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Holiday 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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Luxe
Apartment in Tulum
4.97 out of 5 average rating, 148 reviews

Airbnb Luxe | Mayan-Inspired Villa | Top Rated

Experience the epitome of Tulum-style elegance at our Bohemian Chic Residence with style, comfort, and convenience. TEMPLIA is a unique, luxurious 2BR/2BA home with a private pool, outdoor hot tub, and award-winning Mayan-inspired design with fully equipped kitchen, concierge service, fast WiFi, and any additional service needed. Discover a harmonious blend of luxury and comfort perfect for travelers who value design, privacy, and quality.. Unforgettable moments await in refined Tulum living!

Top Guest favourite
A modern villa is showcased alongside a serene waterfront. An inviting pool reflects the colors of the sunset, while lounge chairs are positioned nearby. The spacious outdoor area is bordered by lush greenery, and large windows provide views into the interior living spaces.
Home in Punta Rucia
4.99 out of 5 average rating, 109 reviews

Villa Mare - Ocean Front

Villa Mare is a luxurious beachfront villa offering the perfect blend of comfort and privacy. With a large climatized pool, direct access to the beach, and stunning ocean views, it’s ideal for families and groups looking to unwind. Enjoy the convenience of daily housekeeping, chef services, and a range of exciting excursions like Cayo Arena, ATV rides, and catamaran trips. Make lasting memories and relax in paradise at Villa Mare, where every detail is designed for your comfort and enjoyment.

Top Guest favourite
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, 197 reviews

Casa Suiza-Private Couple Escape with Heated Pool

Casa Suiza es un retiro de escapadas románticas, sólo para parejas con Piscina Climatizada. Estamos ubicados en la montaña, es muy privado, alejado de la ciudad, a una hora de distancia de San Juan y el Aeropuerto Internacional de Puerto Rico. Recomendamos rentar un vehículo SUV o 4x4 para su tranquilidad, si no está acostumbrado a transitar en la Montaña. Una vez comienzas a subir a la montaña, es por calles con curvas y algunas pendientes empinadas, pero completamente transitables.

Top Guest favourite
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, 124 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.

Luxe
Villa in Santa Teresa
4.94 out of 5 average rating, 127 reviews

Villa Lasai - Brand New Luxury Villa

Villa Lasai is a 280m² luxury 3 Bedroom vacation home, built on 2 levels and sleeps up to 6 people. Elegantly constructed with a great mix of tropical architecture, styled with materials such as exposed polished concrete and natural stone as the indoor and outdoor areas blend together. Facing the ocean and jungle, enjoy the view from the 25m² saltwater pool. Villa Lasai is conveniently located less than a 3 minute drive to the world-class surfing beaches and downtown Santa Teresa.

Top Guest favourite
An outdoor area features a rectangular swimming pool with clear water, surrounded by a deck area with lounge chairs. A striped umbrella provides shade, while views of the ocean and sandy beach create a serene backdrop. Lush greenery frames the space, enhancing the coastal ambiance.
Villa in Providenciales
4.99 out of 5 average rating, 140 reviews

Villa DelEvan 4A / 1-bedrm Beach front villa

Centrally located on the Grace Bay Beach, a perfect place for luxury, rest & tasting the best island cuisine. Close to everything you need for a great vacation: Walking dist. from 4 restaurants - Mango Reef, Shark Bite, Baci & Simone’s. 10 min drive to the famous island Fish Fry, 15 min drive to the Airport, 5 min drive to the supermarket. Gated property, private parking, 24hr security. Boating/fishing/sightseeing/wind surfing & more. Water sports pick-up on property.

Top Guest favourite
An infinity pool cascades gently into a lower plunge pool, surrounded by lush greenery. The sparkling water reflects the sunlight, while the shimmering sea is visible in the background, enhancing the serene outdoor setting.
Villa in Treasure Beach
5 out of 5 average rating, 103 reviews

Summer Special Treasure Beach Sanguine Villa

Sanguine's spacious fully staffed beachfront Villa with an infinity pool is located in Treasure Beach on Jamaica's South Coast. 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, you sit back and relax while we do the grocery shopping and look after you. Message me re airport and transport options

Luxe
Loft in Tulum
4.99 out of 5 average rating, 137 reviews

Casa Copal Luxury Design Penthouse with Pool

Luxury Design Penthouse located in Tulum what comes with unique features as double hight ceiling living, large Rooftop Pool, a luxury high end speaker system from Bang & Olufsen, beautiful bed textiles and large spaces with unique decoration located in the most trendy Area of Tulum. Beside concierge services the property offers 2 high speed fiber optic internet networks for the best service in Tulum. This serene, elegant and quiet place is a Design Heaven!

Guest favourite
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, 613 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 favourite
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, 197 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

Top Guest favourite
An outdoor dining area features a wooden table surrounded by four chairs. Large windows provide a view of lush greenery and the pool area. Soft sunlight filters through trees, creating a warm atmosphere. Decorative items are arranged on the table.
Condo in Playa Santa Teresa
4.99 out of 5 average rating, 299 reviews

Purapura _Jungle House w/ pool, walk to beach

Apartamento JUNGLE HOUSE Precioso alojamiento a nivel de jardín y piscina, con una amplia terraza, en una ubicación inmejorable en Santa Teresa. A distancia a pie de la playa, los mejores restaurantes y tiendas. Nuestro Jungle House dispone de piscina que comparte con otros huéspedes, con vistas al atardecer. Un alojamiento cómodo y céntrico, que te brinda todo lo que necesitas. Solo 300m de la playa Santa Teresa (4 minutos caminando)

Guest favourite
Treehouse in Monteverde
4.99 out of 5 average rating, 226 reviews

Magnolia Suite, therapeutic salt Jacuzzi, Monteverde

Bio Habitat Monteverde invites you to live a unique experience surrounded by primary forest. From the balcony, watch animals and enjoy the starry sky in the Net. Relax in our glass jacuzzi with salt water, while watching unforgettable sunsets over the Nicoya peninsula. An exclusive corner where nature, comfort and well-being come together to give you a true paradise in Monteverde.

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