Lesser Antilles Vacations from $752

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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.
Simpson Bay Resort, Marina & Spa
The Villas at Simpson Bay Resort
Hilton Vacation Club Royal Palm St. Maarten
Holland House Beach Hotel
La Playa Orient Bay
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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

Discover the most popular places to visit in Lesser Antilles

Lesser Antilles Hotel Deals

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37, Simpson Bay
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $124 total per night from Oct 22 to Oct 23
$124 total
Oct 22 - Oct 23
Total with taxes and fees
8.8/10 Excellent! (1,366 reviews)
"They need some shuttles on property to move around."

Reviewed on Oct 1, 2025

Simpson Bay Resort, Marina & Spa
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
1 Rhine Road, Maho Bay, Lowlands
$221 nightly
The price is $231 total per night from Oct 6 to Oct 7
$231 total
Oct 6 - Oct 7
Total with taxes and fees
7.8/10 Good! (2,620 reviews)
"The spa was relaxing i enjoyed maho beach and seeing the planes take off however the dinner food was nasty i didn't like it or enjoy it"

Reviewed on Sep 26, 2025

Sonesta Maho Beach All Inclusive Resort Casino & Spa
Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

4 out of 5
Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $119 total per night from Oct 9 to Oct 10
$119 total
Oct 9 - Oct 10
Total with taxes and fees
9/10 Wonderful! (1,259 reviews)
"The check in staff were very friendly. However the pool bar female wo"

Reviewed on Sep 30, 2025

Hilton Vacation Club Flamingo Beach St. Maarten
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.