Lesser Antilles Vacations 2025 from CA $1,137

Lesser Antilles flight + hotel packages

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

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

per person

Aug 30 - Sep 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) 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.

The Villas at Simpson Bay Resort

Save 100% on your flight

per person

Jul 18 - Jul 25

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) 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 Orient Bay Beach are located nearby.

Holland House Beach Hotel

Downtown Philipsburg

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per person

Aug 30 - Sep 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) 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.

The Morgan Resort Spa Village

Save 100% on your flight

per person

Aug 30 - Sep 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Philipsburg (SXM)

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.

Oyster Bay Beach Resort

Oyster Pond

Save 100% on your flight

per person

Aug 30 - Sep 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) 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.

Top Lesser Antilles hotels deals

The Morgan Resort Spa Village

2 Beacon Hill Road, Simpson Bay

Free cancellation

Reserve now, pay when you stay

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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

Margaritaville Vacation Club - St. Thomas

6080 Estate Smith Bay, St. Thomas

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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 Coki Point Beach are located nearby.

Pool

Parking included

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road, Maho Bay, Lowlands

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Stay at this 4-star beach property in Lowlands. Enjoy free breakfast, free WiFi, 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

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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 Sapphire Beach and Bolongo Bay are located nearby.

Pool

Spa

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37, Simpson Bay

Free cancellation

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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

Hilton Vacation Club Flamingo Beach St. Maarten

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

Free cancellation

Reserve now, pay when you stay

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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

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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 family-friendly area.

Maho Beach

4/5(61 reviews)

Nothing says vacation like spending a lazy day at Maho Beach, a popular beach in Maho Reef. Check out the lively bars or top-notch restaurants in this family-friendly area.

Trunk Bay

5/5(5 reviews)

Nothing says vacation like spending a lazy day at Trunk Bay, a popular beach in St. John. Amble around the area's seaside or seek out the snorkeling spots.

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 $1,137. 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.