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Vacation rentals with a pool in Caribbean Sea

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Caribbean Sea

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 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, 174 reviews

Private Oceanfront luxurious city villa with pool

Welcome to a beautiful Paradise in Pietermaai District. This 300yr old estate has been restored to perfection after having suffered severe neglect. The unique design style and decoration has been done with love for architecture. The villa can be found in Pietermaai District also known as the ‘Soho of Curacao’’, where monuments meet modern times. With an oceanfront stunning view + private pool, the villa is ideal to get away from it all whilst still be close to great restaurants and live music.

Top guest favorite
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
4.99 out of 5 average rating, 279 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
Home in Playa Zancudo
4.98 out of 5 average rating, 121 reviews

Beachfront Oasis | Private Pool, AC, WiFi

Tucked away in the safe, idyllic tropical rainforest of Costa Rica’s South Pacific Coast, where lush green jungle meets the bright blue Pacific. One of the most biologically diverse regions on Earth, it’s home to Zancudo: a sleepy, off-the-beaten-path fishing village happily untouched by mass tourism. Zancudo delivers all the creature comforts, sodas, grocery shops, bars, local eateries, tours, and plenty to do - making it perfect for adventurers, digital nomads, couples, and families alike.

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, 136 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 favorite
A rooftop terrace features a relaxing hot tub surrounded by lush greenery. Comfortable seating areas include wicker chairs and a wooden table, with stunning views of the city skyline and distant hills under a clear blue sky.
Home in CARTAGENA
4.99 out of 5 average rating, 120 reviews

Casa O Getsemani Luxury Boutique House

Welcome to Casa O Getsemani! Immerse yourself in luxury at this new 4-story haven in in the coolest neighborhoods.Designed by the renowned architect Vladimir Caballero, our house accommodates 6 guests with utmost comfort. Enjoy complimentary one airport transport, delicious breakfast, and attentive housekeepers. Elevate your stay with optional catering, entertainment, and exciting tours. Your unforgettable getaway awaits! Book now and create beautiful memories at Casa O Getsemani.

Top guest favorite
Apartment in Tamarindo
4.99 out of 5 average rating, 363 reviews

Lower Casita Catalina in Tamarindo w Private Pool

From this hilltop location above Tamarindo Bay, you will enjoy a panoramic view that is unbelievable. You’ll see what we mean when you get here! The Casita offers a king bed and a pull-down Queen bed, fully equipped with a private bathroom, kitchen, and a small balcony with ocean views and perfect for watching monkeys in the surrounding trees! You will also have access to the property's social space including a breezy covered terrace by the ocean-view pool and rooftop lounge!

Top guest favorite
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 Monteverde
4.97 out of 5 average rating, 103 reviews

Luxury villa & Infinity Pool

Sumérgete en la tranquilidad y belleza natural con esta espectacular casa en medio del bosque, diseñada para ofrecerte una experiencia única de lujo y relajación. Esta propiedad combina elegancia moderna con el encanto de la naturaleza. Despierta con los sonidos del bosque y disfruta de la paz que solo este entorno natural puede brindar. La casa ofrece privacidad total, pero se ubica en el corazón de Monteverde a corta distancia en auto de restaurantes locales y tiendas.

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, 607 reviews

Escape Puerto Rico | Luxury Dome + Pool + Views

Escape to a romantic and luxurious glamping dome surrounded by the lush mountains of Cayey, Puerto Rico🌿. Enjoy total privacy with a private heated pool, panoramic views, and elegant design — the perfect retreat for couples or solo travelers seeking peace, comfort, and connection with nature. Wake up to mountain sunrises, relax under the stars, and experience a serene escape just an hour from San Juan — were nature and luxury meet in perfect harmony.

Top guest favorite
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
4.99 out of 5 average rating, 194 reviews

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

Guest favorite
An aerial view captures a serene pool surrounded by lush greenery and palm trees. The area features lounge chairs for relaxation, and the surrounding landscape showcases a variety of trees and plants, creating a peaceful atmosphere.
Cabin in San Sebastián
4.97 out of 5 average rating, 122 reviews

Deer Cabin | Heated Pool & Total Privacy

🌿 Private Romantic Escape in Nature Deer Cabin is the perfect getaway for couples looking to relax, reconnect, and enjoy complete privacy surrounded by nature. Enjoy a private heated pool, cozy outdoor bed, fire pit area, air conditioning, and a fully equipped kitchen for a comfortable and unforgettable stay. Every corner is designed for peace, romance, and relaxation under the stars. At Deer Cabin, you don’t just stay… you experience.

Top guest favorite
Villa in La Fortuna
4.98 out of 5 average rating, 334 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 Jacuzzi Campfire area High-speed fiber optic Wi-Fi Located 1.5 kilometers from the main road on top of a private hill where you will be surrounded by flora and fauna. 1 day pass included to the nearby resort's hot springs Base rate for 2 people + $50 Additional person. A vehicle is recommended.

Top guest favorite
A tranquil outdoor pool is surrounded by lush tropical foliage, providing a serene atmosphere. The clear water reflects the vibrant greenery nearby. A glimpse of a rustic yellow house can be seen in the background through the plants.
Tiny home in Añasco
4.93 out of 5 average rating, 420 reviews

Disconnect in a tiny house in rural Puerto Rico

Experience the perfect harmony of rustic charm and modern comfort at Tiny House @ Finca Figueroa. Escape the city to reconnect with nature, waking up to bird melodies and breathtaking views of lush, rolling fields. This intimate sanctuary is designed for two guests (included in the rate), with the option to add guests for a small additional fee. Breathe in the fresh air and rediscover tranquility in your own private, green paradise.

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