Book the Best Hotels with POOL in Caribbean Islands in 2026 | Expedia.ca

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Check availability on Caribbean Islands Hotels with a Pool

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Sep 27 - Sep 28

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Sep 28 - Sep 29

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Our top choices for Caribbean Islands hotels with a pool

A resort with a large pool, palm trees, and a view of the ocean.

A spacious lobby with a high ceiling, large windows offering views of palm trees, and a seating area with modern furniture.

A beach with palm trees and chairs facing the ocean.

A balcony with a table, a bowl of oranges, a drink, and sunglasses.

1. Hyatt Vacation Club at Hacienda del Mar, Dorado

Sabana

Splash into blissful relaxation at this beachfront resort with outdoor pools and a poolside bar.

CA $169

CA $245 total

includes taxes & fees

Oct 19 - Oct 20

A resort with a water park, multiple swimming pools, and beachfront views.

A modern hotel room with a bed, sofa, two tables, and decorative wall art.

A modern living room with a sofa, ottoman, round table, and chairs.

2. Serenade Caribe Club Family Beach Resort – All Inclusive

Punta Cana

CA $242

CA $309 total

includes taxes & fees

Sep 30 - Oct 1

A resort pool area with lounge chairs, umbrellas, and a view of the ocean.

A bar area with a stone counter, wooden stools, and a view of the ocean at dusk.

A dining area with a large table and chairs, a wine rack, and a view of greenery through a glass wall.

A four-poster bed with a canopy, a nightstand with a lamp, wicker stools, and a view of a pool and greenery.

3. Coyaba Beach Resort

Montego Bay

CA $234

CA $333 total

includes taxes & fees

Oct 1 - Oct 2

A multi-story building with a pool, surrounded by lush greenery and palm trees.

A balcony with two chairs and a table, overlooking a coastal view with buildings and a clear sky.

A gated entrance with palm trees, a dirt path, and a view of the sea at sunset.

A beach with clear turquoise water, sandy shore, and palm trees.

4. Sea Gate Hotel

Isabel II

Splash into paradise at this hotel's sun-soaked pool sanctuary with refreshing views and aquatic adventures nearby.

CA $132

CA $153 total

includes taxes & fees

Oct 28 - Oct 29

A rooftop pool area with lounge chairs and umbrellas, a clear sky, and a view of the city skyline.

A modern hotel room with a large bed, a flat-screen TV, and a city view through floor-to-ceiling windows.

A buffet table with various food items and a view of the ocean.

A modern bathroom with a freestanding bathtub, a toilet, and a shower area.

5. Mauad Hotel Boutique

Gascue

CA $117

CA $150 total

includes taxes & fees

Oct 5 - Oct 6

A rooftop pool with glass railings, a view of the cityscape, and a clear sky.

A modern hotel room with a bed, sofa, and armchair, a TV, and a large window with a city view.

A spacious balcony with a city view, furnished with sofas, chairs, and tables.

A modern bar area with a central island, bar stools, and hanging plants.

6. Hyatt Centric Santo Domingo

Piantini

Rooftop pool retreat in Santo Domingo offers cooling respite and panoramic city views just minutes from Blue Mall.

CA $167

CA $214 total

includes taxes & fees

Oct 16 - Oct 17

A resort with multiple buildings, a central pool area, and surrounding greenery.

A spacious indoor area with a modern design, featuring a long corridor with seating and potted plants.

A lobby with artificial trees, a central spiral sculpture, and modern seating.

7. Lopesan Caoba Lagoon Resort Spa & Casino - All Inclusive

Bávaro

CA $418

CA $535 total

includes taxes & fees

Oct 27 - Oct 28

A resort with a swimming pool, palm trees, and a beach view.

An aerial view of a beach with rows of palm trees and sun loungers.

A spacious lobby with a high ceiling, polished marble floors, and modern furnishings including sofas and chairs.

A modern restaurant with round tables, grey chairs, and a dark interior.

8. Wyndham Alltra Punta Cana All-Inclusive Resort

Uvero Alto

CA $222

CA $222 total

includes taxes & fees

Sep 29 - Sep 30

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Choose what matters most at hotels with a pool in Caribbean Islands

Breakfast included

4 stars

5 stars

Hot tub

Spa

Hotels with pools and free breakfast in Caribbean Islands

A rooftop garden with four canopy beds, surrounded by lush tropical plants and palm trees under a clear blue sky.

A modern dining area with round tables, chairs, and potted plants.

A modern living room with a sectional sofa, a round coffee table, and a desk area with two computers.

A pool area with lounge chairs, umbrellas, and a small garden.

Hodelpa Garden Court

Punal

CA $170

CA $218 total

includes taxes & fees

Sep 28 - Sep 29

A modern hotel lobby with a reception desk, seating area, and a bar.

A person relaxing by a pool with a drink and a bowl of fruit.

A dining area with a table, chairs, a potted plant, and a view of tropical plants outside.

A modern living room with a sofa, a dining area, and a TV.

Hyatt Place Bayamon

Hato Tejas

CA $203

CA $260 total

includes taxes & fees

Sep 28 - Sep 29

A modern building with a bridge over a small pond, surrounded by lush greenery and palm trees.

A spacious lobby with large windows, blue seating, and a modern design.

A modern lobby with a large, glittery whale sculpture, a blue wave design, and a sign indicating a smoking area.

A spacious lobby with a classic car exhibit, modern furniture, and large windows offering natural light.

Costa Bahia Hotel & Convention Center

Guayanilla

CA $136

CA $163 total

includes taxes & fees

Oct 28 - Oct 29

A modern pool area with a view of mountains, a wooden staircase, and a glass railing.

An outdoor dining area with wooden tables and chairs, a ceiling fan, and decorative wall art.

A spacious outdoor dining area with wooden tables and chairs, covered by a wooden roof structure.

An aerial view of a beach with clear turquoise waters, a sandy shore, and a few people. There are trees and a building with a white roof in the background.

Ocean Winds Hotel

Costambar

CA $99

CA $127 total

includes taxes & fees

Sep 28 - Sep 29

A resort with a water park, multiple swimming pools, and beachfront views.

A modern hotel room with a bed, sofa, two tables, and decorative wall art.

A modern living room with a round wooden table, two upholstered chairs, a sofa, a TV mounted on a wooden wall, and a small kitchen area with a coffee machine.

A modern living room with a sofa, ottoman, round table, and chairs.

Serenade Caribe Club Family Beach Resort – All Inclusive

Punta Cana

CA $242

CA $309 total

includes taxes & fees

Sep 30 - Oct 1

A person relaxing by a pool with a tray of fruit and a drink.

A man sitting on a wicker sofa, reading a book, with a glass of drink on a table in front of him.

A modern hotel lobby with a reception desk, decorative white panels, and a buffet area with various food items.

A pool table with chairs, a bar area, and a seating area with plants and a wooden ceiling.

Hodelpa Gran Almirante Hotel & Casino

Los Jardines

CA $189

CA $242 total

includes taxes & fees

Sep 28 - Sep 29

A modern restaurant with large windows offering a city view.

A modern living room with a sofa, wicker chairs, a round coffee table, and a large window with curtains.

A spacious lobby with wooden beams, comfortable seating, and a bar area.

A breakfast table with various dishes, drinks, and utensils.

Dominican Fiesta Hotel

Los Cacicazgos

CA $127

CA $163 total

includes taxes & fees

Oct 5 - Oct 6

A spacious lobby with high ceilings, wooden furniture, and potted plants.

A wooden deck with a pergola, surrounded by tropical plants and rocks.

A nighttime pathway with evenly spaced lights leading to a building with a balcony.

A bedroom with a wooden bed, a bedside table with a lamp, an air conditioner, and a wall-mounted shelf with decorative items.

Hacienda Villa Sotomayor

Adjuntas

CA $90

CA $111 total

includes taxes & fees

Sep 28 - Sep 29

A spacious lobby with a marble reception desk, a potted plant, and a modern staircase.

A hotel room with a bed, white bedding, a potted plant, a wall-mounted device, and a painting on the wall.

A modern interior with a round ottoman, a small round table, and several potted plants.

A two-story building with balconies, a yellow facade, and a sign for 'PONCE PLAZA HOTEL & CASINO'.

Ponce Plaza Hotel & Casino

Ponce Centro

CA $177

CA $214 total

includes taxes & fees

Sep 28 - Sep 29

A modern cafe with wooden tables, green carpeting, and a kitchen area.

A hotel entrance with a sign reading 'spark by Hilton,' a covered area with lights, and a bench.

A house with a red and white exterior, a flag, and a flag-adorned chair.

A swimming pool with blue lounge chairs, a covered area, and a building with a red-tiled roof.

Spark by Hilton Ponce

Ponce

CA $173

CA $188 total

includes taxes & fees

Oct 4 - Oct 5

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4-star hotels with pools in Caribbean Islands

A rooftop garden with four canopy beds, surrounded by lush tropical plants and palm trees under a clear blue sky.

A modern dining area with round tables, chairs, and potted plants.

A modern living room with a sectional sofa, a round coffee table, and a desk area with two computers.

A pool area with lounge chairs, umbrellas, and a small garden.

Hodelpa Garden Court

Punal

CA $170

CA $218 total

includes taxes & fees

Sep 28 - Sep 29

A resort with a water park, multiple swimming pools, and beachfront views.

A modern hotel room with a bed, sofa, two tables, and decorative wall art.

A modern living room with a round wooden table, two upholstered chairs, a sofa, a TV mounted on a wooden wall, and a small kitchen area with a coffee machine.

A modern living room with a sofa, ottoman, round table, and chairs.

Serenade Caribe Club Family Beach Resort – All Inclusive

Punta Cana

CA $242

CA $309 total

includes taxes & fees

Sep 30 - Oct 1

A modern pool area with a view of mountains, a wooden staircase, and a glass railing.

An outdoor dining area with wooden tables and chairs, a ceiling fan, and decorative wall art.

A spacious outdoor dining area with wooden tables and chairs, covered by a wooden roof structure.

An aerial view of a beach with clear turquoise waters, a sandy shore, and a few people. There are trees and a building with a white roof in the background.

Ocean Winds Hotel

Costambar

CA $99

CA $127 total

includes taxes & fees

Sep 28 - Sep 29

A wooden deck with a table and chairs, overlooking a body of water and a distant island.

An overwater bungalows connected by a wooden walkway, a beach, and a resort building in the background.

A modern hotel room with a bed, a sofa, a TV, a minibar, and a view of the ocean.

A hotel room with a bed, a desk with a TV, a table with a chair, and a view of the outdoors.

Princess Senses The Mangrove Resort - Adults Only

Green Island

CA $728

CA $728 total

includes taxes & fees

Sep 29 - Sep 30

A spacious outdoor area with wooden flooring, seating arrangements, and a view of the beach.

A resort with multiple swimming pools, a beach, and a view of the ocean.

A resort with multiple buildings, a large pool area, and a beach.

A spacious dining area with wooden tables and chairs, hanging wicker chandeliers, and a high wooden ceiling.

Princess Grand Jamaica Resort - All Inclusive

Green Island

CA $652

CA $652 total

includes taxes & fees

Oct 27 - Oct 28

A modern restaurant with large windows offering a city view.

A modern living room with a sofa, wicker chairs, a round coffee table, and a large window with curtains.

A spacious lobby with wooden beams, comfortable seating, and a bar area.

A breakfast table with various dishes, drinks, and utensils.

Dominican Fiesta Hotel

Los Cacicazgos

CA $127

CA $163 total

includes taxes & fees

Oct 5 - Oct 6

A living room with a dark sofa, a coffee table, a TV mounted on the wall, and a wooden ceiling.

A dining area with a glass table and wooden chairs, a kitchen with dark cabinets, and a large mirror.

A doorway leading to a balcony with a view of a garden, a pool, and a yellow building.

A yellow building with a green roof, a wooden porch with chairs, and a number '21' on the door.

El Oasis Hotel

Aguada

CA $104

CA $113 total

includes taxes & fees

Oct 19 - Oct 20

A spacious living area with a large window, a sofa set, a coffee table, and a view of a building and palm trees.

A modern hotel with a central pool, multiple floors, and a rooftop terrace.

A modern kitchen with a central island, bar stools, and pendant lighting.

A modern hotel room with a large bed, a desk, and a balcony with a view of the building's exterior.

Faranda Single 1 Punta Cana Adults Only

Punta Cana

CA $161

CA $207 total

includes taxes & fees

Oct 27 - Oct 28

A large swimming pool with a castle-like structure in the center, surrounded by lounge chairs and umbrellas.

A beach resort with multiple levels of buildings, palm trees, and a clear view of the ocean.

A hotel lobby with a view of a castle, seating areas, and a ceiling fan.

A resort with multiple buildings, a beach, and palm trees.

Bahia Principe Explore Legend - Hyatt Inclusive Collection - All Inclusive

Bávaro

CA $356

CA $356 total

includes taxes & fees

Sep 28 - Sep 29

A rooftop pool area with lounge chairs and a waterfall feature.

A modern hotel room with a sofa, a dining table, a TV, and large windows offering city views.

A multi-story hotel with a modern design, featuring balconies and large windows.

A bar area with wooden furniture, a counter, and a TV screen displaying a sports event.

W&P Santo Domingo

Bella Vista

CA $154

CA $197 total

includes taxes & fees

Oct 10 - Oct 11

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5-star hotels with pools in Caribbean Islands

A person relaxing by a pool with a tray of fruit and a drink.

A man sitting on a wicker sofa, reading a book, with a glass of drink on a table in front of him.

A modern hotel lobby with a reception desk, decorative white panels, and a buffet area with various food items.

A pool table with chairs, a bar area, and a seating area with plants and a wooden ceiling.

Hodelpa Gran Almirante Hotel & Casino

Los Jardines

CA $189

CA $242 total

includes taxes & fees

Sep 28 - Sep 29

A resort with a central pool, multiple lounge areas, and a beach.

A beach resort with a white sandy beach, clear turquoise water, and a row of white buildings with balconies overlooking the beach.

A spacious lobby with a grand chandelier, multiple levels with columns, and a central staircase.

A hot tub with a wooden deck and a view of the beach.

Grand Palladium Jamaica Resort & Spa All Inclusive

Lucea

CA $410

CA $477 total

includes taxes & fees

Sep 29 - Sep 30

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building in the background.

A spacious lobby with a seating area, a bar, and large windows offering views of the outside.

An aerial view of a resort with multiple buildings, a large pool, and a beach area with palm trees.

A beachside resort with outdoor seating areas, palm trees, and a thatched-roof structure.

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

Bávaro

CA $359

CA $460 total

includes taxes & fees

Oct 27 - Oct 28

A resort with multiple swimming pools, sun loungers, and a view of a forested hill.

An aerial view of a beach with rows of sun loungers and umbrellas, and a clear view of the ocean.

A modern outdoor patio with a black and white tiled floor, a wooden ceiling, and a view of the ocean.

A modern hotel room with a large bed, a balcony with a view of the sea, and a ceiling fan.

Ocean Coral Spring - All Inclusive

Falmouth

CA $471

CA $525 total

includes taxes & fees

Oct 21 - Oct 22

A poolside area with lounge chairs and umbrellas, a clear sky, and a view of the ocean.

A spacious lobby with a high ceiling, a central staircase, and a seating area with sofas and chairs.

A restaurant with round tables, yellow tablecloths, and a view of the ocean.

An outdoor seating area with multiple chairs and tables, surrounded by potted plants and a view of the ocean.

Catalonia Santo Domingo

Ciudad Universitaria

CA $147

CA $188 total

includes taxes & fees

Oct 4 - Oct 5

A resort pool with clear blue water, surrounded by palm trees and lounge chairs, with a view of the ocean and modern buildings in the background.

A spacious living area with a view of the ocean, featuring a sofa, chairs, a coffee table, and pendant lighting.

A balcony with a view of the ocean, featuring lounge chairs and a patterned floor.

A spacious lobby with a high ceiling, large windows, and a central seating area.

Ocean Eden Bay - Adults Only - All inclusive

Falmouth

CA $639

CA $639 total

includes taxes & fees

Oct 3 - Oct 4

A resort with multiple buildings, a central pool area, and surrounding greenery.

A spacious indoor area with a modern design, featuring a long corridor with seating and potted plants.

A lobby with artificial trees, a central spiral sculpture, and modern seating.

Lopesan Caoba Lagoon Resort Spa & Casino - All Inclusive

Bávaro

CA $418

CA $535 total

includes taxes & fees

Oct 27 - Oct 28

A resort with multiple swimming pools, a central fountain, and beachfront views.

A resort with a central swimming pool, lounge areas, and a view of the ocean.

A balcony with wicker furniture overlooking a beach with umbrellas and lounge chairs.

A spacious lobby with a high ceiling, a stone fireplace, a sofa set, and a round table.

Secrets Playa Esmeralda Resort & Spa - Adults Only - All Inclusive

Miches

CA $534

CA $534 total

includes taxes & fees

Sep 28 - Sep 29

A resort with a large infinity pool, palm trees, and a view of the water.

A restaurant with wooden furniture, large windows, and hanging lights.

A resort with multiple buildings, a large pool, and boats on the water.

A modern hotel room with a large bed, a TV, a balcony with a view of the sea, and a seating area.

Zemi Miches Punta Cana Resort, Curio by Hilton

Miches

CA $586

CA $750 total

includes taxes & fees

Oct 17 - Oct 18

A water park with multiple slides and a themed structure.

A modern building with large glass windows and a dining area with tables and chairs.

A bar area with a view of the beach and ocean, a bar counter, and a person preparing drinks.

A restaurant with a unique wall of terracotta pots, wicker furniture, and a cozy seating area.

Princess Family Club Bavaro - All Inclusive

Bávaro

CA $243

CA $311 total

includes taxes & fees

Oct 19 - Oct 20

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Caribbean Islands Hotel Reviews

Sunscape Coco Punta Cana - All Inclusive

Sunscape Coco Punta Cana - All Inclusive

10/10 Excellent

"Todo estuve excelente! Nos dieron un trato excepcional... y gracias a Carlos por siempre estar pendiente. Se los recomiendo!"

Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

10/10 Excellent

"From the time we arrived we were greeted with a warm welcome and a fruit punch rum drink. Our room was upgraded without having to ask. The staff for the entire trip was extremely helpful and always pleasant if any questions were asked. Food delicious! Entertainment checked off as you are never bored there. Such a amazing atmosphere we will definitely be back!"

San Juan Airport Hotel

San Juan Airport Hotel

10/10 Excellent

"Todo perfecto"

Ocean Blue & Sand Beach Resort - All Inclusive

Ocean Blue & Sand Beach Resort - All Inclusive

10/10 Excellent

"This place is wonderful, I stayed with my partner and the energy was great. The staff were kind and cool. The assistance from Gregorio from reception was exceptional. Leonel also make our stayed more fun and special. I will definitely go back, we loved it."

Majestic Elegance Punta Cana - All Inclusive

Majestic Elegance Punta Cana - All Inclusive

10/10 Excellent

"Nice"