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

Guest suite in Port Antonio

Starfish Cottage, Hummingbirds, Mountain, Sea View

IMPORTANT NOTE: We do not accept children under 13. Wake to hummingbirds at your balcony feeder, with views of the Blue Mountain peak, Nonsuch Falls and the Port Antonio coastline. Starfish has a treehouse feel: private bathroom, kitchenette, AC, and a hammock built for doing nothing at all. Swim laps in our 25m pool, train in the open-air Jungle Gym, and reach Frenchman’s Cove in 5 minutes. A quiet retreat for couples and solo travellers who want to disconnect and let the jungle do the rest.

4.97 out of 5 average rating, 246 reviews

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.

4.99 out of 5 average rating, 299 reviews

Guest favourite

Apartment in Montego Bay

Oceanfront 1BR Lux Apt Pool Beach Gym Pickleball

Discover the ultimate tropical retreat at the Soleil Residences, where luxury meets serenity. This elegant oceanfront one-bedroom condominium features a stunning balcony with 180-degree views of the Bay, inviting you to bask in the beauty of Jamaica's coastline. Highlights - Lge Waterfront Pool & Pool Deck * Private Beach Access * Gym * Tennis/Pickleball* Kids Play Area * Gated Community * Fast Fibre WiFi* Chef on request * Spa Services * Concierge Services * Full Time Driver Upon Request

4.94 out of 5 average rating, 158 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.

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

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.

4.97 out of 5 average rating, 115 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

5.0 out of 5 average rating, 202 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 ✌️🇨🇷

5.0 out of 5 average rating, 116 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.

4.97 out of 5 average rating, 224 reviews

Guest favourite

A balcony area features wooden flooring with a table and two chairs positioned to overlook expansive mountain views. A small pool is visible, reflecting the scenery. The sky displays a gradient of clouds during sunset, enhancing the tranquil atmosphere of the natural surroundings.

Treehouse in Monte Verde

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.

4.99 out of 5 average rating, 233 reviews

Top guest favourite

Villa in Christiansted

Mojito Hill - private hilltop pool oasis!

Discover the ultimate St. Croix retreat at Mojito Hill. This 1-bedroom hillside villa offers a front-row seat to the Caribbean, featuring a private navy blue tile pool designed to blend seamlessly with the sparkling turquoise horizon. Located on the serene East End, this is your private sanctuary for spectacular ocean views and tropical relaxation.

4.99 out of 5 average rating, 138 reviews

Top guest favourite

A modern loft structure is framed by lush greenery, featuring large glass windows that allow natural light to fill the interior. The surrounding garden includes tropical plants and a tree, enhancing the natural setting. A pathway of stones leads to the entrance.

Home in Cabarete

Cool new Loft in Las 9 Gotas, Cabarete.

LAS 9 GOTAS is a new eco project in Perla Marina (5 min walk to Perla Marina beach), a loft concept community with 9 lofts surrounded by big trees and nature. OKA loft is Gota 8, a special loft with a private pool and garden, and a private access to the parking lot/street. OKA is Japanese for mountain, green and nature. @estudioguayamuri

4.98 out of 5 average rating, 104 reviews