Lesser Antilles Vacation Packages 2025/2026 from $708

Name: Sonesta Maho Beach All Inclusive Resort Casino & Spa
Price range: $283 total

Lesser Antilles flight + hotel vacation packages

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

Oyster Bay Beach Resort

Oyster Pond

Save 100% on your flight

per person

Oct 4 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

This resort features a full-service spa, a marina, and 2 restaurants. Families will appreciate the children's pool, onsite laundry facilities, and in-room childcare. Enjoy the outdoor pool and perks like free WiFi.

The Villas at Simpson Bay Resort

Save 100% on your flight

per person

Sep 6 - Sep 13

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.

Holland House Beach Hotel

Downtown Philipsburg

Save 100% on your flight

per person

Sep 6 - Sep 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

A restaurant and a bar/lounge are featured at this hotel. Dine at the beachfront restaurant and relax with beach umbrellas. WiFi in public areas is free.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

per person

Oct 4 - Oct 11

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.

Hilton Vacation Club Royal Palm St. Maarten

Save 100% on your flight

per person

Sep 6 - Sep 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free aparthotel. Enjoy the gym and perks like free self parking and free WiFi. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

Top Lesser Antilles hotels deals

The Westin St. Thomas Beach Resort & Spa

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

$402 nightly

$451 total

Sep 1 - Sep 2

Total includes 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.

Pool

Spa

Margaritaville Vacation Club - St. Thomas

6080 Estate Smith Bay, St. Thomas

$305 nightly

$343 total

Aug 6 - Aug 7

Total includes 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.

Pool

Parking included

The Morgan Resort Spa Village

2 Beacon Hill Road, Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$265 nightly

$275 total

Aug 4 - Aug 5

Total includes 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.

Pool

Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road, Maho Bay, Lowlands

$271 nightly

$283 total

Aug 18 - Aug 19

Total includes 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.

Pool

All inclusive

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37, Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$103 total

Aug 18 - Aug 19

Total includes taxes and fees

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.

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

$137 nightly

$144 total

Sep 2 - Sep 3

Total includes taxes and fees

This resort features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the gym and perks like free self parking and free WiFi. A 24-hour business center, a snack bar/deli, and laundry facilities are also on offer.

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 $708. 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.