Book Exclusive Lesser Antilles Vacation Packages

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Lesser Antilles flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $2,884, price is now CA $1,156 per person
CA $1,156
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
Book a stay at this 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

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $3,631, price is now CA $1,429 per person
CA $1,429
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
Book a stay at this 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 St. Martin Beaches are located nearby.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $2,308, price is now CA $1,440 per person
CA $1,440
per person
Oct 3 - Oct 9
found 2 days ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
Book a stay at this 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 Great Bay Beach and Orient Bay are located nearby.
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

5 out of 5
Price was CA $4,414, price is now CA $2,844 per person
CA $2,844
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
Book a stay at this luxury property in Lowlands. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. 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

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was CA $2,110, price is now CA $1,373 per person
CA $1,373
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
Book a stay at this 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 Maho Beach and Mullet Bay Beach are located nearby.

Top Lesser Antilles hotels deals

The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

4.5 out of 5
5 Estate Bakkeroe St. Thomas St. Thomas
The price is CA $364 per night
CA $364
CA $523 total
Sep 12 - Sep 13
includes taxes & fees
Book a stay at this 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.
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road Simpson Bay
Free cancellation
Reserve now, pay when you stay
The price is CA $656 per night
CA $656
CA $797 total
Aug 20 - Aug 21
includes taxes & fees
Book a stay at this 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.
Bluebeard's Castle Resort

Bluebeard's Castle Resort

4 out of 5
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
The price is CA $256 per night
CA $256
CA $345 total
Sep 17 - Sep 18
includes taxes & fees
Stay at this aparthotel in St. Thomas. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Magens Bay Beach and Sapphire Beach are located nearby.
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay St. Thomas
The price is CA $399 per night
CA $399
CA $449 total
Aug 21 - Aug 22
includes taxes & fees
Stay at this 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.
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
1 Rhine Road Lowlands
The price is CA $610 per night
CA $610
CA $739 total
Sep 1 - Sep 2
includes taxes & fees
Book a stay at this beach property in Lowlands. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
10 Emerald Merit Rd Oyster Pond
Free cancellation
Reserve now, pay when you stay
The price is CA $229 per night
CA $229
CA $274 total
Aug 22 - Aug 23
includes taxes & fees
Book a stay at this spa 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 and Great 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.

Stay near popular Lesser Antilles attractions

A beach with clear turquoise waters, a large airplane flying overhead, and a row of hotels in the background.

Maho Beach

8.8/10 (2,865 reviews)
Nothing says vacation like spending a lazy day at Maho Beach, a popular beach in Maho Reef. Check out the top-notch restaurants or lively bars in this romantic area.
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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 $1,156. 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.

Photos of local treasures

Browse Lesser Antilles vacation photos for more inspiration

A beach with yellow lounge chairs, palm trees, a boat, and a pier.
A beach with clear turquoise water, gentle waves, and distant mountains under a partly cloudy sky.
A beach with clear turquoise water, a palm tree, and a tire hanging from it.
A vintage yellow car parked on a cobblestone street lined with colorful buildings, including a Belgian Chocolate Box shop.
A rocky beach with large boulders, palm trees, and clear blue water.