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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 wide view captures the vibrant turquoise ocean meeting the blue sky, with scattered clouds above. Lush greenery lines the sandy beach, leading towards a modern beachfront villa on the left, blending with the tropical landscape.
Home in Governor's Harbour
4.91 out of 5 average rating, 171 reviews

Cayo Loco Villa 1 Pinksand Deserted Beach 2 Adults

S2E2 NETFLIX "WORLD'S MOST AMAZING VACATION RENTALS"! Beachfront villa right on deserted secluded pink sand beach! Watch dolphins with your coffee/coconut water/tarts! Beach toys included! Eleuthera means 'freedom'! Tranquil authentic tropical island paradise fusing eco design w/comfort! 1 of 3 brightly colored villas! Beach stroll to dining/bar/pool! Fish/surf/boat/dive/kayak/paddle board/relax! Unspoiled pristine oasis! 1 bed 1-1/2 bath 2 ADULTS ONLY! NO SMOKING/KIDS/LOUD MUSIC/VISITORS/FIRES!

Top guest favourite
The exterior of the cottage is framed by vibrant tropical plants and flowering shrubs, showcasing a blend of lush greenery and colorful blooms. The white structure features a sloping roof, supported by two elegant columns at the entrance.
Cottage in West Bay
4.99 out of 5 average rating, 351 reviews

Luxury Cottage, 1bd/1ba steps to Pool+7 Mile Beach

Our Queen Cottages are part of the Botanica collection of award winning island style cottages. This unit has a private outdoor dining and garden shower. At Botanica, our focus is on casual luxury, dreamy details and high end amenities. Property highlights includes a resort style pool with heated spa set in a tropical oasis. We also offer a complimentary shuttle in our vintage Land Rover Defender to nearby beaches. Be sure to check out our other listings under my profile. Non Smoking Complex

Top guest favourite
A private pool is surrounded by vibrant greenery and palm trees, providing a tropical ambiance. Two wooden chairs with soft cushions sit at a small table, with clear water glistening in the pool. The ocean can be seen in the background, adding to the serene setting.
Home in Willemstad
4.95 out of 5 average rating, 165 reviews

Private Oceanfront luxurious city villa with pool

Welcome to a beautiful Paradise in Pietermaai District. This 300yr old estate has been restored to perfection after having suffered severe neglect. The unique design style and decoration has been done with love for architecture. The villa can be found in Pietermaai District also known as the ‘Soho of Curacao’’, where monuments meet modern times. With an oceanfront stunning view + private pool, the villa is ideal to get away from it all whilst still be close to great restaurants and live music.

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
4.99 out of 5 average rating, 227 reviews

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.

Top guest favourite
An infinity pool is featured with views of surrounding mountains and lush greenery. Sunlight reflects off the water's surface, creating a serene atmosphere. Chaise lounges are positioned nearby, offering a comfortable space to relax and enjoy the picturesque landscape.
Tiny home in Caonillas Arriba
5 out of 5 average rating, 110 reviews

Sol y Luna Mountain Retreat Hacienda

Enjoy the lovely setting of this romantic spot in nature and discover the serenity in our cozy farmhouse. This private villa wraps you in a lovely and peaceful environment with majestic mountains all around. The house is fully equipped for your convenience. It is ideal for couples in need of a nice getaway or just reconnect with yourself and nature. It is on a gorgeous tropical private 3 acre estate with private pool. Located in Villalba, Puerto Rico, just 50 minutes from Ponce's Airport.

Top guest favourite
A unique bedroom features natural wooden walls and flooring, with a spacious bed positioned on a raised platform. Large windows offer a view of the surrounding trees, while soft lighting highlights the room’s architectural design.
Guest house in Los Mesen
5 out of 5 average rating, 209 reviews

Unique & peaceful forest cabin with pool & trails

Retreat to the rainforest in a cosy, secure and modern luxury cabin, built to help you connect with nature and yourself. Enjoy your stay with a fully equipped kitchen, an amazing bathroom with a custom shower/hot tub and a one of a kind bedroom design. Explore the private trails of the property with 10 acres of primary rainforest with toucans, lapas, humming birds, butterflies and other fauna. Beware, you might not wanna leave! Located in Venecia de San Carlos, 65km from SJO airport.

Top guest favourite
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
4.99 out of 5 average rating, 122 reviews

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.

Guest favourite
A tranquil swimming pool is framed by palm trees and a rocky outcrop, with clear blue water inviting relaxation. The ocean is visible in the background, where waves gently meet the shore. Lounge chairs are arranged around the pool area, creating a serene atmosphere.
Guest suite in George Town
4.96 out of 5 average rating, 275 reviews

Paradise Escape-Charming Oceanfront Guest Suite

A tranquil oceanfront escape for couples and solo adventurers... Wake-up in bed to a lovely view of a luscious green landscape that melds with the emerald green and blue ocean, sip a hot cup of coffee on the porch, enjoy a sunset cocktail by the ocean front pool, break a sweat in a friendly game of tennis, or take a blanket out to the lawn under the palm trees for breathtaking star gazing. PLEASE NOTE: WE ARE NOT LOCATED ON BATS CAVE BEACH. AIRBNB HAS THIS WRONG!

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
4.99 out of 5 average rating, 179 reviews

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

Top guest favourite
A private heated pool is featured at the edge of the terrace, offering views of the ocean and nearby islands. The clear blue water contrasts with the light-colored stone surrounding the pool, while lush greenery can be seen in the background against a clear sky.
Flat in Little Bay
4.99 out of 5 average rating, 166 reviews

Stunning 2 BD Ocean View - Terraces Lt Bay

Treat yourself to the utmost stylish and modern ocean view apartment located in the exclusive Little Bay Hill . This spacious environment, is designed to be enjoyed as a family, has a terrace with stunning sea views, private pool, one master suites ( Japanese king bed and a walking closet), one bedroom suite with two twin size beds ( could be converted to king size bed ) . Welcome to Terraces Little Bay !

Top guest favourite
Treehouse in Monteverde
4.99 out of 5 average rating, 186 reviews

Magnolia Suite, therapeutic salt Jacuzzi, Monteverde

Bio Habitat Monteverde invites you to live a unique experience surrounded by primary forest. From the balcony, watch animals and enjoy the starry sky in the Net. Relax in our glass jacuzzi with salt water, while watching unforgettable sunsets over the Nicoya peninsula. An exclusive corner where nature, comfort and well-being come together to give you a true paradise in Monteverde.

Top guest favourite
An aerial view of a modern villa is presented, showcasing a private infinity pool surrounded by a spacious deck. Lounge chairs are positioned near the water's edge, with rocky landscaping and lush greenery completing the serene outdoor setting against a clear blue sky.
Villa in Flamenco
5 out of 5 average rating, 112 reviews

Oceanview Glamping at Flamenco w. private pool

Oceanview Villa with private infinity pool Views! Views! Views! Punta Flamenco-Glamping concept is all about breathtaking ocean views, beaches and simple luxuries within nature. Perched on the hillside of Flamenco Beach within the exclusive Punta Flamenco estate, the Glamping is a serene getaway designed for relaxation, privacy, and unforgettable views.

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