Book the Best Hotels with POOL in Lesser Antilles in 2026

A beach with yellow lounge chairs, palm trees, a boat, and a pier.

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Our top choices for Lesser Antilles hotels with a pool

A swimming pool with clear blue water, a building with balconies, and palm trees.

A resort with multiple-story buildings, a well-maintained lawn, and a view of the ocean.

A pathway lined with palm trees and plants leading to a beach.

A beachfront hotel with a sandy beach, clear turquoise waters, and a rocky shoreline.

1. Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key

Splash into tropical bliss at this beachfront resort with a poolside bar and ocean panoramas.

CA $157

CA $202 total

includes taxes & fees

Oct 23 - Oct 24

A resort pool area with a view of the sea and sunset.

A restaurant with tables set for dining, large windows offering a view of the sunset over the ocean, and a ceiling fan.

A table set for two with a view of the sea and mountains at sunset.

An aerial view of a resort with multiple red-roofed buildings, a beach, and a clear blue sea.

2. Simpson Bay Resort, Marina & Spa

Pelican Key

Splash into aquatic bliss at this beachfront resort with six sun-drenched pools.

CA $205

CA $249 total

includes taxes & fees

Oct 6 - Oct 7

A balcony with a view of a beach and pool area, including lounge chairs and umbrellas.

A beachfront hotel with a pool area, palm trees, and ocean views.

A balcony with a view of the ocean and a beach.

3. Royal Islander Resort La Plage

Lowlands

Immerse in poolside paradise with 24-hour swim access and beachfront luxury at this resort.

CA $188

CA $230 total

includes taxes & fees

Oct 6 - Oct 7

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

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

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

A balcony with a metal chair, a green fence, and a view of the ocean 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 $134

CA $155 total

includes taxes & fees

Nov 3 - Nov 4

A pool area with a rectangular pool, surrounded by hexagonal tiles, and furnished with white chairs and tables.

A balcony with a view of a hillside town, a table with chairs, and a potted plant.

A balcony with a view of greenery, a table with chairs, and a potted plant.

A covered outdoor area with a terrace, white metal chairs, a table, and a view of buildings and greenery.

5. Bunker Hill Hotel

St. Thomas

Dreamy pool paradise with mesmerizing city views makes this island oasis unforgettable.

CA $113

CA $140 total

includes taxes & fees

Oct 28 - Oct 29

A hotel interior with a balcony, outdoor seating, and a pool area.

A hallway with a marble floor, a wooden door, and a metal handrail.

A kitchen area with a coffee station featuring a coffee maker and multiple cups and saucers.

A spacious living room with a fireplace, a dining area with wooden chairs, and a staircase leading to an upper level.

6. Vieques BioBay Bed and Breakfast

Vieques

CA $276

CA $611 total

includes taxes & fees

Nov 2 - Nov 3

A swimming pool with tiled edges, surrounded by tropical vegetation and a building labeled "Departure Lounge".

A balcony with wicker chairs and a table overlooking a beach with lounge chairs and palm trees.

A beach view with palm trees, a sandy area, and a clear blue sky.

A beachfront hotel with a sandy beach, palm trees, and a pool area.

7. Mary's Boon Beach Resort & Spa

Simpson Bay

Dive into tropical relaxation at this hotel's poolside oasis, where beach meets bliss.

CA $178

CA $213 total

includes taxes & fees

Oct 13 - Oct 14

A swimming pool with clear water, surrounded by lounge chairs and a wooden deck.

An outdoor seating area with white wicker furniture and a view of the beach and ocean.

A hotel room with a large bed, a desk, and a ceiling fan.

A bedroom with two beds, a bathroom, and a view of the beach.

8. Wyndham Tortola BVI Lambert Beach Resort

East End

Plunge into paradise with this beachside oasis, where crystal waters meet pristine shorelines.

CA $292

CA $350 total

includes taxes & fees

Oct 27 - Oct 28

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Choose what matters most at hotels with a pool in Lesser Antilles

Breakfast included

4 stars

5 stars

Hot tub

Spa

Hotels with pools and free breakfast in Lesser Antilles

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key

CA $157

CA $202 total

includes taxes & fees

Oct 23 - Oct 24

A beach with thatched umbrellas and lounge chairs, a palm tree, and a building in the background.

Simpson Bay Resort, Marina & Spa

Pelican Key

CA $205

CA $249 total

includes taxes & fees

Oct 6 - Oct 7

A balcony with a pool, chairs, and potted plants.

A hotel room with two beds, a nightstand, a lamp, and an air conditioning unit.

A balcony with a tiled floor and a metal railing, overlooking a residential area with red-roofed houses and greenery.

Bunker Hill Hotel

St. Thomas

CA $113

CA $140 total

includes taxes & fees

Oct 28 - Oct 29

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

A lobby with a central seating area, a reception desk, and a sign reading "KARMER'S MARKET".

A spacious lobby with a view of the ocean, featuring comfortable seating and a ceiling with a unique light design.

A well-maintained garden with palm trees, a pathway, and a view of the ocean.

Blue Horizon Boutique Resort - Adults Only

Esperanza

CA $224

CA $256 total

includes taxes & fees

Oct 6 - Oct 7

A wooden deck with white wicker furniture and a view of the ocean.

Wyndham Tortola BVI Lambert Beach Resort

East End

CA $292

CA $350 total

includes taxes & fees

Oct 27 - Oct 28

A beach with clear turquoise water, sandy shore, and lounge chairs with blue umbrellas.

A tropical garden with palm trees and a white building with a window.

A table with three drinks and a glass of water on a wooden deck overlooking the beach.

An aerial view of a beach resort with a swimming pool, numerous blue umbrellas, and a clear turquoise sea.

Sand Castle on the Beach - Adults Only

Frederiksted

CA $308

CA $347 total

includes taxes & fees

Oct 4 - Oct 5

A beachside restaurant with outdoor seating, a view of the ocean, and a thatched roof.

A resort with a beach, a swimming pool, and lush greenery.

A spacious outdoor dining area with wicker furniture and a pool view.

A beach with palm trees and a clear blue sky.

The Buccaneer Beach & Golf Resort

Christiansted

CA $345

CA $445 total

includes taxes & fees

Oct 9 - Oct 10

A balcony with a pool, clear turquoise water, and a distant ship.

A coastal scene with clear turquoise waters, a rocky shoreline, and dense foliage.

A deck with two lounge chairs and a railing overlooking turquoise ocean waters.

A wooden pathway flanked by lush greenery and tropical plants, leading to a white building.

Sapphire Beach Club Resort

Maho

CA $133

CA $163 total

includes taxes & fees

Nov 3 - Nov 4

A beach with clear turquoise water, a sandy shore, and a hotel with multiple balconies overlooking the sea.

A poolside bar with wooden chairs and a tiled floor, overlooking a swimming pool.

A balcony with a view of a pool and beach, a table with a vase of flowers, and a chair.

A wooden table with chairs on a balcony overlooking a beach and ocean.

Royal Islander Resort La Terrasse

Lowlands

CA $161

CA $198 total

includes taxes & fees

Oct 5 - Oct 6

A beach with rows of blue and white sun loungers under large blue umbrellas, a hotel building in the background, and a clear blue sky.

A hotel room with a large bed, a bench, a TV, and a view of the city through the sliding doors.

A modern bedroom with a large bed, a wooden ceiling, and a painting on the wall.

A spa interior with a reception desk, a blue chair, and a wall with a sign reading "Aquarius Spa".

The Atrium Beach Resort and Spa, an Ascend Collection Resort

Simpson Bay

CA $227

CA $289 total

includes taxes & fees

Oct 22 - Oct 23

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4-star hotels with pools in Lesser Antilles

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key

CA $157

CA $202 total

includes taxes & fees

Oct 23 - Oct 24

A pathway leading to a beach area with palm trees and a view of the ocean.

A spacious lobby with a curved blue sofa, a modern chandelier, and a view of the kitchen and dining area.

Royal Islander Resort La Plage

Lowlands

CA $188

CA $230 total

includes taxes & fees

Oct 6 - Oct 7

The Buccaneer Beach & Golf Resort

Christiansted

CA $345

CA $445 total

includes taxes & fees

Oct 9 - Oct 10

Wyndham Tortola BVI Lambert Beach Resort

East End

CA $292

CA $350 total

includes taxes & fees

Oct 27 - Oct 28

A resort with multiple hotel buildings, a marina, and a clear blue ocean.

A buffet setup with various food items and a view of the marina through large windows.

A coastal hotel with a marina, clear turquoise water, and a backdrop of lush mountains.

A coastal hotel with multiple buildings, a dock, and clear turquoise waters.

The Villas at Simpson Bay Resort

Pelican Key

CA $235

CA $286 total

includes taxes & fees

Oct 5 - Oct 6

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

A coastal hotel with multiple red-roofed buildings, a beach, and a cruise ship in the background.

A hotel lobby with multiple seating areas, a central bar, and a kitchen visible in the background.

A rooftop bar with outdoor seating, overlooking a coastal area.

Divi Little Bay Beach Resort

Philipsburg

CA $241

CA $313 total

includes taxes & fees

Oct 14 - Oct 15

A beachfront resort with multiple lounge areas and a pool.

An outdoor bar area with wooden tables and chairs, red umbrellas, and a view of the sea.

A table with plates of food and drinks, overlooking a beach with clear turquoise water.

An aerial view of a beach resort with a large house, multiple lounge chairs, and umbrellas.

Siboney Beach Club

St. John's

CA $265

CA $350 total

includes taxes & fees

Oct 4 - Oct 5

A clear blue pool with lounge chairs and palm trees, overlooking the ocean.

A modern hotel lobby with a black limousine, a polished floor, and a blue and wooden ceiling.

A hotel room with a large bed, a TV, and a view of the ocean.

A modern hotel with a glass infinity pool overlooking the ocean, lounge chairs, and a clear view of the sea.

The Morgan Resort Spa Village

Simpson Bay

CA $531

CA $671 total

includes taxes & fees

Oct 5 - Oct 6

A resort pool area with a curved design, lounge chairs, umbrellas, and a building with a light-colored facade.

A dining table set for six with a bottle of wine, surrounded by wicker chairs, overlooking a body of water and a mountainous landscape.

A coastal hotel with multiple buildings, a dock, and a mountainous backdrop.

A beach with clear turquoise water, a sandy shore, and white buildings on a hillside.

Oyster Bay Beach Resort

Oyster Pond

CA $234

CA $281 total

includes taxes & fees

Oct 13 - Oct 14

Royal Islander Resort La Terrasse

Lowlands

CA $161

CA $198 total

includes taxes & fees

Oct 5 - Oct 6

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5-star hotels with pools in Lesser Antilles

A pool area with lounge chairs and umbrellas, surrounded by palm trees, and a view of the sea.

A beachside resort with striped blue and white umbrellas, lounge chairs, and a clear view of the ocean.

A coastal resort with a beachfront, multiple hotel buildings, and a swimming pool area.

A coastal town with red-roofed buildings, a marina with boats, and lush greenery.

JW Marriott St. Maarten Beach Resort & Spa

Oyster Pond

CA $442

CA $579 total

includes taxes & fees

Oct 9 - Oct 10

A resort with a large pool area, multiple levels of water features, and numerous sun loungers with umbrellas.

A spacious living room with a large sliding glass door leading to a balcony with a view of the sea and a mountain. There is a sofa, a coffee table, and a lamp.

A resort with a pool, beach, and lush greenery.

A bar area with a long counter, multiple bar stools, and large windows offering a view of the sea and mountains.

Scrub Island Resort, Spa & Marina

Scrub Island

CA $656

CA $872 total

includes taxes & fees

Nov 2 - Nov 3

A pathway leading to a pool with palm trees and umbrellas, overlooking a body of water.

A beach with clear turquoise waters, a sandy shore, and a distant mountain range.

A modern outdoor seating area with a view of the ocean, white furniture, and a chandelier.

A spacious living area with a large sofa set, a dining area with bar stools, and a kitchen with white cabinets and pendant lighting.

Four Seasons Resort - Nevis

Jessups Village

CA $841

CA $1,090 total

includes taxes & fees

Oct 12 - Oct 13

A modern hotel with a pool on a rocky outcrop, overlooking the sea.

A waiter pouring champagne into a glass at a table with a bottle of champagne, a glass of champagne, and a basket of strawberries.

A modern room with a long black countertop, large windows with a view of the ocean, and a curtain.

A beach scene with clear turquoise water and a rocky shoreline.

Sonesta Ocean Point All Inclusive, Adults Only Resort

Lowlands

CA $969

CA $1,173 total

includes taxes & fees

Oct 13 - Oct 14

A resort with a large infinity pool, a central building with a peaked roof, and a stone tower.

A wooden deck with a white bathtub, a small table, and a view of the ocean.

A bedroom with a large bed, a desk with books and a lamp, and a view of the ocean through an open door.

An outdoor pool area with lounge chairs, a bar, and a covered seating area with a view of the pool.

Belle Mont Sanctuary Resort

Saint Pauls

CA $498

CA $607 total

includes taxes & fees

Oct 24 - Oct 25

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

A spacious living room with a large window overlooking a beach, furnished with a sofa, chairs, and a coffee table.

A resort with multiple buildings, a swimming pool, and a beach area with sun loungers and umbrellas.

A wooden staircase leading to a traditional building surrounded by trees.

Zemi Beach House, LXR Hotels & Resorts

Shoal Bay

CA $742

CA $942 total

includes taxes & fees

Nov 2 - Nov 3

A poolside area with lounge chairs and umbrellas, a person in a white robe, and a view of the sea and hills in the background.

A room with a view of the ocean, a wooden ceiling, and a seating area with a round table.

A wooden deck with a view of the sea and mountains, a stone planter, and a table with a towel and a box.

A room with two beds, a view of the sea, and a small pool.

Christopher Hotel

Pointe Milou

CA $1,236

CA $1,559 total

includes taxes & fees

Oct 24 - Oct 25

An aerial view of a resort with multiple swimming pools, a beach, and a boat docked near the shore.

A resort with multiple buildings, a beach, and clear turquoise waters.

A room with two beds, a view of the ocean, and a balcony with white railings.

A spacious lobby with high ceilings, arched columns, and hanging chandeliers.

The Ritz-Carlton, St. Thomas

St. Thomas

CA $782

CA $1,074 total

includes taxes & fees

Oct 4 - Oct 5

A resort with multiple swimming pools, water slides, and sun loungers.

A resort with white buildings, palm trees, and a view of the ocean.

A covered outdoor seating area with wooden tables and chairs, overlooking a beach with clear turquoise water and white sand.

A hotel room with a large window offering a view of the ocean and mountains. There is a bed, a green armchair, a sofa, and a desk with a chair.

Aurora Anguilla Resort & Golf Club

Rendezvous Bay

CA $852

CA $1,065 total

includes taxes & fees

Nov 2 - Nov 3

A modern pool area with clear blue water, a glass barrier, and a view of the ocean and distant hills.

A corridor with glass display cabinets and a view of a beach.

A wooden deck with outdoor seating, a view of the ocean, and a mountain in the background.

An aerial view of a resort with multiple swimming pools, beachfront, and lush greenery.

Park Hyatt St. Kitts

Basseterre

CA $925

CA $1,246 total

includes taxes & fees

Oct 24 - Oct 25

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 Lesser Antilles Hotel Reviews

Margaritaville Vacation Club - St. Thomas

8/10 Good

"Friendly, helpful staff overall. Neil, the shuttle driver was great. Show him some love if you visit."

Oyster Bay Beach Resort

8/10 Good

"I had a nice time however I never was approached by anyone to order anything ie,drink,food,etc while at the pool area. The resort did this years previous but not this time."

Cocobay Resort Antigua - All Inclusive - Adults Only

10/10 Excellent

"My wife and I went in the end of September. I could not recommend Cocobay Resort more highly. Everything was perfect, the"

Sonesta Ocean Point All Inclusive, Adults Only Resort

8/10 Good

"Hotel was clean, staff during the day were very helpful, but the staff during the evening seemed bothered when they were asked where to rent a car, of if they knew the prices."

Emerald Beach Resort

10/10 Excellent

"A1"

Jolly Beach Antigua - All-inclusive

8/10 Good

"Overall experience was good for the cost."

The Morgan Resort Spa Village

10/10 Excellent

"Beautiful hotel, great staff, and perfect location."

Bunker Hill Hotel

10/10 Excellent

"Excelente lugar para hospedaje"

Divi Little Bay Beach Resort

10/10 Excellent

"Last year we stayed at Little Debbland we had an ocean view"

Find Hotels with a Pool in Lesser Antilles from CA $140

Change your mind

Treat yourself

Be picky

Check availability on Lesser Antilles Hotels with a Pool

Our top choices for Lesser Antilles hotels with a pool

1. Hilton Vacation Club Flamingo Beach St. Maarten

2. Simpson Bay Resort, Marina & Spa

3. Royal Islander Resort La Plage

4. Sea Gate Hotel

5. Bunker Hill Hotel

6. Vieques BioBay Bed and Breakfast

7. Mary's Boon Beach Resort & Spa

8. Wyndham Tortola BVI Lambert Beach Resort

9. La Vue Boutique Inn

10. Sand Castle on the Beach - Adults Only

Choose what matters most at hotels with a pool in Lesser Antilles

Hotels with pools and free breakfast in Lesser Antilles

Hilton Vacation Club Flamingo Beach St. Maarten

Simpson Bay Resort, Marina & Spa

Bunker Hill Hotel

Blue Horizon Boutique Resort - Adults Only

Wyndham Tortola BVI Lambert Beach Resort

Sand Castle on the Beach - Adults Only

The Buccaneer Beach & Golf Resort

Sapphire Beach Club Resort

Royal Islander Resort La Terrasse

The Atrium Beach Resort and Spa, an Ascend Collection Resort

4-star hotels with pools in Lesser Antilles

Hilton Vacation Club Flamingo Beach St. Maarten

Royal Islander Resort La Plage

The Buccaneer Beach & Golf Resort

Wyndham Tortola BVI Lambert Beach Resort

The Villas at Simpson Bay Resort

Divi Little Bay Beach Resort

Siboney Beach Club

The Morgan Resort Spa Village

Oyster Bay Beach Resort

Royal Islander Resort La Terrasse

5-star hotels with pools in Lesser Antilles

JW Marriott St. Maarten Beach Resort & Spa

Scrub Island Resort, Spa & Marina

Four Seasons Resort - Nevis

Sonesta Ocean Point All Inclusive, Adults Only Resort

Belle Mont Sanctuary Resort

Zemi Beach House, LXR Hotels & Resorts

Christopher Hotel

The Ritz-Carlton, St. Thomas

Aurora Anguilla Resort & Golf Club

Park Hyatt St. Kitts

Top Lesser Antilles Hotel Reviews

Margaritaville Vacation Club - St. Thomas

Oyster Bay Beach Resort

Cocobay Resort Antigua - All Inclusive - Adults Only

Sonesta Ocean Point All Inclusive, Adults Only Resort

Emerald Beach Resort

Jolly Beach Antigua - All-inclusive

The Morgan Resort Spa Village

Bunker Hill Hotel

Divi Little Bay Beach Resort