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! (1,981 reviews)
Oct 30 - Nov 2
3 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Coach
Philipsburg (SXM) to Boston (BOS)
Southwest Airlines • Coach
Save 100% on your flight
Price was $1,171, price is now $632 per person
$632
per person
found 1 day ago
N/A
Reviewed on Aug 29, 2026
4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,519 reviews)
Oct 30 - Nov 2
3 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Coach
Philipsburg (SXM) to Boston (BOS)
Southwest Airlines • Coach
Save 100% on your flight
Price was $1,319, price is now $673 per person
$673
per person
found 1 day ago
4.0-star property
Coral Beach Club Villas & Marina
Oyster Pond
9.2/10 Wonderful! (119 reviews)
Nov 14 - Nov 21
7 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,664, price is now $2,343 per person
$2,343
per person
found 1 day ago
The condo and property was clean and well decorated and maintained. We had an awesome stay and will return.
Reviewed on Jul 19, 2026
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (1,001 reviews)
Oct 30 - Nov 2
3 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Coach
Philipsburg (SXM) to Boston (BOS)
Southwest Airlines • Coach
Price was $1,027, price is now $680 per person
$680
per person
found 1 day ago
The property was beautiful, clean and the staff was impeccable! They put a bottle of wine in my room on my birthday. The front desk was amazing and also the housekeepers.
Reviewed on Aug 13, 2026
4.5-star property
Panorama Residences at Monte Vista
Point Blanche
9.6/10 Exceptional! (89 reviews)
Oct 30 - Nov 2
3 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Coach
Philipsburg (SXM) to Boston (BOS)
Southwest Airlines • Coach
Price was $1,122, price is now $774 per person
$774
per person
found 1 day ago
The property was well maintained. The room was stunning and the views were spectacular! Ms Nicky referred me to a driver who was prompt and reliable. I would 100% recommend this property to anyone looking to vacay in St Maarten!!
Reviewed on Aug 27, 2026
Top rated hotels for your Lesser Antilles vacation package
The Westin St. Thomas Beach Resort & Spa
5 Estate Bakkeroe St. Thomas St. Thomas
102.07 mi from city center
$336 nightly
The price is $378 total per night
$378 total
Sep 14 - Sep 15
Total with taxes and fees
Guests of The Westin St. Thomas Beach Resort & Spa have access to a full-service spa, 3 outdoor pools, and a gym. Valet parking is USD 40 per day if you plan to drive, or hop aboard the airport shuttle during limited hours for USD 42 per person one-way. The 24-hour front desk has staff standing by to help with concierge services and dry cleaning/laundry. Other amenities at this luxury resort include a sauna, free WiFi in public areas, and meeting rooms.
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
$162 nightly
The price is $170 total per night
$170 total
Sep 13 - Sep 14
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.
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
Free Cancellation
Reserve now, pay when you stay
27.6 mi from city center
$460 nightly
The price is $484 total per night
$484 total
Sep 29 - Sep 30
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 luggage storage, concierge services, and securing valuables. Other amenities at this spa resort include free WiFi in public areas, free newspapers, and a terrace.
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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.
