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 $985 per person
$985
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)
Jan 18 - Jan 25
7 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Spirit Airlines • Non-stop • Coach
Price was $3,369, price is now $1,409 per person
$1,409
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
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 $4,411, price is now $1,978 per person
$1,978
per person
found 1 day ago
Balcony was a beautiful view
Reviewed on Oct 29, 2025
4.0-star property
Divi Little Bay Beach Resort
8.4/10 Very Good! (1,002 reviews)
Jan 18 - Jan 25
7 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Spirit Airlines • Non-stop • Coach
Price was $3,578, price is now $2,159 per person
$2,159
per person
found 1 day ago
Nice grounds, well kept and maintained. Beautiful property.
Reviewed on Apr 1, 2025
4.0-star property
Holland House Beach Hotel
Downtown Philipsburg
9.2/10 Wonderful! (1,002 reviews)
Mar 6 - Mar 13
7 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,426, price is now $2,089 per person
$2,089
per person
found 1 day ago
The staff are amazing and it is super convenient to stores.
Breakfast was great!
Reviewed on Sep 5, 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
$359 nightly
The price is $373 total per night
$373 total
Dec 16 - Dec 17
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
$314 nightly
The price is $354 total per night
$354 total
Dec 16 - Dec 17
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 16 - Dec 17
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.
