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Holiday 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 favourite
A thatched-roof tiki hut provides shade over a seating area, featuring a gray couch and glass coffee table. A hammock is suspended nearby, and a pool reflects the clear sky. The synthetic grass surrounds the area, contributing to a relaxed atmosphere.
Home in Hollywood
4.97 out of 5 average rating, 240 reviews

Hollywood Sunshine Resort Pool House w/ Hot tub

This amazing mini resort has been created with the ultimate comfort of our guests in mind. Enjoy a courtyard and pool deck designed with plenty of outdoor seating and a tiki hut. The property has synthetic grass through out, perfect for kids and family to sit and play on. Super fast Wifi. USB ports in the bedroom. Super comfortable bed. Smart Tv that you can Stream your favorite movies to. Washer/Dryer combo. Outdoor BBQ. Our home is located Minutes from downtown and Hollywood beach/ boardwalk.

Top Guest favourite
Loft in La Fortuna
4.97 out of 5 average rating, 199 reviews

Natural & Cozy Arenal Getaway

Un hospedaje para escapar de la rutina y conectar con la naturaleza, tiene un diseño moderno con una cálida decoración, rodeado de naturaleza donde podrás observar muchas aves, una linda vista al volcán, balcón, terraza, una refrescante piscina y jacuzzi privado. Un lugar ideal para parejas, amigos o para que puedas teletrabajar tranquilamente. Ubicados estratégicamente cerca de todas las actividades principales y a tan solo 2.5 km del centro de La Fortuna y a 1 km de La catarata La Fortuna.

Top Guest favourite
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, 110 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 favourite
A serene outdoor area features a sparkling pool surrounded by lush greenery and tropical plants. A shaded seating area is provided by a large umbrella, along with a cozy hanging chair in the background. The peaceful ambiance is enhanced by bright blue skies.
Guest suite in Luquillo
5 out of 5 average rating, 205 reviews

Casa Encanto Rainforest Retreat

This Guest Suite, on the lower level of our exclusive luxury villa, Casa Encanto, is the perfect tropical getaway. Nestled in the peaceful and lush foothills of the El Yunque Rain Forest, Located in Luquillo with many nearby attractions. You’ll have easy access to downtown Luquillo, El Yunque National Rainforest, Luquillo Beach, Caribali Adventure Park, Las Paylas, charter boat trips, snorkeling, zip lines and much more. The Guest Suite is fully solar with Tesla Batteries and backup water

Top Guest favourite
A serene view of the turquoise ocean stretches beyond a well-maintained pool area. Lush palm trees and vibrant greenery frame the space, with a sandy beach visible nearby. The outdoor seating area is partially shaded, creating a relaxing atmosphere for guests.
Holiday home in Bodden Town
5 out of 5 average rating, 103 reviews

Art Beach House, boutique style luxury.

Private getaway for couples or singles perfect for honeymooners situated at beautiful frank sound. 25 mins from George town so car essential, many attractions nearby include the crystal caves 5 mins botanical gardens and rum point, and the beautiful east end. we also boast some of the the best dining on island. So lots to do or just chill on your private beach away from the crowds. the apartment is situated on ground floor level with art studio/Gallery above. with exclusive use of pool,

Top Guest favourite
The image showcases an aerial view of the Eco-friendly Airstream RV surrounded by a lush cactus landscape, with a deck and a private saltwater pool. The Caribbean Sea is visible in the background, emphasizing the tranquil natural setting.
Home in Paradera
5 out of 5 average rating, 212 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 favourite
The studio features an airy living space with air conditioning and a kitchenette. A small dining table with two chairs is positioned near the large window, which opens to a balcony overlooking lush greenery. Natural light fills the room, enhancing the inviting atmosphere.
Apartment in Willemstad
4.99 out of 5 average rating, 105 reviews

Charming 2p. poolside studio in vibrant Pietermaai

Stay in this lovely and peaceful studio in the middle of vibrant Pietermaai. Enjoy the elegance of this UNESCO world heritage site Willemstad on the beautiful Dutch Caribbean Island Curacao from your doorstep. You will be staying between the charming, colorful painted monuments. Pietermaai offers restaurants, bars, shops, a diving school and the most beautiful sunsets on walking distance. The studio itself is on a quiet, car-free alley, fully airconditioned, and offers pool access.

Top Guest favourite
A wooden cabin is set within a lush landscape, featuring open double doors that reveal a cozy seating area. Comfortable benches are positioned on a wooden deck, surrounded by greenery. A pathway made of stepping stones leads towards the entrance, enhancing accessibility.
Place to stay in Río Grande
4.98 out of 5 average rating, 273 reviews

Glamping at Relaxing Atmosphere In Nature

Glamping at Relaxing Atmosphere In Nature (RAIN) provides a serene and private getaway where you can relish the magic of the rainforest, with the calming sounds of rain, birds, and the Coqui's call. Our latest cabin is outfitted with all the comforts to ensure your glamping experience is unforgettable. Comfortably immerse yourself in the forest's flora and fauna. Escape the bustle of modern life and unwind. We embrace and celebrate diversity; all are welcome!

Top Guest favourite
Treehouse in Laborie
4.96 out of 5 average rating, 181 reviews

Bay Treehouse • Private Pool • Near Beach

A distinctive, elevated hideaway in an authentic St Lucian village, Bay Treehouse sits just back from Laborie Beach — with its own private plunge pool and made for effortless island chill. Built largely from local wood, it’s designed for sea breezes and the easy rhythm of island life, with a fully air-conditioned bedroom for cool, comfortable nights. Guests love its privacy, character and connection to village life — and many stay for their entire trip.

Top Guest favourite
A vibrant coastal view is framed by lush green foliage, showcasing calm turquoise waters under a clear blue sky. Gentle waves are seen lapping at the shore, with distant hills creating a serene backdrop against the horizon.
Apartment in East End
4.96 out of 5 average rating, 208 reviews

Waterfront Cottage, St. Croix US VI

"30 Steps to Paradise" Sweet and cool 1-bedroom cottage with large porch attached to a family home, with complete privacy. Hear the sound of the waves and walk to several beaches. Located near Jack's Bay on the south east tip of the island. The cottage has ceiling fans, no air-conditioning. The pool is available for guests. The other name for the cottage is "30 steps to Paradise" because it has 30 steps from the road to the entrance of the cottage.

Top Guest favourite
A colorful hammock is suspended between two palm trees, inviting relaxation beside a sparkling pool. Lush tropical plants surround the outdoor area, creating a peaceful ambience. The inviting pool area is visible in the background, enhancing the serene outdoor setting.
Guest suite in Homestead
4.99 out of 5 average rating, 178 reviews

“Have Fun at Hacienda Paraíso” Suite 1 | pool |

Welcome to Room 1, the first addition at Hacienda Paraíso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.

Top Guest favourite
Villa in La Fortuna
4.98 out of 5 average rating, 181 reviews

Villa Mano de Tigre, A Volcano in your Garden!

The vacation villa with the closest and most SPECTACULAR view of the Arenal Volcano 10 minutes to downtown La Fortuna Fully equipped Private hot tub Grill and fire pit area Optic fiber high speed Wi-Fi Located 1.5 kilometers from the main road at the top of a private hill where you will be surrounded by flora and fauna. All guests can enjoy the 1-day pass to the nearby resort's hot springs Base rate for 2 people. Vehicle recommended

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