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)
Oct 29 - Nov 3
5 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,026, price is now $625 per person
$625
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 29 - Nov 3
5 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,283, price is now $727 per person
$727
per person
found 1 day ago
Had a great time! Room clean and updated. Great staff and location!!
Reviewed on Aug 4, 2025
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (964 reviews)
Dec 4 - Dec 8
4 night stay
Boston (BOS) to Philipsburg (SXM)
Air Canada • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Spirit Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,138, price is now $757 per person
$757
per person
found 1 day ago
Overall a great choice to stay
Reviewed on Feb 18, 2025
4.0-star property
Holland House Beach Hotel
Downtown Philipsburg
9.2/10 Wonderful! (1,004 reviews)
Nov 9 - Nov 15
6 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,360, price is now $1,591 per person
$1,591
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
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 $1,397, price is now $946 per person
$946
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
Top rated hotels for your Lesser Antilles vacation package
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.
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
Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay
Free Cancellation
Reserve now, pay when you stay
28.62 mi from city center
$108 nightly
The price is $113 total per night
$113 total
Sep 25 - Sep 26
Total with taxes and fees
At Hilton Vacation Club Flamingo Beach St. Maarten, guests enjoy an outdoor pool, a gym, and free WiFi in public areas. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Other amenities at this beach resort include a 24-hour business center, laundry facilities, and a porter/bellhop.
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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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