Lesser Antilles Vacations 2025 from CA $670

Lesser Antilles flight + hotel packages

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

Simpson Bay Resort, Marina & Spa

Pelican Key

per person

Jun. 12 - Jun. 15

found 23 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

Save 100% on your flight

per person

Jun. 12 - Jun. 15

found 23 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 Orient Bay Beach are located nearby.

La Playa Orient Bay

Save 100% on your flight

per person

May 17 - May 24

found 11 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) 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.

Divi Little Bay Beach Resort

Save 100% on your flight

per person

Jun. 12 - Jun. 15

found 23 hours ago

Roundtrip flight included

Toronto (YTO) to Philipsburg (SXM)

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

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

per person

May 17 - May 24

found 11 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) 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 $290

CA $351 total

includes taxes & fees

May 6 - May 7

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

Breakfast included

Margaritaville Vacation Club - St. Thomas

6080 Estate Smith Bay, St. Thomas

CA $501

CA $564 total

includes taxes & fees

Apr 17 - Apr 18

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.

The Morgan Resort Spa Village

2 Beacon Hill Road, Simpson Bay

Free cancellation

Reserve now, pay when you stay

CA $496

CA $618 total

includes taxes & fees

Apr 20 - Apr 21

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.

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37, Simpson Bay

Free cancellation

Reserve now, pay when you stay

CA $171

CA $205 total

includes taxes & fees

May 15 - May 16

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 Westin St. Thomas Beach Resort & Spa

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

CA $546

CA $749 total

includes taxes & fees

May 15 - May 16

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.

Windward Passage Hotel

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

Free cancellation

Reserve now, pay when you stay

CA $300

CA $368 total

includes taxes & fees

Apr 17 - Apr 18

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.

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 top-notch restaurants or lively bars in this romantic 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 top-notch restaurants or lively bars in this quaint 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 $670. 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.