Vacation rentals with a pool in Caribbean Sea

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Caribbean Sea

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, 135 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.

Oct 8 – 15

$169 per night

Guest favorite

Villa in La Fortuna, Costa Rica

4.95 out of 5 average rating, 342 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

Oct 14 – 21

$550 per night

Guest favorite

Dome in Ponce, Puerto Rico

4.92 out of 5 average rating, 417 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

Superhost

Villa in Tres Rios, Costa Rica

4.82 out of 5 average rating, 395 reviews

Award Winning Pura Vida Ecolodge. Very Private

Beautiful & very private eco-luxury retreat near South Pacific Coast (4hr drive with 4WD car) from Juan Santamaria International Airport. Our unique & stunning location offers guests panoramic sea views & hangs dramatically over the jungle canopy. Romantic getaway, nature lovers & adrenalin junkies paradise! We’re proud to be a 1% For the Planet Member, giving 1% of our annual revenue back to local environmental nonprofits working on conservation projects for both our people and our planet.

Mar 19 – 26

$320 per night

Guest favorite

Condo in Cancún, Mexico

4.93 out of 5 average rating, 331 reviews

The Quarry, Beachfront sub penthouse 150m to clubs

From the moment you enter the property you will realize why you came to Cancun; the powder soft white sand beach, and the most beautiful turquoise water. Because, that is all you can see from the 180° panoramic views the apartment offers. No detail was spared. Over 2 years remodelling this one of a kind property. Only 150m to all the nightlife, 2 large pools, a restaurant & beach club in the building. A Fusion of exotic wood furniture and imported marble have this place unmatched in Cancun.

Oct 30 – Nov 6

$404 per night

Guest favorite

Condo in Montego Bay, Jamaica

4.92 out of 5 average rating, 367 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.

Feb 28 – Mar 7

$195 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.

May 29 – Jun 5

$540 per night

Guest favorite

Villa in Montego Bay, Jamaica

4.93 out of 5 average rating, 148 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 6 – 13

$563 per night

Superhost

Shipping container in Aguada, Puerto Rico

4.88 out of 5 average rating, 216 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.

Jul 8 – 15

$269 per night

Superhost

Cottage in Valladolid, Mexico

4.85 out of 5 average rating, 396 reviews

Jungle refuge with private plunge pool

Named one of Mexico's best Airbnb's by Condé Nast and featured in publications such as Architectural Digest, Glocal Magazine & Archdaily . Casita Jabín is an award-winning relaxing refuge located in the Yucatán jungle, 10 minutes away from the colonial town of Valladolid and just across the street from Cenote Suytún. Featuring contemporary Mexican architecture, clean design and a private plunge pool, it’s the perfect place to rest and unplug.

Feb 3 – 10

$139 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 9 – 16

$235 per night

Superhost

Home in San Isidro de El General, Costa Rica

4.85 out of 5 average rating, 266 reviews

Casa Luz

Located in Costa Rica’s Southern Pacific Zone, La Luz sits atop a mountain overlooking the stunning Baru River Valley. The property sits on 12 acres in the gated community of Valle de los Caballos- surrounded by sweeping vista views, bamboo lined drives, waterfalls, and a jungle that‘s home to the wildest flora and fauna of the area.

Nov 24 – Dec 1

$135 per night