Lesser Antilles Vacation Packages
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Top Lesser Antilles vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (973 reviews)
Apr 11 - Apr 16
5 night stay
Boston (BOS) to Philipsburg (SXM)
JetBlue Airways • Roundtrip • Coach
Price was $1,610, price is now $997 per person
$997
per person
found 1 day ago
The room was spacious, clean and had adequate storage. The kitchenette was properly outfitted and they gave us a few complimentary drinks, The place was very quiet and private.
Reviewed on Nov 26, 2025
4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (1,463 reviews)
Apr 11 - Apr 16
5 night stay
Boston (BOS) to Philipsburg (SXM)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $2,301, price is now $1,165 per person
$1,165
per person
found 1 day ago
Great staff, comfortable rooms,walking distance to many restaurants....
Reviewed on Nov 10, 2025
4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,309 reviews)
Mar 20 - Mar 23
3 night stay
Boston (BOS) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to Boston (BOS)
American Airlines • Coach
Save 100% on your flight
Price was $2,185, price is now $1,248 per person
$1,248
per person
found 1 day ago
Balcony was a beautiful view
Reviewed on Oct 29, 2025
4.0-star property
La Playa Orient Bay
9.4/10 Exceptional! (604 reviews)
Apr 10 - Apr 14
4 night stay
Boston (BOS) to Philipsburg (SXM)
Air Canada • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,651, price is now $1,038 per person
$1,038
per person
found 2 hours ago
All the folks working at this property were great. The resort was nice but not pretentious.
Reviewed on Nov 18, 2024
Top rated hotels for your Lesser Antilles vacation package
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
27.59 mi from city center
$479 nightly
The price is $500 total per night
$500 total
Feb 15 - Feb 16
Total with taxes and fees
At The Morgan Resort Spa Village, guests enjoy a full-service spa, an outdoor pool, and a gym. Free valet and self parking are available—or if you're not driving, take the free airport shuttle (available 24 hours). The front desk has multilingual staff on hand 24/7 to help with tours or tickets, luggage storage, and securing valuables. Other amenities at this spa resort include free WiFi in public areas, free newspapers, and a terrace.
Margaritaville Vacation Club - St. Thomas
6080 Estate Smith Bay St. Thomas
99.41 mi from city center
$629 nightly
The price is $708 total per night
$708 total
Feb 9 - Feb 10
Total with taxes and fees
Guests staying at Margaritaville Vacation Club - St. Thomas enjoy access to 2 outdoor pools, a gym, and free WiFi in public areas. You can take advantage of free parking, along with a shopping center shuttle. The front desk has multilingual staff standing by 24 hours a day to assist with tours/tickets and luggage storage. Other amenities at this beach hotel include a computer station, a terrace, and laundry facilities.
Pool
Parking included
Bluebeard's Castle Resort
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
102.67 mi from city center
$252 nightly
The price is $281 total per night
$281 total
Feb 9 - Feb 10
Total with taxes and fees
Guests of Bluebeard's Castle Resort have access to an outdoor pool, a gym, and free WiFi in public areas. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Additional amenities include a hot tub and laundry facilities.
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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.
