
Lesser Antilles Vacations from $599
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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


Simpson Bay Resort, Marina & Spa
Reviewed on Nov 9, 2025

The Villas at Simpson Bay Resort
Reviewed on Nov 9, 2025

Princess Heights Luxury Boutique Condo Hotel
Reviewed on Nov 10, 2025

Oceans at Divi Little Bay
Reviewed on Oct 23, 2025
Where to stay in Lesser Antilles

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

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

Maho Beach
Why not spend a carefree afternoon at Maho Beach during your travels in Maho Reef? Check out the lively bars or top-notch restaurants in this family-friendly area.
Lesser Antilles Hotel Deals

Sonesta Maho Beach All Inclusive Resort Casino & Spa
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
Was very prompt and courteous
Reviewed on Nov 8, 2025

Simpson Bay Resort, Marina & Spa
Most for your buck
Reviewed on Nov 8, 2025























