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)
Feb 27 - Mar 6
7 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,876, price is now $998 per person
$998
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
The Villas at Simpson Bay Resort
9.2/10 Wonderful! (1,309 reviews)
Feb 27 - Mar 6
7 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
American Airlines • Non-stop • Coach
Price was $4,223, price is now $2,020 per person
$2,020
per person
found 1 day ago
Balcony was a beautiful view
Reviewed on Oct 29, 2025
4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (1,463 reviews)
Mar 6 - Mar 11
5 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,434, price is now $1,248 per person
$1,248
per person
found 19 hours ago
Great staff, comfortable rooms,walking distance to many restaurants....
Reviewed on Nov 10, 2025
4.0-star property
Divi Little Bay Beach Resort
8.4/10 Very Good! (1,002 reviews)
Jan 31 - Feb 6
6 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,889, price is now $1,754 per person
$1,754
per person
found 1 day ago
Nice grounds, well kept and maintained. Beautiful property.
Reviewed on Apr 1, 2025
4.0-star property
Oceans at Divi Little Bay
8.4/10 Very Good! (266 reviews)
Feb 27 - Mar 6
7 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $3,212, price is now $2,078 per person
$2,078
per person
found 1 day ago
Great property for families
Reviewed on Jul 31, 2025
Top rated hotels for your Lesser Antilles vacation package
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
Free Cancellation
Reserve now, pay when you stay
27.59 mi from city center
$401 nightly
The price is $418 total per night
$418 total
Jan 15 - Jan 16, 2026
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.
Pool
Spa
Margaritaville Vacation Club - St. Thomas
6080 Estate Smith Bay St. Thomas
99.41 mi from city center
$329 nightly
The price is $370 total per night
$370 total
Dec 18 - Dec 19
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 luggage storage and tours/tickets. Other amenities at this beach hotel include a computer station, a terrace, and laundry facilities.
Pool
Parking included
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
28.64 mi from city center
$266 nightly
The price is $278 total per night
$278 total
Dec 18 - Dec 19
Total with taxes and fees
Simpson Bay Resort, Marina & Spa features a private beach, a marina, and a full-service spa. If you plan to drive, free parking is available. The front desk has multilingual staff on hand 24/7 to help with concierge services, securing valuables, and luggage storage. Other amenities at this beach resort include 6 outdoor pools, a children's pool, and a gym.
On private beach
Pool
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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.
