Deals on vacations and trips to Lesser Antilles

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Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was $902, price is now $570 per person
$570
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $2,297, price is now $1,014 per person
$1,014
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
Price was $1,309, price is now $676 per person
$676
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was $889, price is now $618 per person
$618
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

4 out of 5
Oyster Pond
Save 100% on your flight
Price was $1,578, price is now $1,098 per person
$1,098
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Philipsburg (SXM)
This Mediterranean resort features a full-service spa, a marina, and 2 restaurants. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare.

Top Lesser Antilles hotels deals

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road Simpson Bay
Free Cancellation
Reserve now, pay when you stay
$378 nightly
The price is $393 total per night
$393 total
Jul 29 - Jul 30
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.
Pool
Spa
The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

4.5 out of 5
5 Estate Bakkeroe St. Thomas St. Thomas
$415 nightly
The price is $467 total per night
$467 total
Jul 26 - Jul 27
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.
Pool
Spa
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
1 Rhine Road Lowlands
$451 nightly
The price is $470 total per night
$470 total
Jun 29 - Jun 30
Total with taxes and fees
This 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
Spa
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay St. Thomas
$341 nightly
The price is $384 total per night
$384 total
Jun 30 - Jul 1
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.
Pool
Parking included
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
Free Cancellation
Reserve now, pay when you stay
$272 nightly
The price is $285 total per night
$285 total
Jul 1 - Jul 2
Total with 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
Bluebeard's Castle Resort

Bluebeard's Castle Resort

4 out of 5
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
$220 nightly
The price is $249 total per night
$249 total
Jul 27 - Jul 28
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.
Pool
Hot Tub
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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

A beach with clear turquoise water, a large tree, and a distant hill with buildings.

Sapphire Beach

4.5/5(261 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 romantic area.

Sapphire Beach
A tropical beach with clear turquoise waters, lush green hills, and a small red building on a hill.

Trunk Bay

4.5/5(358 reviews)

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.

Trunk Bay
A beach with turquoise water, white sand, and two beach umbrellas.

Orient Bay Beach

4/5(371 reviews)

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.

Orient Bay Beach

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 $570. 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.

Photos of local treasures

Browse Lesser Antilles vacation photos for more inspiration

A beach with yellow lounge chairs, palm trees, a boat, and a pier.
A beach with clear turquoise water, gentle waves, and distant mountains under a partly cloudy sky.
A beach with clear turquoise water, a palm tree, and a tire hanging from it.
A vintage yellow car parked on a cobblestone street lined with colorful buildings, including a Belgian Chocolate Box shop.
A rocky beach with large boulders, palm trees, and clear blue water.