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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
An aerial view of the villa highlights its modern architectural design, featuring an infinity pool that extends toward the Caribbean sea. Lush greenery surrounds the property, and spacious outdoor areas are seen next to the pool, providing ample space for relaxation and enjoyment.
Home in Playa Jeremi
5 out of 5 average rating, 29 reviews

Overseas

Overseas sits on a clip overlooking the turquoise Caribbean sea. The villa is designed to take in its beauty from every room in the house. Enjoy the scenery while sipping a drink in the infinity pool or venture down the private stairs to snorkel in the ocean where you can enjoy the company of sea turtles and dolphins on a lucky day. Adventure lovers are spoiled with world class diving spots and lush nature reserves in the vicinity. Just be back in time to admire the sunset from the pool deck.

Top Guest favourite
Loft in La Fortuna
4.97 out of 5 average rating, 190 reviews

Natural & Cozy Arenal Getaway

Un hospedaje para escapar de la rutina y conectar con la naturaleza, tiene un diseño moderno con una cálida decoración, rodeado de naturaleza donde podrás observar muchas aves, una linda vista al volcán, balcón, terraza, una refrescante piscina y jacuzzi privado. Un lugar ideal para parejas, amigos o para que puedas teletrabajar tranquilamente. Ubicados estratégicamente cerca de todas las actividades principales y a tan solo 2.5 km del centro de La Fortuna y a 1 km de La catarata La Fortuna.

Top Guest favourite
An entrance is framed by open louvered doors, leading to a stylish living space bathed in evening light. A cozy seating area faces large windows that showcase a scenic view of the sunset over the sea, with greenery and decorative elements enhancing the ambiance.
Villa in Treasure Beach
5 out of 5 average rating, 88 reviews

Treasure Beach Oceanfront Sanguine Villa

Sanguine's spacious fully staffed beachfront Villa with an infinity pool is located in Treasure Beach on Jamaica's South Coast. Home to the renowned Calabash Literary festival. 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 to go home with, you sit back and relax while we do the grocery shopping and look after you.

Top Guest favourite
Guesthouse in Venecia
5 out of 5 average rating, 39 reviews

Treetop cabin with hot tub, pool & trails

Brand new cabin from experienced local host 🙌🏼 Nestled in a private primary rainforest, Ananda offers an unique retreat where nature & comfort meet. Unwind in your private balcony hot tub, listen to the soothing sounds of nature, and embrace the peace of the rainforest. This modern boutique cabin features a fully equipped kitchen, an unique bedroom with nature views, and a modern bathroom designed for relaxation. Located in Venecia, San Carlos, 65 km from SJO Airport. Local owned ✌️🇨🇷

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, 102 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 serene outdoor area is illuminated at night with colorful lights reflecting in a resort-sized pool. Chic palapas are situated nearby, surrounded by palm trees. The vibrant atmosphere is enhanced by strategically placed plants and flowers along the edges.
Home in Palm Beach
5 out of 5 average rating, 239 reviews

Aruba Private Resort. Its All Yours and Only Yours

Welcome to Casa Carmela. Relax in the resort sized pool and outdoor oasis. Melt the day away under the exotic palapas or toast your buns in the sun. Whatever your pleasure, Casa Carmella aims to please. She’s a short walk to Palm Beach one of the top rated beaches in the world. Restaurants, casinos and nightlife are walkable as well. She comes with a comfy king size bed, gas grill, fully equipped kitchen, beach chairs & beach towels and cooler. This is all yours and only yours.

Guest favourite
An open-air living space features comfortable seating arranged around a wooden table. Large sliding doors frame stunning views of the turquoise waters and distant hills, with sunlight illuminating the area. Coastal decor complements the relaxation zone, inviting guests to enjoy the scenery.
Villa in Cul-de-Sac
5 out of 5 average rating, 50 reviews

Only Villa with private beach Beach Villa Cala Mar

Optic-fiber wifi, heated swimming pool and private white sand beach! Snorkeling gear and kayaks included. Private Chef, Masseuse & Concierge on demand. Move into this paradise, exclusively designed for your stay to be absolutely perfect. Enjoy every part of it, from the exquisite decoration, the quality of every single component of the Villa, its relaxing white sand beach and all the features included (kayaks, snorkeling gear, beach towels, complimentary drinks & snacks.

Top Guest favourite
Villa in La Fortuna
4.98 out of 5 average rating, 294 reviews

Villa Bromelia, A Volcano in your Garden!

La Villa vacacional con la más cercana y ESPECTACULAR vista al Volcán Arenal. A 10 minutos del centro de La Fortuna Totalmente equipada Jacuzzi privado Zona de fogata Wi-fi de fibra óptica de alta velocidad Ubicado a 1.5 kilómetros de la carretera principal en lo alto de una colina privada en la que estarás rodeado de flora y fauna. 1 day pass incluido a las aguas termales del resort cercano Tarifa base para 2 personas +50$ Persona adicional. Se recomienda vehículo.

Top Guest favourite
A vibrant coastal view is framed by lush green foliage, showcasing calm turquoise waters under a clear blue sky. Gentle waves are seen lapping at the shore, with distant hills creating a serene backdrop against the horizon.
Apartment in East End
4.96 out of 5 average rating, 204 reviews

Waterfront Cottage, St. Croix US VI

"30 Steps to Paradise" Sweet and cool 1-bedroom cottage with large porch attached to a family home, with complete privacy. Hear the sound of the waves and walk to several beaches. Located near Jack's Bay on the south east tip of the island. The cottage has ceiling fans, no air-conditioning. The pool is available for guests. The other name for the cottage is "30 steps to Paradise" because it has 30 steps from the road to the entrance of the cottage.

Top Guest favourite
A sweeping view captures the vibrant turquoise waters of the coastline, framed by lush green hills. Islands dot the horizon under a clear blue sky, while the wooden railing in the foreground provides a picturesque viewing point of the landscape.
Guesthouse in BL
4.98 out of 5 average rating, 180 reviews

les Ramiers

Spend your holidays at Villa les Ramiers, where the sun is with you from sunrise and throughout the day. The accommodation is independent, not overlooked, with its small kitchen and terrace overlooking the pool, a top-deck to enjoy the sunrise, a large bedroom overlooking the covered patio with lounge area with sea view. Located on the well-ventilated heights with stunning views of Petite Anse. Private parking is located next to the Villa. Welcome!

Top Guest favourite
A colorful hammock is suspended between two palm trees, inviting relaxation beside a sparkling pool. Lush tropical plants surround the outdoor area, creating a peaceful ambience. The inviting pool area is visible in the background, enhancing the serene outdoor setting.
Guest suite in Homestead
5 out of 5 average rating, 164 reviews

“Have Fun at Hacienda Paraíso” Suite 1 | pool |

Welcome to Room 1, the first addition at Hacienda Paraíso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.

Top Guest favourite
Home in Saint Martin
5 out of 5 average rating, 9 reviews

Villa Josefa SXM · Ocean View Above Friar’s Bay

✨ Perched above Friar’s Bay, this villa offers a breathtaking view from Maho to Anguilla. 🏡 3 ocean-view master suites, kitchen ready for a private chef. Upstairs, a covered terrace becomes a peaceful refuge facing the sea for up to 10 guests. 🌊 Pool surrounded by a suspended deck, pergola & evening serenity. 🌴 Gated residence, beaches within walking distance. Here, luxury, nature and sunsets are lived more than described.

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