Lesser Antilles Vacations 2026/2026 from CA $1,589

Lesser Antilles flight + hotel packages

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

Simpson Bay Resort, Marina & Spa

Pelican Key

CA $1,589

per person

Jan 21 - Jan 26

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) 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

CA $2,613

per person

Feb 6 - Feb 13

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) 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 Orient Bay Beach are located nearby.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

CA $2,285

per person

Feb 6 - Feb 13

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) 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 Orient Bay Beach and Grand Case Beach are located nearby.

Oceans at Divi Little Bay

CA $2,963

per person

Feb 6 - Feb 13

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Philipsburg (SXM)

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

Divi Little Bay Beach Resort

CA $3,104

per person

Feb 6 - Feb 13

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Philipsburg (SXM)

Book a stay at this 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.

Top Lesser Antilles hotels deals

The Morgan Resort Spa Village

2 Beacon Hill Road Simpson Bay

Free cancellation

Reserve now, pay when you stay

Get rates

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.

Pool

Spa

Margaritaville Vacation Club - St. Thomas

6080 Estate Smith Bay St. Thomas

CA $557

CA $627 total

Dec 20 - Dec 21

includes taxes & fees

Book a stay at this 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

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37 Simpson Bay

CA $348

CA $418 total

Dec 19 - Dec 20

includes taxes & fees

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.

On private beach

Pool

The Westin St. Thomas Beach Resort & Spa

5 Estate Bakkeroe St. Thomas St. Thomas

CA $997

CA $1,250 total

Jan 4 - Jan 5, 2026

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.

Pool

Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road Lowlands

CA $578

CA $699 total

Dec 21 - Dec 22

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.

Pool

All-inclusive

Jolly Beach Antigua - All-inclusive

Bolans Village, St. Mary's Jolly Harbour Antigua

CA $210

CA $302 total

Dec 20 - Dec 21

includes taxes & fees

Book a stay at this beach property in Jolly Harbour. Enjoy free parking, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Jolly Beach and Valley Church Beach are located nearby.

Pool

All-inclusive

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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

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.

Trunk Bay

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.

Orient Bay Beach

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 romantic 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 $1,589. 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.