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 28 – Oct 5

G$40,489 GYD per night

Superhost

Dome in Ponce, Puerto Rico

4.93 out of 5 average rating, 545 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

Aug 15 – 22

G$59,561 GYD per night

Guest favorite

Villa in Sosúa, Dominican Republic

4.86 out of 5 average rating, 112 reviews

836 CASALINDA

Over 4000 sq. ft. !!! This Place screams Party !! 65in TV in living room , outside bar 65 in tv , Barbecue pit , board game floaties for the pool ! I did this place first class please enjoy it like I do , no smoking inside we like to keep the place smelling good by all means smoke outside with a nice cold beer enjoying the pool watching sports on the outside bar , enjoy life! Just installed Hue lighting Sonos throughout the house and pool area. have a huge blue tooth speaker and a wine chiller !

Dec 31 – Jan 7

G$64,462 GYD per night

Guest favorite

Villa in La Fortuna, Costa Rica

4.96 out of 5 average rating, 339 reviews

House of Views w/ King Bed + Volcano View

This exclusive and stylish property features gorgeous views of the volcano that can be enjoyed from anywhere in the house. Take a moment to breathe fresh air from the terrace and connect with the nature surrounding you, all this while you savor a warm cup of Costa Rica’s best coffee. After a day of exploring and hiking to the famous waterfall come back to unwind at the jetted pool and reload for another day of fun. Discover La Fortuna like a local while enjoying of privacy, comfort and luxury

Feb 12 – 19

G$145,580 GYD per night

Guest favorite

Condo in Miami, Florida, US

4.9 out of 5 average rating, 151 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.

Sep 13 – 20

G$72,051 GYD per night

Guest favorite

Apartment in Fitts Village, Barbados

4.93 out of 5 average rating, 107 reviews

La Porta Della Casa - Sunset Platinum West Coast

La Porta Della Casa is a modern, contemporary accommodation located on the platinum coast of Barbados, within walking distance to the nearest beach and close to great restaurants such as The Tides, The Cliff, Cin Cin By The Sea, Nishi and Fusion, to name a few. 7 minutes' drive from the famous Limegrove Mall in Holetown with duty-free shopping and supermarkets . On Sunday night, 2nd street comes alive with their street party. 7 minutes' drive from the city of Bridgetown with more duty-free.

Apr 8 – 15

G$63,401 GYD 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.

Feb 15 – 22

G$128,815 GYD per night

Superhost

Villa in Soufriere, St. Lucia

4.86 out of 5 average rating, 165 reviews

Villa Piton Caribbean Castle

Certified to host on St Lucia government website at stlucia.org. Super private and provides a secure and isolated retreat far from any crowds! We provide cooking service for breakfast lunch or dinner for an extra fee prepaid through Airbnb prior to your arrival. We incorporate heightened cleaning procedures and trained staff. Built by John DiPol, designer of the world-famous Ladera resort, Villa Piton elaborates on the open-aired concept providing breathtaking views everywhere!

Sep 1 – 8

G$110,604 GYD per night

Guest favorite

Farm stay in Bonao, Dominican Republic

5.0 out of 5 average rating, 230 reviews

Hacienda del Río, Bonao - Casa doña Celia Eco Farm

Ideal for a group of friends and/or family, capacity for 6 people, with everything you need to spend a quiet and family holiday. Safe place, staffed for 24/7 assistance. Convenient location; close to the capital and Santiago. Ideal for nature lovers, hikers, cyclists, and all those looking for greenery, and peace. We include programs of activities with the animals of our farm. Routes available for trails, enduro and cycling. A real paradise!

Oct 31 – Nov 7

G$36,748 GYD per night

Guest favorite

Dome in Orocovis, Puerto Rico

4.93 out of 5 average rating, 158 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

G$58,181 GYD per night

Guest favorite

Cottage in Monteverde, Costa Rica

4.97 out of 5 average rating, 156 reviews

Villa 3 - Heated private pool and amazing sunsets

Relax and enjoy the best sunsets at Villa 3, this new house is fully equiped for your perfect getaway. Fully furnished with everything you need for your holidays. Connect with nature and enjoy the amazing views that surround the house. You will hear birds chanting every day during the sunrise and sunset. We are located on privileged spot that has an amazing view of the gulf of Nicoya.

Sep 14 – 21

G$91,974 GYD per night

Superhost

Treehouse in La Palmera, Costa Rica

4.84 out of 5 average rating, 836 reviews

Rainforest Tree House with Hot Springs

No children under 7 years of age for safety reasons. The Tree House is hand-crafted, one of 3 casitas and 3 treehouses at the Bio Thermales natural resort organically integrated into our 35 acre rainforest. Guests enjoy free access, from 9 am to 10 pm to the 15 natural hot and cool springs pools of various temperatures and rainforest trails.

Oct 24 – 31

G$18,892 GYD per night