Lesser Antilles Vacations 2025/2026 from CA $1,055

Name: Sonesta Maho Beach All Inclusive Resort Casino & Spa
Price range: CA $323

Lesser Antilles flight + hotel packages

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

Cozy one-bedroom & mezzanine apartment

Point Blanche

per person

Sep 14 - Sep 21

found 9 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Philipsburg (SXM)

Stay at this 3-star apartment in Philipsburg. Enjoy free WiFi, an airport shuttle (surcharge), and balconies. Popular attractions Maho Beach and Orient Bay Beach are located nearby.

La Playa Orient Bay

per person

Oct 19 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) 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.

Dawn Beach Club Resort Sint Maarten

Oyster Pond

per person

Sep 14 - Sep 21

found 9 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Philipsburg (SXM)

Stay at this 4-star beach condo in Oyster Pond. Enjoy free parking, 2 restaurants, and a beach locale. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.

Aqua Vue by Island Properties Online

Maho

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Philipsburg (SXM)

Stay at this 3.5-star condo in Lowlands. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Mullet Bay Beach and Maho Beach are located nearby.

Alizee by Island Properties Online

per person

Sep 14 - Sep 21

found 12 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Philipsburg (SXM)

Stay at this 3.5-star villa in Philipsburg. Enjoy free WiFi, free parking, and a garden. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.

Top Lesser Antilles hotels deals

The Westin St. Thomas Beach Resort & Spa

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

CA $451

CA $622 total

Sep 1 - Sep 2

includes taxes & fees

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 Magens Bay Beach and Sapphire Beach are located nearby.

Pool

Spa

Margaritaville Vacation Club - St. Thomas

6080 Estate Smith Bay, St. Thomas

CA $421

CA $473 total

Aug 6 - Aug 7

includes taxes & fees

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 Magens Bay 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

Get rates

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

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road, Maho Bay, Lowlands

CA $323

CA $390 total

Aug 18 - Aug 19

includes taxes & fees

Stay at this 4-star beach property in Lowlands. Enjoy free WiFi, 2 outdoor pools, 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

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37, Simpson Bay

Free cancellation

Reserve now, pay when you stay

CA $90

CA $109 total

Aug 18 - Aug 19

includes taxes & fees

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

CA $155

CA $199 total

Sep 2 - Sep 3

includes taxes & fees

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

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.

Magens Bay Beach

Nothing says vacation like spending a lazy day at Magens Bay Beach, a popular beach in St. Thomas. Stroll along the seaside in this romantic area, 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 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 $1,055. 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.