superhost

Home in CR, Costa Rica

4.85 out of 5 average rating, 143 reviews

Casa Pura Vida

This is our newest listing , Casa Pura Vida! A perfect place to work, relax, surf and have fun. It’s conveniently located in the growing luscious neighborhood of Playa Negra Heights. Walking distance to the beach , 2.5KM to Puerto Viejo town . This home is nestled in a quiet forest, surrounded by beautiful houses , you’d say is the most exclusive area of Playa Negra . wifi pool close to all amenities

Nov 16 – 23

ﺩ.ﺇ674 per night