Lesser Antilles Vacation Packages 2026 from $778

Lesser Antilles flight + hotel vacation packages

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

La Playa Orient Bay

Save 100% on your flight

$778

per person

May 25 - May 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Families will appreciate the onsite laundry facilities and in-room childcare.

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

$1,302

per person

Jun 14 - Jun 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

A marina, 3 restaurants, and 6 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a waterslide, and barbecue grills are available on site.

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

$1,199

per person

Jun 14 - Jun 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

This smoke-free resort features a private beach, a full-service spa, and a marina. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

$989

per person

Jun 14 - Jun 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

This hotel features an outdoor pool and a 24-hour gym. Families will appreciate the waterslide, onsite laundry facilities, and in-room childcare. Guests will appreciate free perks like free self parking and WiFi in public areas.

Sonesta Ocean Point All Inclusive, Adults Only Resort

Save 100% on your flight

$2,240

per person

May 28 - May 31

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

This smoke-free property features a casino, a full-service spa, and 3 restaurants. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. Enjoy the 3 outdoor pools and perks like free WiFi.

Top Lesser Antilles hotels deals

Bluebeard's Castle Resort

1331 Estate Taarneberg Charlotte Amalie Saint Thomas

$313 nightly

$349 total

Apr 20 - Apr 21

Total with taxes and fees

This hotel features an outdoor pool, a hot tub, and a restaurant. Enjoy the gym and perks like free WiFi. A bar/lounge, a poolside bar, and a coffee shop are also provided.

The Morgan Resort Spa Village

2 Beacon Hill Road Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$490 nightly

$511 total

Apr 5 - Apr 6

Total with taxes and fees

A full-service spa, an outdoor pool, and a restaurant are all featured at this resort. Enjoy the gym and perks like free valet parking and a free airport shuttle. There's a bar/lounge on site, and concierge services and free newspapers are also provided.

Margaritaville Vacation Club - St. Thomas

6080 Estate Smith Bay St. Thomas

$674 nightly

$758 total

Mar 24 - Mar 25

Total with taxes and fees

This smoke-free hotel features 2 outdoor pools, a gym, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Relax with a drink at one of the 2 poolside bars and enjoy free perks like free self parking and WiFi in public areas.

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road Lowlands

$469 nightly

$489 total

Apr 1 - Apr 2

Total with taxes and fees

This all-inclusive property features free water park access, a casino, and a full-service spa. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a free kid's club and a children's pool, and free supervised childcare is an added bonus.

The Westin St. Thomas Beach Resort & Spa

5 Estate Bakkeroe St. Thomas St. Thomas

$707 nightly

$794 total

Apr 19 - Apr 20

Total with taxes and fees

A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this luxury resort. Enjoy a day at the beach kayaking, or relax with beach cabanas. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37 Simpson Bay

$280 nightly

$294 total

Apr 21 - Apr 22

Total with taxes and fees

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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 family-friendly area.

Maho Beach

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.

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.

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 $778. 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.