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Vacation 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 favorite
A private pool deck features a refreshing blue pool surrounded by lush greenery. New patio furniture includes two chaise lounges and a table for four, complemented by a gas grill. Views of the ocean create a peaceful outdoor atmosphere under a clear blue sky.
Villa in Christiansted
5 out of 5 average rating, 121 reviews

Mojito Hill - private hilltop pool oasis!

Beautiful 1-bedroom ocean view villa with private pool. Relax on the private pool deck with brand new patio furniture featuring chaise lounges, table seating for 4, and a gas grill. Sweet dreams await you in the four-poster king sized master suite, complete with french doors that open to the pool deck and allow for the ocean breezes to keep you cool. The shower is a fully stocked oversized marble shower with room for two. A fully equipped kitchen with granite countertops and modern appliances, including a Keurig latte machine, will make you feel right at home. Mojito Hill includes many conveniences such as a smart TV, wifi, air conditioning, washer/dryer, and much more. Extra guests are no problem, as the couch features a pull-out bed. Villa Madeleine is a gated community on St. Croix’s relaxing East End, where you will enjoy the privacy, amazing views, tennis court, and close proximity to the Reef Golf Course, Duggan’s Reef restaurant, Divi Casino and Resort, Grapetree beach to the south and Reef Beach to the north. All these amenities are within walking distance, but do require traversing a steep hill, so driving is typically preferred. We have an on-island manager, and Tom & Hillery are available at any time via email/text/phone if needed. If you don't see the dates you are looking for, please message us, we also have a Splash of Lime in the same complex that has a spectacular northern facing view.

Top guest favorite
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, 26 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 favorite
The exterior view of Casa Victoria showcases a modern structure adjacent to a vibrant pool. The pool features a rich blue hue and a unique design that includes seating at the water's edge. Lush greenery surrounds the property, enhancing its natural appeal.
Cottage in La Fortuna
4.99 out of 5 average rating, 159 reviews

Casa Victoria, at the foot of the mountain

Casa Victoria is located in the town of Chachagua, less than 11 kilometers (6 miles) from La Fortuna and surrounded by an impressive rainforest. Located in a safe and family-friendly neighborhood, full of plantations and picturesque views. A beautiful and comfortable farmhouse for 10 people where you can enjoy the tranquility and peace of this area, and at the same time very close to tourist and natural attractions, national parks, restaurants and entertainment offered by the San Carlos area.

Top guest favorite
A modern boutique cabin is positioned amidst lush trees, with gentle fog enveloping the landscape. A wooden walkway leads to the cabin entrance, which is illuminated quietly. Surrounding greenery enhances the natural atmosphere, offering a sense of seclusion and tranquility.
Guesthouse in Venecia
5 out of 5 average rating, 14 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 favorite
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, 94 reviews

Sun and Moon Mountain Retreat

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 favorite
A beachfront view is presented from a spacious patio, featuring white railing and tropical palm trees swaying in the gentle breeze. The vibrant blue ocean waters are visible beyond the sandy beach, under a bright sky dotted with clouds.
Condo in Manatí
4.98 out of 5 average rating, 117 reviews

Beachfront Luxury @ Mar Chiquita

Welcome to the secluded peaceful & modern Seaside Escape at Playa Mar Chiquita. Remodeled & furnished to give you a clean luxurious 5 star experience. Our top floor unit gives unmatched views of the Atlantic & legendary sunsets of Puerto Rico. Its beachfront patio is complete w/ gas grill sink & furniture. The sundeck leads you to an almost private beach while the soft patio lights adorning the tree will keep you under the stars all night. A quiet paradise with Mar Chiquita only steps away.

Top guest favorite
A serene outdoor area features a sparkling pool surrounded by lush greenery and tropical plants. A shaded seating area is provided by a large umbrella, along with a cozy hanging chair in the background. The peaceful ambiance is enhanced by bright blue skies.
Guest suite in Luquillo
5 out of 5 average rating, 190 reviews

Casa Encanto - Experience El Yunque Rainforest.

This Guest Suite, on the lower level of our exclusive luxury villa, Casa Encanto, is the perfect tropical getaway. Nestled in the peaceful and lush foothills of the El Yunque Rain Forest, Located in Luquillo with many nearby attractions. You’ll have easy access to downtown Luquillo, El Yunque National Rainforest, Luquillo Beach, Caribali Adventure Park, Las Paylas, charter boat trips, snorkeling, zip lines and much more. The Guest Suite is fully solar with Tesla Batteries and backup water

Top guest favorite
A modern sanctuary is showcased amidst lush tropical foliage, featuring an inviting plunge pool. The structure's open design highlights floor-to-ceiling glass walls, allowing natural light to fill the interior. A vibrant sunset sky adds warmth to the scene, enhancing the tranquil surroundings.
Villa in Mal Pais
4.97 out of 5 average rating, 138 reviews

House of the Earth and the Sea - stunning luxury

Escape to La Casa Tierra y el Mar: A romantic luxurious mountain top sanctuary where architecture meets wilderness in Costa Rica's Nicoya Peninsula. Breathtaking ocean views, plunge pool, and wildlife at your doorstep. Gourmet kitchen, indoor outdoor living. Moments from pristine beaches, this architectural marvel offers the perfect blend of privacy, comfort, and adventure. Your secure and completely private tropical dream retreat awaits—where extraordinary design meets untamed nature.

Top guest favorite
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, 176 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 favorite
A private jacuzzi is highlighted in the foreground, showcasing clear water reflecting the scenery. In the background, Arenal Volcano rises, partially shrouded in clouds, with a lush green landscape surrounding it. Comfortable lounge chairs are positioned nearby for relaxation.
Villa in La Fortuna
4.98 out of 5 average rating, 280 reviews

Villa Bromelia, a volcano in your garden!

The vacation villa with the closest and most SPECTACULAR view of Arenal Volcano. 10 minutes to downtown La Fortuna Fully equipped Private hot tub Grill and fire pit area Optic fiber high speed Wi-Fi Located 1.5 kilometers from the main road at the top of a private hill where you will be surrounded by flora and fauna. All guests can enjoy the 1-day pass to the nearby resort's hot springs Base rate for 2 people A vehicle is recommended.

Top guest favorite
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, 149 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 favorite
A striking A-frame house is illuminated at night, showcasing its wooden exterior and large glass front doors. Lush greenery and neatly arranged stones adorn the pathway leading up to the entrance, while subtle lighting enhances the surrounding landscape.
Cabin in Aguadilla
5 out of 5 average rating, 132 reviews

Blackandwoodcabin Cabin/chalet in Aguadilla

****Actividades privadas tienen un costo adicional y deberá ser coordinada y aprobada por la Gerencia. Tenemos piscina de agua salada, jacuzzi todo calentador. Un cuarto con tina 🛀. Un cuarto con sofá cama y televisor. Cocina completa, microondas, una lavadora y secadora. Además tenemos una vinera. Planta eléctrica de 20k y cisterna con bomba de agua. Sistema de riegos para los jardines de ensueño. Iluminación nocturna en armonía.

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