Deals on vacations and trips to Lesser Antilles
Save when you book Lesser Antilles package deals
Lesser Antilles flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Save 100% on your flight
Price was $1,052, price is now $564 per person
$564
per person
May 16 - May 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.
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was $2,338, price is now $980 per person
$980
per person
May 16 - May 23
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.
The Villas at Simpson Bay Resort
Pelican Key
Save 100% on your flight
Price was $1,365, price is now $660 per person
$660
per person
May 16 - May 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.
La Playa Orient Bay
Save 100% on your flight
Price was $1,123, price is now $678 per person
$678
per person
May 16 - May 20
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.
Panorama Residences at Monte Vista
Point Blanche
Save 100% on your flight
Price was $1,259, price is now $772 per person
$772
per person
May 16 - May 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A terrace, a garden, and a virtual front desk are also on offer.
Top Lesser Antilles hotels deals
Bluebeard's Castle Resort
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
$257 nightly
The price is $286 total per night
$286 total
Apr 12 - Apr 13
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
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
Free Cancellation
Reserve now, pay when you stay
$496 nightly
The price is $517 total per night
$517 total
Apr 1 - Apr 2
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
Margaritaville Vacation Club - St. Thomas
6080 Estate Smith Bay St. Thomas
$593 nightly
The price is $667 total per night
$667 total
Mar 14 - Mar 15
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
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road Lowlands
$563 nightly
The price is $587 total per night
$587 total
Apr 1 - Apr 2
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
All inclusive
The Westin St. Thomas Beach Resort & Spa
5 Estate Bakkeroe St. Thomas St. Thomas
$785 nightly
The price is $881 total per night
$881 total
Apr 5 - Apr 6
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
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
$373 nightly
The price is $392 total per night
$392 total
Apr 10 - Apr 11
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
Don't see what you're looking for?
See all available properties in Lesser Antilles
View all propertiesLowest 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
4.5/5(258 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 family-friendly area.
Maho Beach
4/5(445 reviews)
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
4.5/5(356 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.
Frequently asked questions
Photos of local treasures
Browse Lesser Antilles vacation photos for more inspiration
