Lesser Antilles Vacations 2025 from CA $870

Lesser Antilles flight + hotel packages

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

The Villas at Simpson Bay Resort

Save 100% on your flight

per person

May 9 - May 12

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.

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

per person

May 11 - May 18

found 4 hours ago

Roundtrip flight included

Toronto (YYZ) 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.

Villa Amalia

Save 100% on your flight

per person

Jun. 1 - Jun. 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Philipsburg (SXM)

Stay at this 5-star luxury vacation home in Philipsburg. Enjoy free WiFi, free parking, and private pools. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.

La Playa Orient Bay

Save 100% on your flight

per person

May 10 - May 16

found 1 day ago

Roundtrip flight included

Edmonton (YEG) 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.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

per person

May 19 - May 24

found 1 day ago

Roundtrip 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.

Top Lesser Antilles hotels deals

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road, Maho Bay, Lowlands

CA $364

per night

Mar. 31 - Apr. 1

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.

Margaritaville Vacation Club - St. Thomas

6080 Estate Smith Bay, St. Thomas

CA $591

per night

Apr. 1 - Apr. 2

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

The Morgan Resort Spa Village

2 Beacon Hill Road, Simpson Bay

Free cancellation

Reserve now, pay when you stay

CA $444

per night

Mar. 30 - Mar. 31

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

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37, Simpson Bay

Free cancellation

Reserve now, pay when you stay

CA $181

per night

Apr. 29 - Apr. 30

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.

Windward Passage Hotel

Veterans Drive Charlotte Amali, Po Box 640, St. Thomas, St. Thomas

Free cancellation

Reserve now, pay when you stay

CA $309

per night

Apr. 5 - Apr. 6

Stay at this 3.5-star hotel in St. Thomas. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sapphire Beach and Magens Bay Beach are located nearby.

Hilltop Villas at Bluebeard's Castle

1331 Estate Taarneberg, Bluebeard Loop, St. Thomas, St. Thomas

CA $297

per night

Apr. 6 - Apr. 7

Stay at this 3-star aparthotel in St. Thomas. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Sapphire Beach and Magens Bay Beach are located nearby.

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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.

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.

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 lively bars or top-notch restaurants in this walkable 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 $870. 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.