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

4.96 out of 5 average rating, 136 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.

Apr 21 – 28

$169 per night

Guest favorite

Villa in Sosúa, Dominican Republic

4.86 out of 5 average rating, 113 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 !

Apr 2 – 9

$269 per night

Guest favorite

Villa in La Fortuna, Costa Rica

4.95 out of 5 average rating, 343 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

Dec 29 – Jan 5

$816 per night

Guest favorite

Condo in Miami, Florida

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.

Nov 24 – Dec 1

$458 per night

Guest favorite

Dome in Ponce, Puerto Rico

4.92 out of 5 average rating, 418 reviews

Bubble Puerto Rico Eternal

Tenemos otra Villa disponible con las mismas características - https://www.airbnb.com/h/bubblepuertorico Eternal se une al portfolio de villas de Bubble Puerto Rico. Alojarse en una habitación de burbuja rodeado de la naturaleza jamás había sido tan impresionante. Rodeada entre caña de azúcar, pomarrosa, chinas, café, guineos y una montaña justo en frente es el escenario perfecto mientras disfrutas de la vista al río. Definitivamente una estancia ecológica, mágica, y escondida en las montañas.

Dec 2 – 9

$350 per night

Guest favorite

Apartment in Fitts Village, Barbados

4.94 out of 5 average rating, 108 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.

Sep 1 – 8

$214 per night

Guest favorite

Villa in Guayacanes, Dominican Republic

4.9 out of 5 average rating, 124 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.

Apr 15 – 22

$540 per night

Guest favorite

Villa in Montego Bay, Jamaica

4.93 out of 5 average rating, 149 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 28 – Nov 4

$570 per night

Superhost

Shipping container in Aguada, Puerto Rico

4.88 out of 5 average rating, 217 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.

Feb 15 – 22

$269 per night

Guest favorite

Dome in Orocovis, Puerto Rico

4.93 out of 5 average rating, 161 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.

Feb 13 – 20

$235 per night

Superhost

Treehouse in La Palmera, Costa Rica

4.84 out of 5 average rating, 838 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.

May 12 – 19

$79 per night

Guest favorite

Villa in Santa Teresa beach, Costa Rica

4.96 out of 5 average rating, 107 reviews

Villa Melody

Welcome to Villa Melody ! A beautiful and spacious luxury villa with a stunning ocean and jungle view. Located in an incredible area in the center of Santa Teresa. It is provided with full equipment for your comfort and it’s located just walking distance to the white sand beach, supermarkets, some restaurants and coffee shops.

May 11 – 18

$620 per night