Lesser Antilles Vacations 2025/2026 from CA $913

Name: Margaritaville Vacation Club - St. Thomas
Price range: CA $346

Lesser Antilles flight + hotel packages

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

Oyster Bay Beach Resort

Oyster Pond

CA $913

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

Stay at this 4-star beach resort in Oyster Pond. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.

The Villas at Simpson Bay Resort

CA $970

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

Stay at this 4-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Orient Bay Beach and Maho Beach are located nearby.

Simpson Bay Resort, Marina & Spa

Pelican Key

CA $1,226

per person

Nov 2 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

Stay at this 4-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

Holland House Beach Hotel

Downtown Philipsburg

CA $2,034

per person

Nov 22 - Nov 29

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Philipsburg (SXM)

Stay at this 4-star beach hotel in Philipsburg. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Orient Bay Beach and Maho Beach are located nearby.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

CA $1,294

per person

Dec 3 - Dec 9

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

Stay at this 3.5-star family-friendly hotel in Oyster Pond. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.

Top Lesser Antilles hotels deals

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road, Maho Bay, Lowlands

CA $286

CA $346 total

Sep 22 - Sep 23

includes taxes & fees

Stay at this 4-star beach property in Lowlands. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

Margaritaville Vacation Club - St. Thomas

6080 Estate Smith Bay, St. Thomas

CA $346

CA $389 total

Sep 23 - Sep 24

includes taxes & fees

Stay at this 4-star beach hotel in St. Thomas. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Sapphire Beach and Magens Bay Beach are located nearby.

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37, Simpson Bay

Free cancellation

Reserve now, pay when you stay

CA $139

CA $167 total

Sep 30 - Oct 1

includes taxes & fees

Stay at this 4-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay

Free cancellation

Reserve now, pay when you stay

CA $106

CA $148 total

Sep 24 - Sep 25

includes taxes & fees

Stay at this 4-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

The Morgan Resort Spa Village

2 Beacon Hill Road, Simpson Bay

Get rates

Stay at this 4-star spa resort in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

The Westin St. Thomas Beach Resort & Spa

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

Free cancellation

Reserve now, pay when you stay

CA $330

CA $482 total

Oct 1 - Oct 2

includes taxes & fees

Stay at this 4.5-star luxury resort in St. Thomas. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Magens Bay Beach and Sapphire Beach are located nearby.

Don't see what you're looking for?

See all available properties in Lesser Antilles

View all properties

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.

Popular places to visit

Sapphire Beach

4.5/5(5 reviews)

Nothing says vacation like spending a lazy day at Sapphire Beach, a popular beach in Red Hook. You can seek out the snorkeling spots in this romantic area.

Magens Bay Beach

5/5(8 reviews)

Nothing says vacation like spending a lazy day at Magens Bay Beach, a popular beach in St. Thomas. Stroll along the waterfront in this romantic area, or seek out the snorkeling spots.

Orient Bay Beach

4/5(65 reviews)

Nothing says vacation like spending a lazy day at Orient Bay Beach, a popular beach in Orient Bay. Check out the top-notch restaurants or lively bars in this romantic area.

Frequently asked questions

How much are vacation packages to Lesser Antilles?

Splash out on a memorable travel experience in Lesser Antilles with a vacation package starting from just CA $913. Reserving flights and hotels through Travelocity is a piece of cake. What's more, our great deals will leave you with extra cash for fun, fun, fun!

Where can I get the best vacation package deals for Lesser Antilles?

It's hard to top Travelocity when it comes to piecing together your Lesser Antilles package deal. There are as many as 400 partner airlines and 1,000,000 properties worldwide to select from. Book your vacation now and get ready to cross another destination off your travel bucket list.

Why should I book my Lesser Antilles vacation package via Travelocity?

With our Price Match Guarantee, we'll match any cheaper price you're able to find. Add to that our 24/7 customer support and top-shelf service and the vacation of your dreams is closer than ever before.

Will I save money on my Lesser Antilles car rental if I book it with hotels and flights?

Combining your bookings into a Lesser Antilles vacation package will certainly save you money. You can book a car and flight; a hotel, flight and car; or a car and hotel. There's no better way to discover the greater Lesser Antilles area than from the comfort of your own rental car. You can also add activities and experiences to your Travelocity package.

Which airport is best for Lesser Antilles?

Princess Juliana Intl. Airport (SXM) is a popular option for visitors flying to Lesser Antilles. Robert L. Bradshaw Intl. Airport (SKB) and Clayton J. Lloyd Intl. Airport (AXA) also welcome many of the region's flights.

What is there to do in Lesser Antilles?

You'll be happy to know Lesser Antilles is full of terrific photo-ops, however Dickenson Bay Beach and The Baths are among the best of them.