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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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Guest favourite
A striking A-frame house is illuminated at night, showcasing its wooden exterior and large glass front doors. Lush greenery and neatly arranged stones adorn the pathway leading up to the entrance, while subtle lighting enhances the surrounding landscape.
Cabin in Aguadilla
4.97 out of 5 average rating, 151 reviews

Blackandwoodcabin Cabin/ chalet in Aguadilla

Cualquier actividad privada, reunión, celebración, fiesta, boda, recepción o evento similar está sujeto a cargos adicionales y debe coordinarse con antelación. Es imprescindible obtener la aprobación previa por escrito de la administración. Los eventos no autorizados están estrictamente prohibidos. Piscina de agua salada, jacuzzi. Un cuarto con tina . Un cuarto con sofá cama y televisor. Cocina completa, microondas. Lavadora y secadora. Planta eléctrica, cisterna de agua. Iluminación nocturna .

Top Guest favourite
An outdoor space features a private pool surrounded by lush tropical foliage. A comfortable lounge area with a hammock is nestled beside the pool, offering a serene retreat. Natural wood decking enhances the tranquil ambiance, while sunlight filters through the greenery, creating playful patterns on the surface.
Apartment in Tulum
4.97 out of 5 average rating, 126 reviews

Mayan-Inspired Luxe Villa & Concierge| 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
An infinity pool stretches along the edge of the property, with mountain and ocean views. A wooden deck is lined with tropical plants, and modern architectural elements are highlighted by warm sunset hues. Inside, the kitchen and dining area are visible through expansive glass doors.
Villa in Playa Bejuco
4.98 out of 5 average rating, 141 reviews

Modern Villa+Private Pool+Ocean View+Gated+Beaches

This modern and secluded jungle paradise is surrounded by 40 acres of lush tropical forest with magnificent mangrove and ocean views, less than one kilometer away from one of the most stunning beaches in Costa Rica! The villa has a private pool, BBQ, and a fully equipped 2-bedroom guest house. The property is located 2 hours from San Jose's Juan Santa Maria International Airport (SJO), close to 3 National Parks: Manuel Antonio, Carrara, and Cangreja, with several restaurants and a market nearby.

Top Guest favourite
A wooden terrace is shown with a stool positioned near the railing. The sun rises above a distant landscape, casting warm light over lush green hills and the ocean. An infinity pool is visible nearby, blending beautifully with the scenic surroundings.
Tiny home in Fajardo
4.99 out of 5 average rating, 293 reviews

Magical! Ocean view Cabana w/ Pool Spa on mountain

This memorable place is anything but ordinary. You will get to enjoy this amazing and super private space surrounded by nature and unbelievable views of the ocean and the city. Fully equipped with everything you will need during your stay to include kitchen, full bath with rain shower, A/C, living space with 55" TV, dinning and sleeping areas, terrace with killer views, and of course the pool spa with infinity view! And many more. All of this while enjoying of a complementary bottle of Wine!

Top Guest favourite
A rooftop terrace is captured at sunset, revealing a serene plunge pool surrounded by lush greenery. Solar panels adorn one side, while two loungers and a wooden table provide a relaxing outdoor space overlooking the jungle scenery.
Place to stay in Playa del Carmen
4.99 out of 5 average rating, 122 reviews

Strelitzia Skyloft Rooftop, Cenote & Infinity Pool

@thestrelitziaproject 🏆 The highest rated Airbnbs in Playa! ⭐️ The entire rooftop of this luxury home worth $1m+ is private for you! There is a reason generic apartments in town cost $70usd. Skyloft is unique. Your rooftop overlooks a stunning natural cenote and infinity pool. Climb the ladder to “The Perch” & enjoy incredible views over the jungle canopy as the sun sets. Experience a perfect nights sleep on our exquisite bamboo memory foam bed! We also offer stress free car rental!

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, 202 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, 101 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
A modern sanctuary is showcased amidst lush tropical foliage, featuring an inviting plunge pool. The structure's open design highlights floor-to-ceiling glass walls, allowing natural light to fill the interior. A vibrant sunset sky adds warmth to the scene, enhancing the tranquil surroundings.
Villa in Mal Pais
4.97 out of 5 average rating, 151 reviews

House of the Earth and the Sea - stunning luxury

Escape to La Casa Tierra y el Mar: A romantic luxurious mountain top sanctuary where architecture meets wilderness in Costa Rica's Nicoya Peninsula. Breathtaking ocean views, plunge pool, and wildlife at your doorstep. Gourmet kitchen, indoor outdoor living. Moments from pristine beaches, this architectural marvel offers the perfect blend of privacy, comfort, and adventure. Your secure and completely private tropical dream retreat awaits—where extraordinary design meets untamed nature.

Top Guest favourite
A cozy chalet is nestled in a lush green landscape, featuring a red roof and warm yellow exterior. A private heated pool is visible, surrounded by a wooden deck, and scenic hills are seen in the background under a colorful sunset.
Chalet in Caguas
4.99 out of 5 average rating, 192 reviews

Chalet De Los Vientos (Chalet of the Winds)

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 💡

Top Guest favourite
A tranquil swimming pool is framed by palm trees and a rocky outcrop, with clear blue water inviting relaxation. The ocean is visible in the background, where waves gently meet the shore. Lounge chairs are arranged around the pool area, creating a serene atmosphere.
Guest suite in George Town
4.98 out of 5 average rating, 268 reviews

Paradise Escape-Charming Oceanfront Guest Suite

A tranquil oceanfront escape for couples and solo adventurers... Wake-up in bed to a lovely view of a luscious green landscape that melds with the emerald green and blue ocean, sip a hot cup of coffee on the porch, enjoy a sunset cocktail by the ocean front pool, break a sweat in a friendly game of tennis, or take a blanket out to the lawn under the palm trees for breathtaking star gazing. PLEASE NOTE: WE ARE NOT LOCATED ON BATS CAVE BEACH. AIRBNB HAS THIS WRONG!

Top Guest favourite
An infinity pool extends toward the horizon, reflecting the blue sky above. Lush greenery borders the pool area, leading to a serene beach and ocean view. The landscape features gentle hills in the distance, completing this tranquil coastal scene.
Apartment in Tamarindo
4.98 out of 5 average rating, 273 reviews

Upper Casita Catalina in Tamarindo w Great Views

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 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 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, 568 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.

Popular amenities for Caribbean Sea rentals with a pool

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