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
The Morgan Resort Spa Village
9/10 Wonderful! (2,412 reviews)
Nov 13 - Nov 16
3 night stay
Boston (BOS) to Philipsburg (SXM)
Air Canada • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
American Airlines • Non-stop • Coach
Price was $1,501, price is now $1,012 per person
$1,012
per person
found 1 day ago
Outstanding
Reviewed on Oct 7, 2026
4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (2,074 reviews)
Jan 1 - Jan 6
5 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Price was $3,301, price is now $1,442 per person
$1,442
per person
found 13 hours ago
Clean spacious room. Lots to do and eat within walking distance.
Reviewed on Oct 9, 2026
4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,560 reviews)
Jan 2 - Jan 6
4 night stay
Boston (BOS) to Philipsburg (SXM)
Southwest Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
American Airlines • Non-stop • Coach
Price was $3,315, price is now $1,605 per person
$1,605
per person
found 1 day ago
Loved it all complimentary bottle of Chilean wine. We had an ocean/pool view one bedroom villa and just loved it. Absolutely loved the staff especially Monique who had amazing dinner recommendations for us at her fingertips. Ask for her! 10/10
Reviewed on Oct 9, 2026
4.5-star property
Panorama Residences at Monte Vista
Point Blanche
9.6/10 Exceptional! (98 reviews)
Dec 10 - Dec 15
5 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Price was $1,781, price is now $1,100 per person
$1,100
per person
found 1 day ago
Amazing stay
Reviewed on Oct 6, 2026
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (1,001 reviews)
Jan 2 - Jan 6
4 night stay
Boston (BOS) to Philipsburg (SXM)
Southwest Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,654, price is now $1,116 per person
$1,116
per person
found 1 day ago
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
$161 nightly
The price is $169 total per night
$169 total
Oct 14 - Oct 15
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, luggage storage, and securing valuables. Other amenities at this beach resort include 6 outdoor pools, a children's pool, and a gym.
On private beach
Pool
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
$423 nightly
The price is $441 total per night
$441 total
Oct 13 - Oct 14
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
Bluebeard's Castle Resort
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
102.67 mi from city center
$203 nightly
The price is $228 total per night
$228 total
Nov 8 - Nov 9
Total with taxes and fees
Guests of Bluebeard's Castle Resort have access to an outdoor pool, a gym, and free WiFi in public areas. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Additional amenities include a hot tub, laundry facilities, and an ATM.
Pool
Hot Tub
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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.
