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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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An aerial view showcases the modern villa nestled among sandy surroundings and greenery. A wooden deck frames the plunge pool, with lounge chairs arranged conveniently nearby. The villa's exterior features a light blue color, and steps lead up to the welcoming porch.

Cottage in Rainbow Bay

4.93 out of 5 average rating, 166 reviews

Villa Soreli - 1 B/R Oceanfront w/Pool

Villa Soreli, a brand new bespoke Ocean Front Luxury Villa rental in Rainbow Bay, Eleuthera Bahamas (NOT NASSAU). This 1 B/R private villa includes a Queen-sized Master bedroom with an additional King-size Sleeper Sofa to accommodate a family of 4. Our villa is fully equipped with a full kitchen, indoor & outdoor shower, high end finishes & a plunge pool overlooking the Caribbean Sea. It is walking distance to Rainbow Bay Beach. Nestled in between the Caribbean Sea and the Atlantic Ocean.

Top guest favorite

An aerial view showcases a private pool surrounded by a stone deck. Lounge chairs, a shaded area with a sail canopy, and colorful pool floats enhance the space. A pool table and landscaped pathways are visible, providing a serene outdoor atmosphere.

Apartment in Guerrero

4.97 out of 5 average rating, 370 reviews

Private Pool and Entertainment Area at Lunabelapr

Plan a relaxing getaway while enjoying a private pool with sundeck, fire pit, 100-inch screen projector, gazebo, and pool table that are exclusive for the guests of Lunabela. This special place is just a 10-minute drive from both the beach and Guajataca River, and within walking distance to the mall, restaurants, and bakeries, making it easy to plan your visit and explore Isabela. The unit has a fully stocked kitchen, AC, king-size bed, Wi-Fi, TV, free parking space, BBQ grill, and board games.

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, 197 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

A tranquil outdoor pool is seen, featuring a sunbathing area with two sleek lounge chairs. The pool's clear water reflects the bright blue sky with fluffy clouds, while tropical plants enhance the scenic mountainous backdrop.

Tiny home in Naguabo

4.99 out of 5 average rating, 142 reviews

Casa Suiza (Mountainous Area)

Casa Suiza es un lugar para escapadas románticas, sólo para parejas. Estamos ubicados en lo alto de la montaña, es muy privado y alejado de la ciudad, a una hora de distancia de San Juan y el Aeropuerto Internacional de Puerto Rico. Tenga en cuenta que dirigirse a nuestra propiedad es por calles con curvas y algunas pendientes empinadas, pero completamente transitables. Recomendamos rentar un vehículo SUV o un 4x4 para su tranquilidad, si no está acostumbrado a transitar en la Montaña.

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

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, 131 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.

A cozy chalet is nestled in a lush green landscape, featuring a red roof and warm yellow exterior. A private heated pool is visible, surrounded by a wooden deck, and scenic hills are seen in the background under a colorful sunset.

Chalet in Caguas

4.99 out of 5 average rating, 164 reviews

Chalet De Los Vientos (Chalet of the Winds)

Chalet de Los Vientos is a beautiful and cozy tiny house located in 25 acres , in the mountains of Caguas , PR at 2000ft above sea level with a spectacular view, heated pool and the privacy you deserve! This Chalet is a couples retreat and the perfect getaway for you and your loved one to disconnect from the daily routine. If you love coffee as much as we do, there is a dedicated coffee bar for you to make your espresso drink. We also have a 19Kw Caterpillar backup generator 💡

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, 150 reviews

Magnolia Suite, therapeutic salt Jacuzzi, Monteverde

Bio Habitat Monteverde is a place with the best views of Monteverde. It is surrounded by the beautiful nature of our primary forest. From our balcony you can see many types of animals, also enjoy the stars from the Net, enjoy the beautiful jacuzzi made with glass, enjoy the therapy with salt water, while you appreciate the beautiful views and sunset that rest on the Nicoya peninsula, you will love our place, Monteverde a small paradise of the world.

A private pool is surrounded by a wooden deck, showcasing a serene view of lush greenery and distant hills. A small table and two chairs are positioned on the deck, inviting relaxation as the sun sets behind the mountains.

Villa in Pedro García

4.95 out of 5 average rating, 149 reviews

Villa Bambú Sunset, 360 view, heated pool

Bambu Sunset, your unique villa for two, is a private and romantic retreat where the beauty of the mountains blends with breathtaking sunsets. This smart home offers exceptional amenities: a heated pool, allowing you to immerse yourself in luxury and comfort while enjoying the surrounding nature. Experience serenity and sophistication in this exclusive getaway spot.

The image presents a modern cabin overlooking rolling hills, with a spacious outdoor deck and lounge chairs. A sleek swimming pool occupies one side, reflecting the clear blue sky. Mountains can be seen in the background, emphasizing the tranquil outdoor setting.

Cabin in Pedro García

4.96 out of 5 average rating, 153 reviews

Dreamy Alpine: Pool with Unparalleled Views

A noir cabin- Aframe at the mountains of Pedro Garcia is an architecturally designed one bedroom cabin located less than 55 minutes drive from santiago de los caballeros . Designed with a slow pace in mind, with epic escarpment and mountains views , the AFrame is a place to reset, reflect and connect with nature.

A sunlit deck features comfortable loungers with a straw hat resting on one. Lush greenery surrounds the space, while the iconic Pitons rise majestically in the background against a vibrant blue sky and tranquil sea.

Villa in Soufriere

4.99 out of 5 average rating, 132 reviews

La Batterie Villa • Boutique Villa • Amazing Views

Tucked away in the exclusive Anse Chastanet / Jade Mountain area of Soufriere, La Batterie villa offers complete privacy. The villa is fully staffed to enhance your vacation experience. You will find your escape at this luxury villa surrounded by lush tropical gardens with views of the Pitons and Caribbean Sea.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Popular amenities for Caribbean rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A sunny outdoor space features a large heated saltwater pool surrounded by lush palm trees and vibrant tropical plants. Comfortable lounge chairs are positioned poolside, accompanied by a small table. The tranquil setting offers an ideal space for relaxation and enjoyment.

4.92 out of 5 average rating, 196 reviews

Private Pool and Tropical Garden Oasis

A charming guest house is surrounded by lush greenery and vibrant flowers. The open terrace features a spacious sleeping area with a cozy bed and seating arrangements, integrating nature with comfort. Soft lighting enhances the inviting atmosphere for relaxation and enjoyment.

4.93 out of 5 average rating, 382 reviews

Beautifull Guest House with panoramic views

Top guest favorite

Home in San Nicolas

5 out of 5 average rating, 155 reviews

Ocean Front Family Vacation Home, at Baby Beach

The exterior of the house features a private pool surrounded by a spacious grassy area. A wooden deck with seating is situated at the back, providing a relaxing spot to enjoy the outdoors. Lush palm trees frame the setting, creating a serene atmosphere.

Home in Pompano Beach

4.97 out of 5 average rating, 127 reviews

•Floasis• Your private FL oasis 5 min to beach!

Top guest favorite

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, 226 reviews

Aruba Private Resort. Its All Yours and Only Yours

Top guest favorite

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, 160 reviews

Private Oceanfront luxurious city villa with pool

Top guest favorite

A private heated swimming pool is visible in the foreground, surrounded by tiled borders. Steps lead up from the pool to a two-story white house with multiple windows and balconies. Lush greenery and a white chair complement the outdoor space.

4.97 out of 5 average rating, 379 reviews

Monte Niebla, a piece of heaven in the mountains

An infinity pool extends beside a covered outdoor seating area featuring bright orange chairs. Lush green hills and the ocean are visible in the background, while a ceiling fan offers comfort in the shaded space under a modern roof.

Home in Río San Juan

4.94 out of 5 average rating, 125 reviews

VeoMar - Casita Axel 4 bdr villa w/ endless views

Condo rentals with a pool

Top guest favorite

A serene courtyard is framed by two-story residential buildings, featuring a sparkling pool at the center. The pool is surrounded by sun loungers, with palm trees dotting the landscape, creating a calm and inviting space for relaxation.

Condo in Punta Cana

4.94 out of 5 average rating, 119 reviews

A beautiful apartment 600 meters from the beach

A serene outdoor space is showcased, featuring a shaded gazebo surrounded by palm trees and manicured greenery. In the background, a swimming pool is visible, with residential buildings partially framed by the lush hillside.

Condo in Ocho Rios

4.92 out of 5 average rating, 108 reviews

The Ocean Ridge - Ocho Rios, Stunning Sea Views

Top guest favorite

A bright living area showcases expansive glass doors that open to a private balcony with views of the ocean. Comfortable seating arrangements include a sectional sofa and two outdoor chairs. A modern coffee table sits centrally on a textured rug, enhancing the open and inviting atmosphere.

Condo in Carolina

4.95 out of 5 average rating, 102 reviews

Deja Blue BeachFront Apartment @ Isla Verde (Green Island)

The living area features a spacious blue tufted sofa complemented by a sleek glass coffee table. A modern accent chair adds contrast, while large sliding glass doors provide ample natural light and stunning views of the surrounding skyline.

4.92 out of 5 average rating, 111 reviews

Make It Happen! Brand New with Amazing Water Views

A private swimming pool is illuminated by soft lighting, surrounded by lush greenery. The pool features shallow steps for easy access and showcases a clean, inviting water surface. The area is designed to blend relaxation with natural beauty.

Condo in Punta Cana

4.9 out of 5 average rating, 184 reviews

Charming beach apartment with private Pool

Top guest favorite

Condo in Montego Bay

4.95 out of 5 average rating, 140 reviews

1br Lux Oceanfront Apt Pool Beach Gym Pickleball

A neutral-toned master bedroom presents a queen bed layered with plush pillows and a soft throw. Flanking the bed are two bedside lamps, providing a gentle glow. A decorative piece featuring fish artwork adorns the wall, complemented by a window with horizontal blinds.

Condo in Pompano Beach

4.85 out of 5 average rating, 242 reviews

ON CANAL! Pool+Walk to BEACH! Boat Watch! 1b/1b

Top guest favorite

An expansive balcony offers a breathtaking view of the coastline and a serene pool area surrounded by palm trees. Clear blue skies and ocean waves create a tranquil setting, inviting moments of relaxation and enjoyment.

Condo in Juan Dolio

4.94 out of 5 average rating, 166 reviews

Caribbean Comfort I

Home rentals with a private pool

An inviting rooftop terrace features a hanging chair and comfortable cushioned seating. A wooden coffee table stands at the center. Lush greenery provides a natural backdrop with trees visible, and the sky showcases soft clouds, creating a serene outdoor atmosphere.

Home in Santo Domingo

4.94 out of 5 average rating, 418 reviews

Gorgeous Colonial House near Cafes and Bars

Top guest favorite

A heated saltwater pool is framed by lush greenery, providing a sense of privacy. The pool features a decorative wall at one end, adding an elegant touch. The surrounding patio offers a clean, open space for relaxation.

Home in West Palm Beach

4.95 out of 5 average rating, 177 reviews

Soak up the Beachy Vibe at a Vibrant Poolside Paradise

An inviting outdoor area features a clear blue pool with a built-in seating area. The covered patio provides shaded seating options. Expansive ocean views are visible in the background, framed by a bright blue sky and a few scattered clouds.

Villa in Christ Church

4.95 out of 5 average rating, 39 reviews

Retreat Style, Sea Views W/ Private Pool & Hot Tub

An outdoor patio area is featured with a wooden dining table set for six, accompanied by lounge chairs. A sparkling pool is visible in the background, surrounded by lush greenery and the striking architectural elements of the home, including an aged stone wall.

Villa in Santo Domingo

4.93 out of 5 average rating, 348 reviews

Casa Pantheon Luxury Colonial House

Bright art-filled space features high ceilings with wooden beams. Colorful paintings adorn the walls, drawing attention to the gallery-like atmosphere. A mix of wicker seating and wooden chairs is arranged around a central table, complemented by a vibrant vase and fresh flowers.

Villa in CARTAGENA

4.87 out of 5 average rating, 157 reviews

Old City Villa - Breakfast & Housekeeping Included

A private pool sits surrounded by lush ferns and a stone wall, providing a tranquil setting. A patio area features a dining table under an umbrella, creating a space for outdoor relaxation. The pool's blue tiles reflect sunlight, enhancing the serene environment.

Townhouse in CARTAGENA

4.87 out of 5 average rating, 219 reviews

Walled City Luxurious Townhouse With Private Pool

A panoramic view from a high-rise balcony captures the expansive coastline meeting the city's skyline. Various buildings, including modern high-rises and low-rise structures, line the streets, with the ocean stretching towards the horizon under a cloudy sky.

Condo in San Juan

4.9 out of 5 average rating, 268 reviews

Condado Beach Views by Cesar 2501

A serene pathway lined with tropical plants leads to a stone table, surrounded by lush greenery and vibrant palms. The path is paved with bricks, creating a welcoming entrance to a private garden area.

Guesthouse in West Palm Beach

4.97 out of 5 average rating, 178 reviews

Tropical Cabana with Pool and Bedroom

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