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Vacation rentals with a pool in Caribbean

Find and book unique homes with a pool on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Caribbean rentals with a pool

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Guest favorite
A serene outdoor area features a vibrant blue swimming pool surrounded by natural stone tiles. Lush greenery lines the space, while rustic brick walls and open columns create a seamless connection to the interior. Comfortable seating is visible in the background.
Home in CARTAGENA
4.9 out of 5 average rating, 105 reviews

Casa Linda

Superhost
A sunny outdoor space features a large heated saltwater pool surrounded by lush palm trees and vibrant tropical plants. Comfortable lounge chairs are positioned poolside, accompanied by a small table. The tranquil setting offers an ideal space for relaxation and enjoyment.
Home in Miami
4.92 out of 5 average rating, 194 reviews

Private Pool and Tropical Garden Oasis

Guest favorite
A private plunge pool is surrounded by wooden decking, with a gentle waterfall feature adding a soothing sound. Lush green mountains and the turquoise bay are visible in the background, framed by colorful clouds at sunset.
Home in Culebra
4.97 out of 5 average rating, 145 reviews

Casa Anya @ Hilltop (private infinity plunge pool)

Top guest favorite
Home in San Nicolas
5 out of 5 average rating, 151 reviews

Ocean Front Family Vacation Home, at Baby Beach

Guest favorite
An infinity pool with tranquil water reflects the surrounding greenery and sky. A sun lounger in a natural tone is positioned beside the pool, offering a relaxing spot to enjoy the view. Wooden decking frames the pool area, enhancing the serene atmosphere.
Home in Sosúa
4.97 out of 5 average rating, 179 reviews

Casa Cascada

Top guest favorite
A private outdoor area features a swimming pool bordered by a tiled edge, with poolside loungers positioned nearby. The ocean view is unobstructed, with a pergola providing shade over the seating area. The sky is clear blue, and sunlight casts shadows on the patio.
Home in Willemstad
4.99 out of 5 average rating, 105 reviews

Villa Jeremi

Top guest favorite
A private pool is surrounded by vibrant greenery and palm trees, providing a tropical ambiance. Two wooden chairs with soft cushions sit at a small table, with clear water glistening in the pool. The ocean can be seen in the background, adding to the serene setting.
Home in Willemstad
4.95 out of 5 average rating, 159 reviews

Private Oceanfront luxurious city villa with pool

Top guest favorite
A private heated swimming pool is visible in the foreground, surrounded by tiled borders. Steps lead up from the pool to a two-story white house with multiple windows and balconies. Lush greenery and a white chair complement the outdoor space.
Home in Jayuya
4.97 out of 5 average rating, 373 reviews

Monte Niebla, a piece of heaven in the mountains

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Condo rentals with a pool

Top guest favorite
A serene courtyard is framed by two-story residential buildings, featuring a sparkling pool at the center. The pool is surrounded by sun loungers, with palm trees dotting the landscape, creating a calm and inviting space for relaxation.
Condo in Punta Cana
4.95 out of 5 average rating, 114 reviews

Precioso apartamento a 600 metros de la playa

Top guest favorite
A large pool area is visible, featuring multiple lounge chairs with orange cushions and umbrellas. The infinity pool merges with the horizon, offering unobstructed views of the sea at sunset. A serene atmosphere is created by the smooth water and open space surrounding the pool.
Condo in CARTAGENA
4.93 out of 5 average rating, 185 reviews

De Lujo Frente al Mar-Sector Turistico Bocagrande.

Superhost
The image features an outdoor area with a heated pool surrounded by lounge chairs and shaded seating. A dock extends into the water, offering access to the waterway. Lush greenery adds a sense of tranquility, enhancing the inviting atmosphere of the space.
Condo in Pompano Beach
4.82 out of 5 average rating, 303 reviews

ON CANAL! Pool+Walk to BEACH! Boat Watch! 2b/2b

Guest favorite
Condo in Punta Cana
4.92 out of 5 average rating, 123 reviews

Stunnishing Ocean View Penthouse with private pool

Top guest favorite
A beachfront view is presented from a spacious patio, featuring white railing and tropical palm trees swaying in the gentle breeze. The vibrant blue ocean waters are visible beyond the sandy beach, under a bright sky dotted with clouds.
Condo in Manatí
4.98 out of 5 average rating, 102 reviews

Beachfront Luxury @ Mar Chiquita

Top guest favorite
An aerial view of the resort features two infinity pools surrounded by a tropical deck. Lounge chairs are placed strategically around the pools, which are framed by lush greenery and palm trees. The nearby road and ocean can be seen in the background.
Condo in Noord
5 out of 5 average rating, 120 reviews

Aruba Oceanfront Top Floor Condo Eagle Beach

Superhost
Two high-rise condominium buildings are depicted, showcasing modern architectural design with expansive glass balconies. The foreground contains landscaped greenery, enhancing the outdoor space. The perspective offers a view of the surrounding urban landscape, set against a clear blue sky.
Condo in Miami
4.77 out of 5 average rating, 213 reviews

BEAUTIFUL 2BD ★ OVERLOOKING THE OCEAN ★BRICKELL

Top guest favorite
A tranquil pool reflects the surrounding architecture and clouds at sunset. Spacious lounging areas and palm trees enhance the serene environment, while the gleaming water invites relaxation. The modern buildings are positioned in the background, complementing the peaceful outdoor setting.
Condo in Punta Cana
4.99 out of 5 average rating, 163 reviews

G38 Peaceful studio Oceanfront Punta Palmera

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Home rentals with a private pool

Guest favorite
An inviting rooftop terrace features a hanging chair and comfortable cushioned seating. A wooden coffee table stands at the center. Lush greenery provides a natural backdrop with trees visible, and the sky showcases soft clouds, creating a serene outdoor atmosphere.
Home in Santo Domingo
4.94 out of 5 average rating, 411 reviews

Gorgeous Colonial House near Cafes and Bars

Top guest favorite
A heated saltwater pool is framed by lush greenery, providing a sense of privacy. The pool features a decorative wall at one end, adding an elegant touch. The surrounding patio offers a clean, open space for relaxation.
Home in West Palm Beach
4.96 out of 5 average rating, 172 reviews

Soak up the Beachy Vibe at a Vibrant Poolside Paradise

Guest favorite
An outdoor patio area is featured with a wooden dining table set for six, accompanied by lounge chairs. A sparkling pool is visible in the background, surrounded by lush greenery and the striking architectural elements of the home, including an aged stone wall.
Villa in Santo Domingo
4.93 out of 5 average rating, 342 reviews

Casa Pantheon Luxury Colonial House

Guest favorite
Bright art-filled space features high ceilings with wooden beams. Colorful paintings adorn the walls, drawing attention to the gallery-like atmosphere. A mix of wicker seating and wooden chairs is arranged around a central table, complemented by a vibrant vase and fresh flowers.
Villa in CARTAGENA
4.87 out of 5 average rating, 155 reviews

Old City Villa - Breakfast & Housekeeping Included

Guest favorite
A private pool sits surrounded by lush ferns and a stone wall, providing a tranquil setting. A patio area features a dining table under an umbrella, creating a space for outdoor relaxation. The pool's blue tiles reflect sunlight, enhancing the serene environment.
Townhouse in CARTAGENA
4.87 out of 5 average rating, 215 reviews

Walled City Luxurious Townhouse With Private Pool

Guest favorite
A panoramic view from a high-rise balcony captures the expansive coastline meeting the city's skyline. Various buildings, including modern high-rises and low-rise structures, line the streets, with the ocean stretching towards the horizon under a cloudy sky.
Condo in San Juan
4.9 out of 5 average rating, 265 reviews

Condado Beach Vistas by Cesar 2501

Guest favorite
A serene pathway lined with tropical plants leads to a stone table, surrounded by lush greenery and vibrant palms. The path is paved with bricks, creating a welcoming entrance to a private garden area.
Guesthouse in West Palm Beach
4.97 out of 5 average rating, 174 reviews

Tropical Cabana with Pool in West Palm Beach

Top guest favorite
An open living area features a spacious seating arrangement on a light-colored floor. The wooden table is centered among sofas adorned with colorful cushions. A view of the ocean and palm trees is visible through the large openings leading to the outdoor area.
Villa in Las Terrenas
5 out of 5 average rating, 67 reviews

Luxury Beach Front Villa with private pool

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