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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Check availability on Lesser Antilles Hotels with a Pool

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Our top choices for Lesser Antilles hotels with a pool

Vieques BioBay Bed and Breakfast

Vieques

CA $569 total

includes taxes & fees

Jul 10 - Jul 11

Sea Gate Hotel

Isabel II

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

CA $171 total

includes taxes & fees

Jul 11 - Jul 12

Nanny Cay Resort and Marina

Road Town

Tropical oasis offers poolside dining, beach activities, outdoor pool, and children's splash zone.

CA $345 total

includes taxes & fees

Jul 16 - Jul 17

The Moorings Yacht Club Hotel

Road Town

CA $333 total

includes taxes & fees

Aug 2 - Aug 3

Club Vieques - Adults Only Resort - LGBT Friendly

Vieques

Dive into tropical bliss at this adults-only resort with a sun-soaked pool area surrounded by lush island scenery.

CA $288 total

includes taxes & fees

Jul 22 - Jul 23

Outdoor pool, pool umbrellas, sun loungers

Old Crow Hotel and Suites

Vieques

Turquoise waters meet island serenity at this serene pool oasis with Caribbean views.

CA $235 total

includes taxes & fees

Jul 6 - Jul 7

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 $216 total

includes taxes & fees

Jul 19 - Jul 20

The Cove Hotel St.Croix

Christiansted

Dive into tropical relaxation at this St. Croix hotel's sun-drenched outdoor pool, just moments from pristine Cane Bay Beach.

CA $223 total

includes taxes & fees

Jul 7 - Jul 8

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

Breakfast included

4 stars

Hotels with pools and free breakfast in Lesser Antilles

Vieques BioBay Bed and Breakfast

Vieques

CA $569 total

includes taxes & fees

Jul 10 - Jul 11

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key

CA $216 total

includes taxes & fees

Jul 19 - Jul 20

The Buccaneer Beach & Golf Resort

Christiansted

CA $524 total

includes taxes & fees

Jul 25 - Jul 26

Wyndham Tortola BVI Lambert Beach Resort

East End

CA $314 total

includes taxes & fees

Jul 6 - Jul 7

Blue Horizon Boutique Resort - Adults Only

Esperanza

CA $410 total

includes taxes & fees

Jul 16 - Jul 17

Koi Resort Saint Kitts, Curio Collection by Hilton

Basseterre

CA $254 total

includes taxes & fees

Jul 17 - Jul 18

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4-star hotels with pools in Lesser Antilles

The Buccaneer Beach & Golf Resort

Christiansted

CA $524 total

includes taxes & fees

Jul 25 - Jul 26

Keyonna Beach - All Inclusive - Couples Only

Johnson's Point

CA $1,121 total

includes taxes & fees

Jul 9 - Jul 10

Wyndham Tortola BVI Lambert Beach Resort

East End

CA $314 total

includes taxes & fees

Jul 6 - Jul 7

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Lowlands

CA $810 total

includes taxes & fees

Aug 3 - Aug 4

Royalton Antigua, An Autograph Collection All-Inclusive Resort

Five Islands Village

CA $778 total

includes taxes & fees

Jul 7 - Jul 8

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5-star hotels with pools in Lesser Antilles

3 outdoor pools, pool umbrellas, sun loungers

Scrub Island Resort, Spa & Marina

Scrub Island

CA $819 total

includes taxes & fees

Jul 8 - Jul 9

Outdoor pool, cabanas (surcharge), pool umbrellas

JW Marriott St. Maarten Beach Resort & Spa

Oyster Pond

CA $570 total

includes taxes & fees

Jul 22 - Jul 23

3 restaurants; breakfast, lunch, and dinner served

Sonesta Ocean Point All Inclusive, Adults Only Resort

Lowlands

CA $1,028 total

includes taxes & fees

Jul 20 - Jul 21

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Top Lesser Antilles Hotel Reviews

Simpson Bay Resort, Marina & Spa

10/10 Excellent

"We had a wonderful stay and would definitely return! The resort grounds were absolutely beautiful and impeccably maintained, and every staff member we encountered was friendly, welcoming, and helpful. We also met so many wonderful people during our stay, which made the experience even more memorable. We upgraded to a Bougainvillea Pool View room (B264), and it was worth it. I loved waking up to views of the pool with the ocean in the distance, surrounded by palm and coconut trees. The full kitchen was a huge plus, and the grills located around the pools were a great amenity for guests. The complimentary shuttle made getting around the resort easy and convenient. While the bathrooms could use a refresh, they were very clean and comfortable. Overall, this was a relaxing, well-maintained resort with excellent service, and we’d happily stay here again."

Sonesta Maho Beach All Inclusive Resort Casino & Spa

10/10 Excellent

"There were a lot of negative views regarding this resort online so I was a bit skeptical. When going in once on site it was absolutely amazing. I’m not sure where all of the negative reviews come from check-in was smooth. The property was clean. There was a lot of amenities to keep us entertained the food was good. I really enjoyed myself at this resort and will definitely be returning."

Oyster Bay Beach Resort

10/10 Excellent

"honestly, an amazing day the room stayed clean, even with how unorganized we got the ladies always came to make sure we had a clean space throughout the staff was so helpful and friendly and nice. The pool was amazing with the view. I loved it every second of the hot tub was perfect and honestly, the hotel was amazing. Only problem. I did not like the sargassum on the beach, but that is a natural problem in the hotel that their best to keep it clean."

The Westin St. Thomas Beach Resort & Spa

10/10 Excellent

"This property was perfect. There were several restaurants on and around the property with excellent food the staff was accommodating with getting taxis, shuttles etc. The pools were clean and plenty of places to sit and plenty of towels. The views were amazing from all around the property. Beautiful!! We plan to go back!!"

Emerald Beach Resort

8/10 Good

"Family of 2adults/2 teens. From the start, rent a car. The speed limit in most of the areas we visited was no more than 30MPH. It was easy to learn how to drive on the left. The hotel does not provide a shuttle service and taxis are very expensive. Free onsite parking. Once there, nothing is walkable. You’ll spend about $9/person each way to get to the charlotte Amalie area. I was hesitant to book because many reviews said the staff were rude. This is completely untrue! We got there early and could not get into our room. However, we were greeted by friendly front desk staff, given beach towels, & access to the pool. We were able to store our bags by the desk while we waited. We ate at the restaurant on site. Everyone was happy with their food. It is only steps to the sand & beach chairs were readily available. They had hoses to rinse your feet when you exit. Rooms are motel style with no elevator. Our room was very clean. This is the most important thing to us. Housekeeping was friendly and brought us extra towels and coffee when we requested them. Drinks were good at the bar and bartender was friendly. One thing you must remember, and this goes for the whole island, is “island time”. Everyone and every thing is slower than main land USA. Most things shut down by 5pm and are closed on sundays. I’m not sure I personally would classify this as a resort. However, It was very nice and we enjoyed our stay. For the price, we would absolutely stay here again."

Find Hotels with a Pool in Lesser Antilles from CA $171

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

Vieques BioBay Bed and Breakfast

Sea Gate Hotel

Nanny Cay Resort and Marina

The Moorings Yacht Club Hotel

Club Vieques - Adults Only Resort - LGBT Friendly

Old Crow Hotel and Suites

Hilton Vacation Club Flamingo Beach St. Maarten

The Cove Hotel St.Croix

Royal Islander Resort La Plage

Wyndham Tortola BVI Lambert Beach Resort

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

Hotels with pools and free breakfast in Lesser Antilles

Vieques BioBay Bed and Breakfast

4-star hotels with pools in Lesser Antilles

The Buccaneer Beach & Golf Resort

5-star hotels with pools in Lesser Antilles

Scrub Island Resort, Spa & Marina

Top Lesser Antilles Hotel Reviews

Simpson Bay Resort, Marina & Spa