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Holiday 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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Top guest favourite
A charming cabin crafted from natural materials is positioned atop a wooden structure. A thatched roof provides shade, while large glass doors invite light. A pool is visible in the foreground, reflecting the blue sky and surrounding greenery.
Cabin in Isabela

Casa Lola PR

In Casa Lola, nature is the protagonist of a hidden spot surrounded by mountains in Isabela. Unique views and a perfect place to disconnect and reconnect with your couple…. Come and enjoy our beautiful cabin on top of the mountain, completely private and experience the best nature environment. Fully equipped kitchen, indoor and outdoor showers, loft room with amazing sunrise and sunset views, infinity pool, sun chairs and relaxing hammock. A place that invites you to come again…..just enjoy.

LocationValueLong stay

4.99 out of 5 average rating, 298 reviews
Top guest favourite
A modern oceanfront chalet is visible, featuring a pool surrounded by a patio. White lounge chairs and a wooden table are arranged nearby. The structure showcases a spacious design with large windows and a colorful mural. Lush greenery frames the area under a bright blue sky.
Chalet in Puerto Nuevo

“CASA ROARK” is a one-of-a-kind oceanfront chalet.

“CASA ROARK” IS A ONE-OF-A-KIND OCEANFRONT CHALET WITH VIEWS THAT CAN EASILY BE AMONG THE MOST BEAUTIFUL WORLDWIDE. IT IS ONLY A FEW STEPS FROM THE BEACH. THE RECENTLY REMODELED CHALET HAS 4 BEDROOMS, ALL WITH A/C AND 65"TVS; THE 1st MASTER ROOM HAS A KING-SIZE BED AND A TWIN SOFA BED, THE 2nd MASTER BEDROOM HAS A QUEEN SIZE BED, THE 3rd HAS 2 BUNK BEDS AND THE 4th ROOM HAS TWO TWIN SIZE BEDS. YOU HAVE A BEAUTIFUL HEATED POOL OVERLOOKING THE OCEAN. POOL USE IS ONLY FOR OUR GUESTS.

FamilyLocationCleanliness

4.95 out of 5 average rating, 308 reviews
Guest favourite
Apartment in Punta Cana

Exclusive Studio w/ Balcony & King Bed - Cap Cana

Daydreaming about escaping to the beach during your next vacation? Look no further! Our beachfront studio in front of Marina Cap Cana is a beautiful spot to get serious about relaxation. Check out the highlights of our space below: ➢ 1 Spacious Bedroom/1 Bathroom with Shower/Bathtub ➢ Private Beach Access ➢ Beach/Ocean View with balcony ➢ Fully Equipped Kitchenette ➢ Swimming Pool ➢ Free Wifi ➢ 24/7 Security ➢ Portable Crib provided upon request ➢ Bath and beach towels provided

FamilyValueParking

4.96 out of 5 average rating, 126 reviews
Luxe
A spacious terrace area is shown, featuring comfortable lounge chairs and a shaded umbrella. Lush greenery surrounds the space, creating a relaxed atmosphere. Light-colored furniture is complemented by woven details, and a refreshing pool is visible in the background, enhancing the outdoor experience.
Villa in Centro

Casa O Cochera Luxury Boutique House

Welcome to Casa O Cochera! Immerse yourself in luxury at this new 4-story haven in San Diego's enchanting Walled City. Designed by the renowned architect Vladimir Caballero, our house accommodates 8 guests with utmost comfort. Enjoy complimentary delicious breakfast, airport transfer and attentive housekeepers. Elevate your stay with optional catering, entertainment, and exciting tours. Your unforgettable getaway awaits! Book now and create beautiful memories at Casa O Cochera.

ValueFamilyNearby

4.93 out of 5 average rating, 127 reviews
Luxe
An outdoor area features a rectangular swimming pool with clear water, surrounded by a deck area with lounge chairs. A striped umbrella provides shade, while views of the ocean and sandy beach create a serene backdrop. Lush greenery frames the space, enhancing the coastal ambiance.
Villa in Providenciales

Villa DelEvan 4A / 1-bedrm Beach front villa

Centrally located on the Grace Bay Beach, a perfect place for luxury, rest & tasting the best island cuisine. Close to everything you need for a great vacation: Walking dist. from 4 restaurants - Mango Reef, Shark Bite, Baci & Simone’s. 10 min drive to the famous island Fish Fry, 15 min drive to the Airport, 5 min drive to the supermarket. Gated property, private parking, 24hr security. Boating/fishing/sightseeing/wind surfing & more. Water sports pick-up on property.

FamilyValueLong stay

4.99 out of 5 average rating, 144 reviews
Top guest favourite
An infinity pool cascades gently into a lower plunge pool, surrounded by lush greenery. The sparkling water reflects the sunlight, while the shimmering sea is visible in the background, enhancing the serene outdoor setting.
Villa in Treasure Beach

Sanguine Villa Treasure Beach 1-2-3 bed option

Sanguine's spacious fully staffed beachfront Villa with an infinity pool is located in Treasure Beach on Jamaica's South Coast. Treasure Beach is where one comes to get away from the hustle and bustle of everyday life and happily ensconce themselves in our laid-back community. Latoya will be here to ensure that you have a holiday of memorable meals, you sit back and relax while we do the grocery shopping and look after you. Message me re airport and transport options

ValueLocationSleep quality

5.0 out of 5 average rating, 106 reviews
Top guest favourite
A serene outdoor living space features comfortable seating arranged around a low table, with panoramic views of a sunset over lush greenery. An infinity pool reflects the vibrant colors of the sky, framed by large glass doors that open to the natural surroundings.
Home in Monte Verde

Luxury villa & Infinity Pool

Immerse yourself in tranquility and natural beauty with this spectacular house in the middle of the forest, designed to offer you a unique experience of luxury and relaxation. This property combines modern elegance with the charm of nature. Wake up to the sounds of the forest and enjoy the peace that only this natural setting can provide. The house offers total privacy, but is located in the heart of Monteverde, a short drive away from local restaurants and shops.

LocationValueComfort

4.97 out of 5 average rating, 113 reviews
Top guest favourite
Villa in La Fortuna

Villa Mano de Tigre, A Volcano in your Garden!

The Holiday Villa with the closest and most SPECTACULAR view of Arenal Volcano Beautiful natural landscapes, a cool and private area, away from mass tourism. Safe gated property. 10 minutes to downtown La Fortuna. Fully equipped. Private hot tub. Campfire area. Optic fiber high speed Wi-Fi Located 1.5 kilometers from the main road atop a private hill where you will be surrounded by flora and fauna. Base rate for 2 people. Vehicle is recommended.

ValueFamilyAccuracy

4.98 out of 5 average rating, 216 reviews
Top guest favourite
An outdoor terrace features comfortable white lounge furniture arranged around a coffee table. Sun loungers are positioned beside a private infinity pool, overlooking the ocean and distant boats. The scene is framed by tropical plants and a clear blue sky, enhancing the serene coastal environment.
Loft in Marigot

Sea Loft, Breathtaking View – Private Pool

* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with lounge chairs, garden furniture, outdoor table and BBQ * Office area * 100 Mbps Wi-Fi * TV with thousands of channels from around the world * 250 m walk to Fort Louis de Marigot Marina * 5 min walk to Marigot city center with its restaurants, boutiques and other shops * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

ValueFamilyWalkability

5.0 out of 5 average rating, 202 reviews
Top guest favourite
The image captures a serene oceanfront setting, featuring a magnesium pool that reflects the warm sunset. Lush greenery borders the pool area, with palm trees framing the scene, creating a peaceful atmosphere. The calm sea is visible beyond the pool's edge.
Villa in St. Willibrordus

Villa Yazmin - Ocean Front Villa

Follow us @villa_yazmin_curacao Experience refined luxury with stunning ocean views. A beautiful piano for serene moments, a magnesium pool gentle on body and skin, and elegant bedrooms each with a private bathroom. A fully equipped kitchen with cappuccino machine and Quooker. Car rental, early check in and late check out available upon request. Please contact Mary in advance for personalized arrangements. Warm greetings, Villa Yazmin Mary

LocationValueSleep quality

4.91 out of 5 average rating, 133 reviews
Top guest favourite
Guest house in Venecia

Treetop cabin - hot tub, pool & private rainforest

An unique and modern treetop cabin hidden in 10 acres of private primary rainforest, in a peaceful small town of rural Costa Rica, with La Fortuna, Bajos del Toro and Sarapiquí all within reach. Soak in your own private heated hot tub on the balcony while the forest does the talking, waterfall sounds included. Full kitchen, rain shower looking at the treetops, river, trails and two pools with natural spring water. Local owned ✌️🇨🇷

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 113 reviews
Top guest favourite
Home in Venecia

La Ceiba, Villa w/Infinity Pool on a Dairy Farm

Escape to La Ceiba, a private retreat on our family dairy farm surrounded by lush pastures, cows and mountain views. Relax by the infinity pool, enjoy beautiful sunrises and sunsets, and gather in the spacious open-air living and dining areas. With 3 bedrooms, 4 queen beds and space for up to 8 guests, it’s ideally located between Bajos del Toro and La Fortuna. Private chef service available.

ValueLocationWifi

4.97 out of 5 average rating, 224 reviews

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