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.

1 of 1 pages1 / 1

Top Guest favourite

A charming cabin crafted from natural materials is positioned atop a wooden structure. A thatched roof provides shade, while large glass doors invite light. A pool is visible in the foreground, reflecting the blue sky and surrounding greenery.

Cabin in Isabela

4.99 out of 5 average rating, 291 reviews

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.

LocationFamilyBreakfast

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

5.0 out of 5 average rating, 140 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.

LocationValueComfort

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 Getsemany

4.99 out of 5 average rating, 126 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.

LocationValueCondition

Top Guest favourite

A modern oceanfront chalet is visible, featuring a pool surrounded by a patio. White lounge chairs and a wooden table are arranged nearby. The structure showcases a spacious design with large windows and a colorful mural. Lush greenery frames the area under a bright blue sky.

Chalet in Puerto Nuevo

4.95 out of 5 average rating, 304 reviews

“CASA ROARK” is a one-of-a-kind oceanfront chalet.

“CASA ROARK” IS A ONE-OF-A-KIND OCEANFRONT CHALET WITH VIEWS THAT CAN EASILY BE AMONG THE MOST BEAUTIFUL WORLDWIDE. IT IS ONLY A FEW STEPS FROM THE BEACH. THE RECENTLY REMODELED CHALET HAS 4 BEDROOMS, ALL WITH A/C AND 65"TVS; THE 1st MASTER ROOM HAS A KING-SIZE BED AND A TWIN SOFA BED, THE 2nd MASTER BEDROOM HAS A QUEEN SIZE BED, THE 3rd HAS 2 BUNK BEDS AND THE 4th ROOM HAS TWO TWIN SIZE BEDS. YOU HAVE A BEAUTIFUL HEATED POOL OVERLOOKING THE OCEAN. POOL USE IS ONLY FOR OUR GUESTS.

FamilyValueBeach

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

5.0 out of 5 average rating, 104 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

ValueFamilyParking

Luxe

The villa is surrounded by lush greenery, featuring a spacious pool area with comfortable loungers. A serene atmosphere is created by the natural light filtering through the trees, while the modern design of the villa complements the tranquil jungle setting.

Villa in Tulum

4.97 out of 5 average rating, 106 reviews

Villa Arthur 600 · 9 Guests · Permanent staff

Villa Arthur 600 is a luxurious private villa with permanent staff, ideally located near La Veleta, Gypsea Market, and downtown access. Perfect for 9 guests, the villa features a spacious pool, master suites with tubs overlooking the pool, a large living room with a professional kitchen, a dining table for 10, and comfortable sofas. Enjoy a large park and a rooftop with BBQ. With daylight surveillance to ensure safety. Daily breakfast is available at an extra cost.

LocationValuePool

Top Guest favourite

A serene outdoor living space features comfortable seating arranged around a low table, with panoramic views of a sunset over lush greenery. An infinity pool reflects the vibrant colors of the sky, framed by large glass doors that open to the natural surroundings.

Home in Monte Verde

4.97 out of 5 average rating, 109 reviews

Luxury villa & Infinity Pool

Immerse yourself in tranquility and natural beauty with this spectacular house in the middle of the forest, designed to offer you a unique experience of luxury and relaxation. This property combines modern elegance with the charm of nature. Wake up to the sounds of the forest and enjoy the peace that only this natural setting can provide. The house offers total privacy, but is located in the heart of Monteverde, a short drive away from local restaurants and shops.

FamilyValueBarbecue

Top Guest favourite

Home in Venecia

4.97 out of 5 average rating, 218 reviews

La Ceiba, Modern Villa with Pool in Dairy Farm

Quinta La Ceiba is in heart of a dairy farm, surrounded by green pastures, cows, and mountain views. Enjoy sunrises and sunsets from this 3-bedroom house. Features include a fully equipped kitchen, very comfortable beds, and outdoor dining plus a living room with a hanging bench, perfect for relaxing and enjoy the nature surrounding it, ideally located between Bajos del Toro and La Fortuna with endless nearby adventures. Inquire about the private chef service.

ValueLocationSleep quality

Luxe

A serene rooftop pool area is surrounded by lush greenery and decorative stone walls. A comfortable lounge area with soft cushions invites relaxation, while sunlight reflects off the clear water, creating a tranquil atmosphere. The open space allows for easy movement and enjoyment of the outdoors.

Loft in Tulum

4.99 out of 5 average rating, 138 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!

FamilyLocationCondition

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, 615 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.

LocationFamilyTV

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, 198 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

LocationFamilyComfort

Top Guest favourite

The image captures a serene oceanfront setting, featuring a magnesium pool that reflects the warm sunset. Lush greenery borders the pool area, with palm trees framing the scene, creating a peaceful atmosphere. The calm sea is visible beyond the pool's edge.

Villa in St. Willibrordus

4.91 out of 5 average rating, 131 reviews

Villa Yazmin - Ocean Front Villa

Follow us @villa_yazmin_curacao Experience refined luxury with stunning ocean views. A beautiful piano for serene moments, a magnesium pool gentle on body and skin, and elegant bedrooms each with a private bathroom. A fully equipped kitchen with cappuccino machine and Quooker. Car rental, early check in and late check out available upon request. Please contact Mary in advance for personalized arrangements. Warm greetings, Villa Yazmin Mary

FamilyLocationAmenities