Name: Simpson Bay Resort, Marina & Spa
Price range: $167 total
Rating: 8.8

Your Lesser Antilles Vacation

See and do more with a vacation package to Lesser Antilles. Whether you're going for the views, history, culture, or something else, our package deals make travel planning easy. With so many things to explore on a trip to Lesser Antilles, it can be difficult to know where to start. Kick off your journey in Charlotte Amalie at Bolongo Bay and Magens Bay Beach — two popular attractions here. Another great city to add to your itinerary is Philipsburg. Be sure not to miss Maho Beach and Great Bay Beach. Start packing your suitcase, because your Lesser Antilles vacation is just a few clicks away with Expedia.

The Latest Lesser Antilles vacation packages

Price found within the past 48 hours. Click for updated prices.

Sapphire Beach Club Resort

Maho

$518

per person

Jan 23 - Jan 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

14/10 Exceptional! (690 reviews)

Clean and very respectful staff

Reviewed on Nov 8, 2025

Simpson Bay Resort, Marina & Spa

Pelican Key

$562

per person

Jan 27 - Jan 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

18/10 Exceptional! (1,453 reviews)

Our room was excellent and everyone so sweet and friendly everywhere we went! We will definitely be back at this resort but for longer than a week next time. Until we see tou again! Thanks so much for an unforgettable time

Reviewed on Nov 15, 2025

The Villas at Simpson Bay Resort

$969

per person

Jan 19 - Jan 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

18.4/10 Exceptional! (1,304 reviews)

Was very convenient and staff were wonderful. Ate at the sports bar almost every night. Staff there are excellent

Reviewed on Nov 15, 2025

Panorama Residences at Monte Vista

Point Blanche

Save 100% on your flight

$623

per person

Jan 23 - Jan 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

No reviews

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

$669

per person

Jan 23 - Jan 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

18.4/10 Exceptional! (972 reviews)

Very helpful front desk staff. Wonderful ocean view. Very clean room!!

Reviewed on Nov 12, 2025

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Where to stay in Lesser Antilles

Find the best Lesser Antilles areas and neighborhoods for the activities you enjoy most. Learn more about Lesser Antilles

Mullet Bay Beach which includes a beach, tropical scenes and general coastal views

Maho

4/5(279 area reviews)

Along with restaurants, resorts and shops just steps from soft, white sand, this beachfront neighborhood offers the thrilling experience of plane spotting.

Discover the most popular places to visit in Lesser Antilles

Sapphire Beach

4.5/5(258 reviews)

Enjoy sunbathing, swimming and fun-filled watersports at this peaceful arched bay.

Orient Bay Beach

4/5(365 reviews)

Pack your sunscreen, grab your swimsuit and head for a coastal gem known as the Saint- Tropez of the Caribbean.

Trunk Bay

4.5/5(356 reviews)

Backed by palms, this stretch of sparkling white sand is regularly ranked as one of the most beautiful beaches in the world.

Lesser Antilles Hotel Deals

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road Lowlands

$362 nightly

$378 total

Nov 18 - Nov 19

Total with taxes and fees

7.8/10 Good! (2,695 reviews)

I loved everything about this resort. The front desk staff was excellent, especially Enrique. The dining room staff was also friendly. The premise was clean and well-kept. My only complaint is, there seems to be a smell close to the children's camp by the pool area. Overall, it was worth every ...

Reviewed on Nov 10, 2025

The Westin St. Thomas Beach Resort & Spa

5 Estate Bakkeroe, Po Box 7100, St. Thomas, St. Thomas

$492 nightly

$552 total

Nov 17 - Nov 18

Total with taxes and fees

8.2/10 Very Good! (1,007 reviews)

Swim up bar was fun, the view was amazing. Roan was amazing getting our car for us as well as Lea. Loved them. My only suggestion would be to have the bar open a little earlier.

Reviewed on Nov 14, 2025

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37 Simpson Bay

Fully refundableReserve now, pay when you stay

$160 nightly

$167 total

Dec 11 - Dec 12

Total with taxes and fees

8.8/10 Excellent! (1,463 reviews)

The breakfast menu was fresh and so was the lunch buffet. The room was clean and the staff courteous and friendly.

Reviewed on Nov 14, 2025

See all 14,771 properties in Lesser Antilles

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.