Lesser Antilles Vacations 2025/2026 from CA $1,113

Name: Margaritaville Vacation Club - St. Thomas
Price range: CA $490

Lesser Antilles flight + hotel packages

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

Simpson Bay Resort, Marina & Spa

Pelican Key

CA $1,113

per person

Dec 4 - Dec 7

found 11 hours ago

Roundtrip flight included

Toronto (YTO) 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.

The Villas at Simpson Bay Resort

CA $2,690

per person

Jan 23 - Jan 30

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) 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.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

CA $1,859

per person

Jan 23 - Jan 30

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) 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.

La Playa Orient Bay

CA $2,071

per person

Dec 15 - Dec 22

found 4 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

Stay at this 4-star beach hotel in Orient Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.

Oceans at Divi Little Bay

CA $2,985

per person

Jan 23 - Jan 30

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Philipsburg (SXM)

Stay at this 4-star hotel in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Orient Bay Beach and Maho Beach are located nearby.

Top Lesser Antilles hotels deals

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road, Maho Bay, Lowlands

CA $438

per night

Nov 5 - Nov 6

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.

Pool

All-inclusive

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 $519

per night

Dec 3 - Dec 4

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.

Pool

Spa

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37, Simpson Bay

CA $166

per night

Nov 23 - Nov 24

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.

On private beach

Pool

Margaritaville Vacation Club - St. Thomas

6080 Estate Smith Bay, St. Thomas

CA $490

per night

Nov 9 - Nov 10

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.

Pool

Parking included

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 $153

per night

Nov 22 - Nov 23

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.

Pool

Parking included

The Morgan Resort Spa Village

2 Beacon Hill Road, Simpson Bay

Free cancellation

CA $386

per night

Nov 18 - Nov 19

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.

Pool

Spa

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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 relaxing 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 $1,113. 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.