
Holiday rentals with a pool in West Indies
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in West Indies
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Casa Anya @ Hilltop (private infinity plunge pool)
Imbuing Culebra’s magic with passionate India, Kavita’s native land, Casa Anya wraps you in contemporary airy spaces caressed by Indian linen. Savor bay and lush mountain vistas from a soothing rainfall grotto shower leading to a private plunge pool, and a full kitchen for romantic dining. Sliding doors to the deck invite in sunsets, stars, and enchanting breezes with chirping coquís. Fall into a king bed, and wake to pink dawns. Anya means grace in Hindi; let it grace your Caribbean dreams.

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.

Hacienda Sol y Luna 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.

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.

Sea Loft Vue imprenable - piscine privée
* Loft de 200m² * Vue mer exceptionnelle * Piscine privée * A 250 mètres de la petite plage de Galisbay * Terrasse avec chaises longues, salon de jardin, table d'extérieur et BBQ * Espace bureau * Wifi 100 Mbps * TV avec milliers de chaines du monde entier * A 250 m à pied de la marina Fort Louis de Marigot * A 5 min à pied du centre ville de Marigot avec ses restaurants, boutiques et autres commerces * A 5 min de l'embarcadère pour Saint-Barth et Anguilla, et de la station de taxis

Aruba Private Resort. Its All Yours and Only Yours
Welcome to Casa Carmela. Relax in the resort sized pool and outdoor oasis. Melt the day away under the exotic palapas or toast your buns in the sun. Whatever your pleasure, Casa Carmella aims to please. She’s a short walk to Palm Beach one of the top rated beaches in the world. Restaurants, casinos and nightlife are walkable as well. She comes with a comfy king size bed, gas grill, fully equipped kitchen, beach chairs & beach towels and cooler. This is all yours and only yours.

Chalet De Los Vientos
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 💡

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.

Best location with pool, steps from beach!
Wake up in a luxurious king bed with premium bedding, gazing out at your private pool framed by lush palm trees. Start the day with breakfast from the fully equipped kitchen, then catch up online with blazing-fast Wi-Fi under the shaded pergola. Cool off in the pool or rinse in the outdoor hot shower before walking just 50 yards to San Juan’s best beach. Ideal for couples, solo travelers, remote workers, or small families seeking comfort and style.

Landhuis des Bouvrie Loft
When you walk through the gates of the courtyard of the Loft, you will enter a completely different, dream-like world. Silence, Nature, Space and Privacy are the keywords, when we try to describe what you will experience during a stay in our beautiful loft. A place where history and modern design come together. You will find yourself in a bare-foot-luxury bubble in space and time what will inspire you to slow down, completely surrounded by nature.

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)

Suite Magnolia, jacuzzi terapéutico sal,Monteverde
Bio Hábitat Monteverde te invita a vivir una experiencia única rodeada de bosque primario. Desde el balcón observa animales y disfruta del cielo estrellado en la Net. Relájate en nuestro jacuzzi de cristal con aguas de sal, mientras contemplas atardeceres inolvidables sobre la península de Nicoya. Un rincón exclusivo donde naturaleza, comodidad y bienestar se unen para regalarte un verdadero paraíso en Monteverde.
Popular amenities for West Indies rentals with a pool
House rentals with a pool

Modern Villa with Pool Minutes to Grace Bay Beach

The Green House Mint - Ocean View, Private Pool

Airstream With Pool, Amazing Ocean & Nature Views

B Luxury Ocean View, Heated Pool & Generator

Curated Luxury Retreat | Pool • Spa • 8 min Beach

Private Oceanfront luxurious city villa with pool

Casa Dalila - Luxury Home with Private Pool

La Casita: Private Heated Pool W/ Ocean Views
Apartment rentals with a pool

*NEW* Modern Ocean Breeze King Suite Infinity Pool

Luxe King Suite -valet parking-near beach

Wrap Around Balcony~Views~Pack your Bathing Suit!

Oceanfront 1BR Lux Apt Pool Beach Gym Pickleball

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

Beachfront Luxury @ Mar Chiquita

G38 Peaceful studio Oceanfront Punta Palmera

The Artist
Home rentals with a private pool

Sunbathe by a PrivatePool-Elegant House near beach

Casa El Camino Rustic Jungle Getaway with pool

Walk to the Beach From a Poolside Retreat in Sunset Crest

Gorgeous Colonial House near Cafes and Bars

Boutique House & Pool Next To The Best Palm Beach

Casa Pantheon Luxury Colonial House

Artistic Villa HC + Breakfast, Cleaning & Staff

Condado Beach Vistas by Cesar 2501
Destinations to explore
- Chalet rentals West Indies
- Rentals with an accessible-height toilet West Indies
- Island rentals West Indies
- Loft rentals West Indies
- Luxury rentals West Indies
- Pet-friendly rentals West Indies
- House rentals West Indies
- Container rentals West Indies
- Rentals with an accessible-height bed West Indies
- Hostel rentals West Indies
- Boutique hotels West Indies
- Tiny house rentals West Indies
- Smoking-friendly rentals West Indies
- Rentals with a patio West Indies
- Campsite rentals West Indies
- Private suite rentals West Indies
- Ski-in/ski-out rentals West Indies
- Bus rentals West Indies
- Waterfront rentals West Indies
- Rentals with a fireplace West Indies
- Rentals with beach access West Indies
- Bungalow rentals West Indies
- Boat rentals West Indies
- Holiday home rentals West Indies
- Rentals with a sauna West Indies
- Nature eco lodge rentals West Indies
- Hotel rooms West Indies
- Flat rentals West Indies
- Rentals with a cinema West Indies
- Earth house rentals West Indies
- Villa rentals West Indies
- Rentals with a hot tub West Indies
- Townhouse rentals West Indies
- Bed and breakfasts West Indies
- Rentals with a washing machine and dryer West Indies
- Aparthotel rentals West Indies
- Rentals with outdoor seating West Indies
- Castle rentals West Indies
- Cabin rentals West Indies
- Cottage rentals West Indies
- Guest house rentals West Indies
- Beachfront rentals West Indies
- Farm stay rentals West Indies
- Resort rentals West Indies
- Tipi rentals West Indies
- Rentals with a kayak West Indies
- Houseboat rentals West Indies
- Rentals with lake access West Indies
- Pension rentals West Indies
- Barn rentals West Indies
- Ranch rentals West Indies
- Rentals with an EV charger West Indies
- Rentals with breakfast West Indies
- Cave rentals West Indies
- Yurt rentals West Indies
- Dome rentals West Indies
- Apartment rentals West Indies
- Fitness-friendly rentals West Indies
- Treehouse rentals West Indies
- Motorhome rentals West Indies
- Tent rentals West Indies
- Rentals with a balcony West Indies
- Family-friendly rentals West Indies
- Serviced apartment rentals West Indies
- Rentals with a firepit West Indies




