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, 119 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

A glass-encased jacuzzi is positioned on a wooden deck, offering an unobstructed view of the surrounding hills and valleys. Bright clouds reflect sunlight in the blue sky, enhancing the serene atmosphere of the outdoor space.

Treehouse in Monteverde

4.99 out of 5 average rating, 152 reviews

Suite Magnolia, jacuzzi terapéutico sal,Monteverde

Bio hábitat Monteverde es un lugar con la mejor vistas de Monteverde se encuentra rodeada de la bella naturaleza de nuestro bosque primario. Desde nuestro balcón podrías ver muchos tipos de animales , también disfrutar de las estrellas desde la Net , disfrutaras del bello jacuzzi realizado con cristal, disfruta de la terapia con aguas de sal,mientras aprecias las bellas vistas y atardecer que descansan en la península Nicoya , te encantará nuestro lugar , monteverde un pequeño paraíso del mundo.

Guest favorite

An inviting outdoor space is highlighted by a refreshing pool surrounded by sun loungers and comfortable seating areas. Large glass doors offer a seamless view into the interior, while lush greenery provides a serene backdrop. The patio is ideal for enjoying the fresh air.

Home in San Cayetano de Venecia

4.96 out of 5 average rating, 183 reviews

Quinta La Ceiba Modern Home with Pool in DairyFarm

A contemporary roomy vacation home situated in a dairy farm. Embrace serenity, unwind in a tranquil haven surrounded by cows grazing in lush green fields. It's a birdwatcher's paradise too. This is an ideal escape to disconnect and reconnect with nature. Dine and lounge outdoors make the most of the property's features. Our in-house travel concierge will be glad to arrange tours and activities for you at no additional cost. Consider our private chef service for an even more memorable experience.

Top guest favorite

Cabin in Isabela

4.98 out of 5 average rating, 179 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 favorite

An aerial view captures the geodesic dome surrounded by lush greenery. A wooden deck leads to a private hot tub, while a shaded area features seating under a tent. Soft lighting highlights the surrounding plants, creating an inviting and tranquil outdoor environment.

Dome in Cayey

4.99 out of 5 average rating, 533 reviews

Escape Puerto Rico

¡Vive una experiencia única y mágica de glamping en las hermosas montañas de Puerto Rico! Xcape Dome PR es el lugar perfecto para darte un “xcape” de la rutina y reconectar con la naturaleza. Ubicado en el pueblo de Cayey, PR, a solo 10 minutos de las vías principales. Sumérgete en esta aventura romántica diseñada para parejas, aventureros o viajeros y disfruta de las imponentes montañas, paisajes, flora y fauna, así como, de los detalles únicos que hacen de Xcape Dome PR un lugar especial.

Top guest favorite

An outdoor terrace features a wooden deck with a table and chairs, providing ample seating. A cozy swing chair hangs nearby, surrounded by lush greenery and expansive views of the mountainous landscape. Decorative string lights add warmth to the inviting setting.

Shipping container in Gurabo

4.97 out of 5 average rating, 198 reviews

Vista Linda Haus

At Vista Linda Haus, from the moment you start the journey to the beautiful town of Gurabo, the adventure begins. A unique experience towards the favorite destination. You will find panoramic landscapes, lakes, mountains, farms, cities, and a community with the Puerto Rican warmth of our mountains. Just 35 minutes from the Luis Muñoz Marín International Airport, over 1,000 feet above sea level, you will breathe freedom and peace, in a harmonious environment full of energy and pure nature.

Top guest favorite

Condo in Montego Bay

4.95 out of 5 average rating, 141 reviews

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

Guest favorite

A private glass pool is situated on a cliff with expansive ocean views, reflecting shades of blue and green in the water. The surrounding area is landscaped with greenery, enhancing the sense of seclusion under a clear blue sky.

Place to stay in Quebradillas

4.88 out of 5 average rating, 160 reviews

Shalom on the Cliff (White) Luxury Suite

Enjoy the first private glass pool in all of Puerto Rico. In a unique and exclusive place with one of the best views of the “Isla Del Encanto”. Come and relax on our cliff stage, where you will find the jacuzzi-spa and you can take a nap at the DayBed. Relax with the sound of the sea and connect with the nature of the place. You don't share areas with anyone. Add these services at an additional cost: - Dinner with a chef - Brunch with a chef - Relaxing massage - Decoration in the room

Superhost

An inviting pool area features a curved, tiled pool surrounded by a stone structure. Colorful lounge chairs in red and blue are arranged beside the water. Artistic tile detailing adorns the pool's edge, showcasing a wave design. Lush greenery and vibrant planters add to the ambiance.

Villa in Soufriere

4.87 out of 5 average rating, 190 reviews

Villa Piton Caribbean Castle

Certified to host by St Lucia government. Super private and provides a secure and isolated retreat far from any crowds! We provide cooking service for breakfast lunch or dinner for an extra $20/person/meal. We incorporate heightened cleaning procedures and trained staff. Built by John DiPol, designer of the world-famous Ladera resort, Villa Piton elaborates on the open-aired concept providing breathtaking views everywhere! Extraordinary location and views that need to be seen in person!

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, 133 reviews

Casa de la Tierra y el Mar - 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

An inviting outdoor space features a deep saltwater pool alongside a raised jacuzzi, both surrounded by wooden decking. Lounge chairs are positioned for sunbathing, with a shaded pergola providing shelter. Lush cacti and greenery create a natural backdrop under a soft, sunlit sky.

Home in Paradera

5 out of 5 average rating, 200 reviews

Airstream With Pool, Amazing Ocean & Nature Views

This beautifully appointed Eco friendly 30' Feet Flying Cloud RV is the only luxury Airstream glamping experience in the Caribbean. Located in peaceful nature on the North Coast of Aruba, featuring a private, deep saltwater pool and amazing cacti and ocean views. Exceptional service with attention to detail prioritizing sustainability. Connecting guests to unique local experiences and products, creating a truly one of a kind vacation. Looking for the coolest stay in Aruba? This is it!

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, 174 reviews

les Ramiers

Passez vos vacances à la Villa les Ramiers, là où le soleil vous accompagne dès le lever du soleil et tout au long de la journée. Le logement est indépendant, sans vis à vis , sa petite cuisine et terrasse vue sur la piscine , un top-deck pour profiter du lever de soleil, une grande chambre donnant sur le patio couvert avec coin salon avec la vue sur la mer. Situé sur les hauteurs bien ventilé avec une vue imprenable sur la petite Anse. Parking privé situé à côté de la Villa. Bienvenus