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.
4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (1,345 reviews)
Nov 21 - Nov 26
5 night stay
Boston (BOS) to Philipsburg (SXM)
Air Canada • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Delta • Non-stop • Coach
Save 100% on your flight
Price was $1,227, price is now $723 per person
$723
per person
found 1 day ago
I had an excellent time, everything was perfect. Staff were polite and very helpful. 5 star experience.
Reviewed on Jul 31, 2025
4.0-star property
The Villas at Simpson Bay Resort
9.2/10 Wonderful! (1,241 reviews)
Oct 24 - Oct 29
5 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
United • Non-stop • Coach
Save 100% on your flight
Price was $1,340, price is now $787 per person
$787
per person
found 1 day ago
Had a great time! Room clean and updated. Great staff and location!!
Reviewed on Aug 4, 2025
4.0-star property
La Playa Orient Bay
9.4/10 Exceptional! (592 reviews)
Nov 21 - Nov 25
4 night stay
Boston (BOS) to Philipsburg (SXM)
Air Canada • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
United • Non-stop • Coach
Save 100% on your flight
Price was $1,404, price is now $947 per person
$947
per person
found 1 day ago
All the folks working at this property were great. The resort was nice but not pretentious.
Reviewed on Nov 18, 2024
4.0-star property
Oyster Bay Beach Resort
Oyster Pond
8.6/10 Excellent! (932 reviews)
Oct 24 - Oct 29
5 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
United • Non-stop • Coach
Price was $1,050, price is now $732 per person
$732
per person
found 1 day ago
Beautiful area on St Maarten. Peaceful, serene, quiet, gorgeous views of the ocean, St Barts, and the mountains of the island
Reviewed on Jul 20, 2025
4.0-star property
Holland House Beach Hotel
Downtown Philipsburg
9.2/10 Wonderful! (1,004 reviews)
Nov 21 - Nov 25
4 night stay
Boston (BOS) to Philipsburg (SXM)
Air Canada • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
United • Non-stop • Coach
Save 100% on your flight
Price was $1,462, price is now $1,032 per person
$1,032
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
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37, Simpson Bay
Free Cancellation
Reserve now, pay when you stay
28.64 mi from city center
$116 nightly
The price is $121 total per night
$121 total
Oct 6 - Oct 7
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 luggage storage, concierge services, and securing valuables. Other amenities at this beach resort include 6 outdoor pools, a children's pool, and a gym.
On private beach
Pool
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road, Maho Bay, Lowlands
27.74 mi from city center
$241 nightly
The price is $252 total per night
$252 total
Sep 22 - Sep 23
Total with taxes and fees
Sonesta Maho Beach All Inclusive Resort Casino & Spa features a full-service spa, 2 outdoor pools, and a casino. Self parking is offered for USD 10 per day. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, luggage storage, and dry cleaning/laundry. Other amenities at this all-inclusive property include a free water park, karaoke, and a children's pool.
Pool
All inclusive
Margaritaville Vacation Club - St. Thomas
6080 Estate Smith Bay, St. Thomas
99.41 mi from city center
$251 nightly
The price is $282 total per night
$282 total
Sep 23 - Sep 24
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
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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.
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