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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 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 bright bedroom is featured, showcasing a spacious bed adorned with soft pillows. Large windows provide panoramic views of the bay, allowing natural light to illuminate the area. A ceiling fan enhances airflow, while modern furnishings add to the inviting atmosphere.
Apartment in Montego Bay
4.95 out of 5 average rating, 147 reviews

Oceanfront 1BR Lux Apt Pool Beach Gym Pickleball

Discover the ultimate tropical retreat at the Soleil Residences, where luxury meets serenity. This elegant oceanfront one-bedroom condominium features a stunning balcony with 180-degree views of the Bay, inviting you to bask in the beauty of Jamaica's coastline. Highlights - Lge Waterfront Pool & Pool Deck * Private Beach Access * Gym * Tennis/Pickleball* Kids Play Area * Gated Community * Fast Fibre WiFi* Chef on request * Spa Services * Concierge Services * Full Time Driver Upon Request

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, 211 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
An aerial view showcases a swimming pool with a circular hot tub nearby, surrounded by a paved patio. Several lounge chairs are positioned under a shaded gazebo, with expansive views of the Atlantic Ocean and sandy beaches visible in the background.
Home in Isabela
4.98 out of 5 average rating, 328 reviews

Caribbean Paradise I

This is a studio on a cliff with a spectacular view facing mangroves, Middlesex and Poza El Teodoro beaches and the Atlantic Ocean. Each studio has Smart TV internet, private bathroom, kitchenette microwave, electric coffee maker, small refrigerator, queen size bed, side table, futon (convertible to twin size bed), AC and a balcony with ocean view. The common areas for the studios are a pool, gazebo, sitting area by the pool and they all have ocean view. Pets are not allowed.

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, 272 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
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.
Flat 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 serene outdoor area features a small plunge pool surrounded by a deck. Lounge chairs are positioned nearby under the shade of a tree, with lush greenery creating a natural backdrop. The clear blue water reflects the bright sky, enhancing the tranquil setting.
Barn in Willemstad
4.95 out of 5 average rating, 152 reviews

Bouvrie Loft Country House

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.

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
An outdoor seating area is showcased, featuring two cushioned armchairs and a wooden coffee table. The space offers views of lush greenery and a pool below, framed by a wrought iron railing. Bright skies and distant hills enhance the tranquil ambiance.
Flat in Cruz Bay
5 out of 5 average rating, 169 reviews

Sieben Apartment * Pool* next to Hiking trails

Spacious Luxury 2 Bedroom, 2 bathroom apartment with fully equipped kitchen and washer/dryer. Both rooms have memory foam mattresses from Loom & Leaf. The master bedroom has 1 King bed with private bathroom, and the second bedroom can be set up as 2 Twin beds or 1 King bed. 10 min drive from Cruzbay, Restaurants and grocery Stores. Shared brand Pool (4ft deep) with two other apartments. Shared BBQ by the Pool.

Top guest favourite
Treehouse in Monteverde
4.99 out of 5 average rating, 185 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.

Top guest favourite
A private pool with clear blue water and steps leading in is surrounded by tropical plants. A shaded area with a patio can be seen in the background, along with a door that opens into the interior space.
Tiny home in Aguada
4.98 out of 5 average rating, 189 reviews

Private Beach House/Private Pool/Heated

Relax in this stylish, quiet space. Steps to historic Cañones de Aguada Beach. Enjoy the beautiful private pool with your partner. Fall in love with the beautiful poolside gardens while preparing your favorite charcoal dishes in the BBQ area. Close to one of the best gastronomic routes in the western area with a beautiful coastline. It will be an unforgettable experience...

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