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

[Caribbean Islands Travel Guide](https://expedia.ca/Caribbean-Islands.dx3000652683)[Hotels in Caribbean Islands](https://expedia.ca/Caribbean-Islands-Hotels.d3000652683.Travel-Guide-Hotels)[Vacation Rentals in Caribbean Islands](https://expedia.ca/Caribbean-Islands-Vacation-Rentals.d3000652683.Travel-Guide-VacationRentals)[Flights to Caribbean Islands](https://expedia.ca/Cheap-Flights-To-Caribbean-Islands.d3000652683.Travel-Guide-Flights)[Caribbean Islands Car Rentals](https://expedia.ca/Car-Rentals-In-Caribbean-Islands.d3000652683.Car-Rental-Guide)[Caribbean Islands Vacation Packages](https://expedia.ca/Caribbean-Islands.d3000652683.Destination-Travel-Guides)

![Panoramic view of a tropical beach paradise with a calm sea and palm trees.](https://images.trvl-media.com/place/3000652683/0f906013-1c42-421c-97bc-ef4a41f0db0e.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find Hotels with a Pool in Caribbean Islands from CA $102

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)  
###  
Change your mind  
Book hotels with free cancellation
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)  
###  
Treat yourself  
Sign in to save 10% or more on thousands of hotels  
[Sign in](https://www.expedia.ca/login)
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)  
###  
Be picky  
Search almost a million properties worldwide

## Check availability on Caribbean Islands Hotels with a Pool

Tonight

[Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-12-10&endDate=2025-12-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-12-11&endDate=2025-12-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Caribbean Islands hotels with a pool

![Outdoor pool](https://images.trvl-media.com/lodging/110000000/109850000/109847300/109847255/w3837h2557x3y4-c676216b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/110000000/109850000/109847300/109847255/w3836h2557x4y4-5dc9718e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109850000/109847300/109847255/23d2b62b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/110000000/109850000/109847300/109847255/w3836h2558x4y3-694aa831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Santiago, Curio Collection by Hilton

[](https://www.expedia.ca/Santiago-De-Los-Caballeros-Hotels-Hotel-Santiago.h109847255.Hotel-Information)

Villa Olga

9.6/10

Exceptional

(337)

"Very well located it , beautiful rooms and amazing staff👍👍"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Luis

CA $176

CA $225 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Santiago-De-Los-Caballeros-Hotels-Hotel-Santiago.h109847255.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/5000000/4680000/4675500/4675477/d9e16d0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Horseback riding](https://images.trvl-media.com/lodging/5000000/4680000/4675500/4675477/438a5d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4680000/4675500/4675477/9f09ebef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/5000000/4680000/4675500/4675477/cb0df333.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sea Gate Hotel

[](https://www.expedia.ca/Vieques-Hotels-Sea-Gate-Hotel.h4675477.Hotel-Information)

Isabel II

9.4/10

Exceptional

(1001)

"Wonderful staff, perfect location. Best beds on our entire vacation. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dock

CA $166

CA $190 total

includes taxes & fees

Jan 3 - Jan 4, 2026

[](https://www.expedia.ca/Vieques-Hotels-Sea-Gate-Hotel.h4675477.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/1000000/450000/443100/443089/1caf2548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/450000/443100/443089/03b4144f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/450000/443100/443089/25a7a14c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hotel Room | View from room](https://images.trvl-media.com/lodging/1000000/450000/443100/443089/127fd01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Siesta Hotel

[](https://www.expedia.ca/St-Georges-Hotels-Siesta-Hotel.h443089.Hotel-Information)

St. George's

9.0/10

Wonderful

(1003)

"Great peaceful hotel in a wonderful location in Grand Anse"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Farrah

CA $101

CA $121 total

includes taxes & fees

Dec 11 - Dec 12

[](https://www.expedia.ca/St-Georges-Hotels-Siesta-Hotel.h443089.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/96000000/95510000/95505700/95505606/115417e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sundeck](https://images.trvl-media.com/lodging/96000000/95510000/95505700/95505606/225d72dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/96000000/95510000/95505700/95505606/2d1522eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/96000000/95510000/95505700/95505606/617c653a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Pinar Dorado by Gran Jimenoa

[](https://www.expedia.ca/Santiago-De-Los-Caballeros-Hotels-Hotel-Pinar-Dorado-By-Gran-Jimenoa.h95505606.Hotel-Information)

Jarabacoa

9.4/10

Exceptional

(222)

"The installations have been renovated and the hotel is very beautiful with a modern feel. The staff is very attentive and polite. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Luis

CA $126

CA $162 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Santiago-De-Los-Caballeros-Hotels-Hotel-Pinar-Dorado-By-Gran-Jimenoa.h95505606.Hotel-Information)

![Exercise/lap pool](https://images.trvl-media.com/lodging/1000000/910000/902000/901912/cd278f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/910000/902000/901912/e0c1ed04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/1000000/910000/902000/901912/e2a87c90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fountain](https://images.trvl-media.com/lodging/1000000/910000/902000/901912/e59473f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Vacation Club at Hacienda del Mar, Dorado

[](https://www.expedia.ca/Vega-Alta-Hotels-Hyatt-Vacation-Club-At-Hacienda-Del-Mar.h901912.Hotel-Information)

Sabana

9.4/10

Exceptional

(2955)

"Such a great and relaxing stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Diana

CA $279

CA $364 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Vega-Alta-Hotels-Hyatt-Vacation-Club-At-Hacienda-Del-Mar.h901912.Hotel-Information)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/74000000/73570000/73568300/73568283/eefa56ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/74000000/73570000/73568300/73568283/26987c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/74000000/73570000/73568300/73568283/511cbfc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/74000000/73570000/73568300/73568283/332dc5ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Royal Delonix Hotel

[](https://www.expedia.ca/Penuelas-Hotels-Royal-Delonix-Hotel.h73568283.Hotel-Information)

Penuelas

9.2/10

Wonderful

(314)

"Small hotel, great staff, clean rooms, great restaurant. Would return. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Emmanuel

CA $93

CA $102 total

includes taxes & fees

Dec 23 - Dec 24

[](https://www.expedia.ca/Penuelas-Hotels-Royal-Delonix-Hotel.h73568283.Hotel-Information)

![Outdoor pool, open 10:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/13000000/12950000/12948900/12948837/1b5a351b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Food and drink](https://images.trvl-media.com/lodging/13000000/12950000/12948900/12948837/3401aa00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/13000000/12950000/12948900/12948837/8aeece03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach/ocean view](https://images.trvl-media.com/lodging/13000000/12950000/12948900/12948837/ddbc1d4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Catalonia Santo Domingo

[](https://www.expedia.ca/Santo-Domingo-Hotels-Catalonia-Santo-Domingo.h12948837.Hotel-Information)

Ciudad Universitaria

8.8/10

Excellent

(1729)

"Everything was great, very clean, good food, excelent amenities."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

FELIX

CA $144

CA $184 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Santo-Domingo-Hotels-Catalonia-Santo-Domingo.h12948837.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/36000000/35380000/35372900/35372844/104b2d48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; international cuisine, beach views ](https://images.trvl-media.com/lodging/36000000/35380000/35372900/35372844/0ae1ddbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; international cuisine, beach views ](https://images.trvl-media.com/lodging/36000000/35380000/35372900/35372844/e55f1e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/36000000/35380000/35372900/35372844/70b25a59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hommage Hotel & Residences

[](https://www.expedia.ca/Nettle-Bay-Hotels-Hommage-Hotel-Residences.h35372844.Hotel-Information)

Nettle Bay

8.4/10

Very good

(513)

"Had a spacious room at Hommage, and it was convenient to have the restaurant on site. Restaurant was a bit pricey for the quality of food. the pool was great, right on the lagoon and large. service at front desk was friendly "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Randall

CA $221

CA $230 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Nettle-Bay-Hotels-Hommage-Hotel-Residences.h35372844.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/100000000/99780000/99777200/99777103/4cb9df11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premier Suite](https://images.trvl-media.com/lodging/100000000/99780000/99777200/99777103/w3836h2556x4y4-99726840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/100000000/99780000/99777200/99777103/8747d4c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/100000000/99780000/99777200/99777103/w3837h2557x3y3-fc67853c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Centric Santo Domingo

[](https://www.expedia.ca/Santo-Domingo-Hotels-Hyatt-Centric-Santo-Domingo.h99777103.Hotel-Information)

Piantini

9.6/10

Exceptional

(161)

"Great service. We had a great experience at the restaurant there. Nataly and Agripina were attentive, kind, and always made sure we were taken care of. Highly recommend. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

BELKYS

CA $165

CA $211 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Santo-Domingo-Hotels-Hyatt-Centric-Santo-Domingo.h99777103.Hotel-Information)

![2 outdoor pools](https://images.trvl-media.com/lodging/9000000/8740000/8730600/8730567/0ab77931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/9000000/8740000/8730600/8730567/53bc89e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/9000000/8740000/8730600/8730567/b619af9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/9000000/8740000/8730600/8730567/e4d188bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Boho Beach Club

[](https://www.expedia.ca/Cabo-Rojo-Hotels-Boho-Beach-Club.h8730567.Hotel-Information)

Cabo Rojo

9.0/10

Wonderful

(755)

"It was a really nice property. I enjoy my stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Xavier

CA $128

CA $156 total

includes taxes & fees

Dec 13 - Dec 14

[](https://www.expedia.ca/Cabo-Rojo-Hotels-Boho-Beach-Club.h8730567.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-24&endDate=2025-12-25&regionId=3000652683&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true)

## Top Caribbean Islands Hotel Reviews

![Holiday Inn Resort Aruba - Beach Resort & Casino by IHG](https://images.trvl-media.com/lodging/1000000/10000/6000/5956/6f50ef2e_y.jpg)

### Holiday Inn Resort Aruba - Beach Resort & Casino by IHG

10/10 Excellent

"The room was very clean and anything needed during our stay was easily within walking distance. The staff, especially the housekeeping staff was exceptional. They were very friendly and attentive to our needs. Will definitely return to Holiday Inn on our stays in the future."

[](https://expedia.ca/Noord-Hotels-Holiday-Inn-Resort-Aruba-Beach-Resort-And-Casino.h5956.Hotel-Information)

![Hyatt Vacation Club at Hacienda del Mar, Dorado](https://images.trvl-media.com/lodging/1000000/910000/902000/901912/cd278f86_y.jpg)

### Hyatt Vacation Club at Hacienda del Mar, Dorado

10/10 Excellent

"Great view, clean rooms and quality restaurant/bar on premises."

[](https://expedia.ca/Vega-Alta-Hotels-Hyatt-Vacation-Club-At-Hacienda-Del-Mar.h901912.Hotel-Information)

![Majestic Elegance Punta Cana - All Inclusive](https://images.trvl-media.com/lodging/3000000/2200000/2191900/2191836/fe18cfe4_y.jpg)

### Majestic Elegance Punta Cana - All Inclusive

10/10 Excellent

"Amazing "

[](https://expedia.ca/Punta-Cana-Hotels-Majestic-Elegance-Punta-Cana-All-Inclusive.h2191836.Hotel-Information)

![Hotel Riu Palace Antillas - Adults Only - All Inclusive](https://images.trvl-media.com/lodging/1000000/30000/28700/28648/c1474878_y.jpg)

### Hotel Riu Palace Antillas - Adults Only - All Inclusive

10/10 Excellent

"0825, November 28-Dec 4th."

[](https://expedia.ca/Noord-Hotels-Riu-Palace-Antillas-All-Inclusive-Adult-Only.h28648.Hotel-Information)

![Barceló Bávaro Palace - All Inclusive](https://images.trvl-media.com/lodging/3000000/2440000/2438600/2438582/b9a77204_y.jpg)

### Barceló Bávaro Palace - All Inclusive

10/10 Excellent

"Everything Good!!"

[](https://expedia.ca/Punta-Cana-Hotels-Barcelo-Bavaro-Palace-All-Inclusive.h2438582.Hotel-Information)

![Renaissance Wind Creek Aruba Resort](https://images.trvl-media.com/lodging/1000000/30000/28400/28399/816cc91c_y.jpg)

### Renaissance Wind Creek Aruba Resort

10/10 Excellent

"Amazing service. The best hotel I’ve ever stayed in!"

[](https://expedia.ca/Oranjestad-Hotels-Renaissance-Aruba-Resort-Casino.h28399.Hotel-Information)

![Hotel Riu Republica - Adults only - All Inclusive](https://images.trvl-media.com/lodging/13000000/12850000/12848900/12848883/1639414b_y.jpg)

### Hotel Riu Republica - Adults only - All Inclusive

10/10 Excellent

"Gracias deberían de tener en cuenta pal de cosas como el olor en el elevador el agua caliente y el otro elevado no sirve pero de lo demás 10/10 gracias"

[](https://expedia.ca/Punta-Cana-Hotels-Riu-Republica-Adults-Only-All-Inclusive.h12848883.Hotel-Information)

![Excellence El Carmen - Adults Only All Inclusive](https://images.trvl-media.com/lodging/13000000/12580000/12570800/12570728/f82745ac_y.jpg)

### Excellence El Carmen - Adults Only All Inclusive

10/10 Excellent

"The resort is good. The staff is amazing especially Dariel who does all the entertainment and the poolside bartender Rocsil (not sure if that was the correct spelling) was attentive and phenomenal."

[](https://expedia.ca/Punta-Cana-Hotels-Excellence-El-Carmen-Adults-Only-All-Inclusive.h12570728.Hotel-Information)

![La Concha Resort, Puerto Rico, Autograph Collection](https://images.trvl-media.com/lodging/2000000/1770000/1760300/1760259/22470d47_y.jpg)

### La Concha Resort, Puerto Rico, Autograph Collection

10/10 Excellent

"My stay here was incredible. The staff was welcoming, tended to our needs. I luved my room and the view but i think what i paid for wasn't reasonable. Over all 10 out of 10."

[](https://expedia.ca/San-Juan-Hotels-La-Concha-Renaissance-San-Juan-Resort.h1760259.Hotel-Information)