Title: Book the Best Hotels with POOL in Lesser Antilles in 2025 | Expedia.ca

  

[Lesser Antilles Travel Guide](https://expedia.ca/Lesser-Antilles.dx3000655870)[Hotels in Lesser Antilles](https://expedia.ca/Lesser-Antilles-Hotels.d3000655870.Travel-Guide-Hotels)[Vacation Rentals in Lesser Antilles](https://expedia.ca/Lesser-Antilles-Vacation-Rentals.d3000655870.Travel-Guide-VacationRentals)[Flights to Lesser Antilles](https://expedia.ca/Cheap-Flights-To-Lesser-Antilles.d3000655870.Travel-Guide-Flights)[Lesser Antilles Car Rentals](https://expedia.ca/Car-Rentals-In-Lesser-Antilles.d3000655870.Car-Rental-Guide)[Lesser Antilles Vacation Packages](https://expedia.ca/Lesser-Antilles.d3000655870.Destination-Travel-Guides)

![Anguilla featuring rocky coastline, a beach and tropical scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/25000/25736-Anguilla.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find Hotels with a Pool in Lesser Antilles from CA $163

![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)

### 

Change your mind

Book hotels with free cancellation

![deals illustration](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)

![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)

### 

Be picky

Search almost a million properties worldwide

## Check availability on Lesser Antilles Hotels with a Pool

Tonight

[Sep 29 - Sep 30](https://www.expedia.ca/Hotel-Search?regionId=3000655870&startDate=2025-09-29&endDate=2025-09-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=3000655870&startDate=2025-09-30&endDate=2025-10-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=3000655870&startDate=2025-10-03&endDate=2025-10-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=3000655870&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Lesser Antilles Hotels with a Pool

![2 bars/lounges, swim-up bar, poolside bar, beach bar](https://images.trvl-media.com/lodging/1000000/170000/162200/162117/adea4f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges, swim-up bar, poolside bar, beach bar](https://images.trvl-media.com/lodging/1000000/170000/162200/162117/4dd07a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/1000000/170000/162200/162117/9b09ef78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, white sand, beach cabanas, beach towels](https://images.trvl-media.com/lodging/1000000/170000/162200/162117/435ff659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Westin St. Thomas Beach Resort & Spa

St. Thomas

8.2/10

Very good

(1037)

"Beautiful hotel..."

CA $370

CA $530 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/St-Thomas-Hotels-Marriott-Frenchmans-Reef-And-Morning-Star-Beach-Resort.h162117.Hotel-Information)

![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/651e7935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 restaurants, breakfast, lunch, dinner served; barbecue](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/9e796f89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 outdoor pools, open 7:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/5ecb34d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/cfa15203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Simpson Bay Resort, Marina & Spa

Pelican Key

9.0/10

Wonderful

(1365)

"Great place to stay with family. "

CA $144

CA $172 total

includes taxes & fees

Oct 22 - Oct 23

[](https://www.expedia.ca/Simpson-Bay-Hotels-Simpson-Bay-Resort.h1256868.Hotel-Information)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/800000/796500/796441/67b50717.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/800000/796500/796441/79cdb485.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sports facility](https://images.trvl-media.com/lodging/1000000/800000/796500/796441/7b01c7b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/800000/796500/796441/4b190380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key

9.0/10

Wonderful

(1254)

"Beautiful property would definitely stay here again "

CA $120

CA $163 total

includes taxes & fees

Sep 30 - Oct 1

[](https://www.expedia.ca/Simpson-Bay-Hotels-Flamingo-Beach-Resort-By-Diamond-Resorts.h796441.Hotel-Information)

![3 outdoor pools](https://images.trvl-media.com/lodging/10000000/9130000/9127100/9127018/263fd221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/10000000/9130000/9127100/9127018/5ea8bdad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/10000000/9130000/9127100/9127018/bd4eb8ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, white sand, scuba diving, snorkeling](https://images.trvl-media.com/lodging/10000000/9130000/9127100/9127018/5eecdd4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sugar Bay Resort and Spa

St. Thomas

7.2/10

Good

(293)

"its not full inclusive no vip room no café for expresso less everything no wet bar in room no room service we didn't have tissue in room I could keep going but the employees awesome the place awesome the bed awesome all inclusive NOT AWESOME"

[](https://www.expedia.ca/St-Thomas-Hotels-Sugar-Bay-Resort-And-Spa.h9127018.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/1000000/30000/23600/23522/5e7e9cb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/23600/23522/fca8b703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/23600/23522/c65799c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/1000000/30000/23600/23522/f5d68ae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jolly Beach Antigua - All-inclusive

Jolly Harbour

7.2/10

Good

(1014)

"The staff , dining options and the beach were all great. "

CA $218

CA $311 total

includes taxes & fees

Oct 1 - Oct 2

[](https://www.expedia.ca/Jolly-Harbour-Hotels-Jolly-Beach-Antigua-All-Inclusive.h23522.Hotel-Information)

![Grande Ocean view | View from room](https://images.trvl-media.com/lodging/1000000/530000/527200/527117/ee6de774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/530000/527200/527117/07241049.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 restaurants, breakfast, lunch, dinner served; seafood](https://images.trvl-media.com/lodging/1000000/530000/527200/527117/84639663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 restaurants, breakfast, lunch, dinner served; seafood](https://images.trvl-media.com/lodging/1000000/530000/527200/527117/59bd0d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Great Bay Beach Resort, Casino & Spa

Philipsburg

7.4/10

Good

(486)

"Food was great! A majority of the staff was great! Tried the rooms with Bali beds out front and that was a waste of money. No view and filled with ants. Get a higher room with an ocean view. The beach was useless as it is steep and ground seashells for sand. That said, you cannot beat the view of Simpson Bay. Great island and will be back when they rebuild. I would just stay at a sister property near the airport next time."

[](https://www.expedia.ca/Philipsburg-Hotels-Great-Bay-Beach-Resort.h527117.Hotel-Information)

![View from room](https://images.trvl-media.com/lodging/1000000/570000/565700/565666/1f9b225c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/570000/565700/565666/e0c3ab29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed with Sofa bed (1 Bedroom Ocean View Suite)](https://images.trvl-media.com/lodging/1000000/570000/565700/565666/d0493a66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/570000/565700/565666/w3840h2557x0y3-53955507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonesta Maho Beach All Inclusive Resort Casino & Spa

Lowlands

8.0/10

Very good

(2630)

"Great vacation highly recommend "

CA $258

CA $312 total

includes taxes & fees

Sep 30 - Oct 1

[](https://www.expedia.ca/Lowlands-Hotels-Sonesta-Maho-Beach-All-Inclusive-Resort-Casino-Spa.h565666.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/7e74429d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/3712236a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/937793bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 restaurants, breakfast, lunch, dinner served; Mexican cuisine](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/fd994a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Villas at Simpson Bay Resort

Simpson Bay

9.2/10

Wonderful

(1259)

"Great resort"

CA $177

CA $213 total

includes taxes & fees

Sep 30 - Oct 1

[](https://www.expedia.ca/Simpson-Bay-Hotels-The-Villas-At-Simpson-Bay-Beach-Resort-And-Marina.h4553784.Hotel-Information)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/190000/185300/185218/b4586a25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, beach umbrellas, snorkeling, beach bar](https://images.trvl-media.com/lodging/1000000/190000/185300/185218/4a925ac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/190000/185300/185218/e7272645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach views, serves lunch, dinner, and happy hour](https://images.trvl-media.com/lodging/1000000/190000/185300/185218/faad09d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Emerald Beach Resort

St. Thomas

7.6/10

Good

(1093)

"I love everything the workers are excellent, the hotel is beautiful, I recommend it."

CA $316

CA $388 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/St-Thomas-Hotels-Emerald-Beach-Resort.h185218.Hotel-Information)

![Surfing/boogie boarding](https://images.trvl-media.com/lodging/1000000/890000/886400/886307/ae480e2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Bedrooms, Oceanfront](https://images.trvl-media.com/lodging/1000000/890000/886400/886307/e9421eeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, espresso maker](https://images.trvl-media.com/lodging/1000000/890000/886400/886307/a65175ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Bedrooms, Oceanfront | Terrace/patio](https://images.trvl-media.com/lodging/1000000/890000/886400/886307/0f50474b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Grand Case Beach Club

Grand Case

9.4/10

Exceptional

(1016)

"The beach was amazing. The staff was really friendly. "

CA $292

CA $336 total

includes taxes & fees

Oct 1 - Oct 2

[](https://www.expedia.ca/Grand-Case-Hotels-Grand-Case-Beach-Club.h886307.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=2025-10-13&endDate=2025-10-14&regionId=3000655870&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true)

## Top Lesser Antilles Hotel Reviews

![Hilton Vacation Club Flamingo Beach St. Maarten](//images.trvl-media.com/lodging/1000000/800000/796500/796441/67b50717_y.jpg)

### Hilton Vacation Club Flamingo Beach St. Maarten

10/10 Excellent

"I loved everything - my room, the view, the beach"

[](https://expedia.ca/Simpson-Bay-Hotels-Flamingo-Beach-Resort-By-Diamond-Resorts.h796441.Hotel-Information)

![The Westin St. Thomas Beach Resort & Spa](//images.trvl-media.com/lodging/1000000/170000/162200/162117/adea4f9b_y.jpg)

### The Westin St. Thomas Beach Resort & Spa

10/10 Excellent

"Good and beautiful "

[](https://expedia.ca/St-Thomas-Hotels-Marriott-Frenchmans-Reef-And-Morning-Star-Beach-Resort.h162117.Hotel-Information)

![Sonesta Maho Beach All Inclusive Resort Casino & Spa](//images.trvl-media.com/lodging/1000000/570000/565700/565666/9a0f47b8_y.jpg)

### Sonesta Maho Beach All Inclusive Resort Casino & Spa

10/10 Excellent

"Everything was great! "

[](https://expedia.ca/Lowlands-Hotels-Sonesta-Maho-Beach-All-Inclusive-Resort-Casino-Spa.h565666.Hotel-Information)

![Cocobay Resort - All Inclusive - Adults Only](//images.trvl-media.com/lodging/1000000/900000/892100/892086/a378a9d4_y.jpg)

### Cocobay Resort - All Inclusive - Adults Only

10/10 Excellent

"Staff was amazing. Rooms are absolutely gorgeous 😍 food was great..."

[](https://expedia.ca/Valley-Church-Hotels-Cocobay-Resort-All-Inclusive-Adults-Only.h892086.Hotel-Information)

![Simpson Bay Resort, Marina & Spa](//images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg)

### Simpson Bay Resort, Marina & Spa

10/10 Excellent

"Wonderful stay. Clean. Walkable. "

[](https://expedia.ca/Simpson-Bay-Hotels-Simpson-Bay-Resort.h1256868.Hotel-Information)

![The Villas at Simpson Bay Resort](//images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/7e74429d_y.jpg)

### The Villas at Simpson Bay Resort

10/10 Excellent

"Amazing location. Friendly staff. Clean environment. Great restaurants. Spacious rooms. I highly recommend. I can’t wait not visit again "

[](https://expedia.ca/Simpson-Bay-Hotels-The-Villas-At-Simpson-Bay-Beach-Resort-And-Marina.h4553784.Hotel-Information)

![Margaritaville Vacation Club - St. Thomas](//images.trvl-media.com/lodging/12000000/11800000/11796200/11796106/29cf8be8_y.jpg)

### Margaritaville Vacation Club - St. Thomas

10/10 Excellent

"I enjoyed my stay and would stay here again."

[](https://expedia.ca/St-Thomas-Hotels-Margaritaville-Vacation-Club-By-Wyndham-St-Thomas.h11796106.Hotel-Information)

![Jolly Beach Antigua - All-inclusive](//images.trvl-media.com/lodging/1000000/30000/23600/23522/5e7e9cb3_y.jpg)

### Jolly Beach Antigua - All-inclusive

10/10 Excellent

"I did not like the absence of ice cream "

[](https://expedia.ca/Jolly-Harbour-Hotels-Jolly-Beach-Antigua-All-Inclusive.h23522.Hotel-Information)

![Lindbergh Bay Hotel and Villas](//images.trvl-media.com/lodging/7000000/6560000/6558700/6558668/767c40c4_y.jpg)

### Lindbergh Bay Hotel and Villas

10/10 Excellent

"Will definitely book again "

[](https://expedia.ca/St-Thomas-Hotels-Lindbergh-Bay-Hotel-And-Villas.h6558668.Hotel-Information)