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! (2,074 reviews)
Jan 13 - Jan 18
5 night stay
New York (JFK) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Price was $2,590, price is now $1,274 per person
$1,274
per person
found 23 hours ago
Great property! Had a good solo trip/birthday vacay staying here. It is walkable to a lot of nearby restaurants and beaches (with one right on the resort)! The staff were friendly and they have a shuttle that can take you around the resort seeing that it is a big property; they even have several pools at this resort (though one of their biggest one was shut down for maintenance) It was very clean and in the mornings I would see some workers cleaning off my patio from things that just blew around overnight - Thank you!! Would recommend to anyone.
Reviewed on Oct 19, 2026
4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,560 reviews)
Jan 4 - Jan 8
4 night stay
Hartford (BDL) to Philipsburg (SXM)
Southwest Airlines • Non-stop roundtrip • Coach
Price was $3,057, price is now $1,476 per person
$1,476
per person
found 21 hours ago
Will be be back
Reviewed on Oct 17, 2026
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (1,001 reviews)
Dec 30 - Jan 4
5 night stay
Hartford (BDL) to Philipsburg (SXM)
United • Non-stop • Coach
Philipsburg (SXM) to Hartford (BDL)
American Airlines • Non-stop • Coach
Price was $2,695, price is now $1,548 per person
$1,548
per person
found 1 day ago
4.0-star property
Oyster Bay Beach Resort
Oyster Pond
9/10 Wonderful! (1,006 reviews)
Dec 30 - Jan 4
5 night stay
Hartford (BDL) to Philipsburg (SXM)
United • Non-stop • Coach
Philipsburg (SXM) to Hartford (BDL)
American Airlines • Non-stop • Coach
Price was $1,828, price is now $1,299 per person
$1,299
per person
found 1 day ago
My stay was great…..Staff was amazing super accommodating! I couldn’t have picked a better resort
Reviewed on Oct 19, 2026
4.0-star property
Divi Little Bay Beach Resort
8.2/10 Very Good! (1,010 reviews)
Dec 30 - Jan 4
5 night stay
Hartford (BDL) to Philipsburg (SXM)
United • Non-stop • Coach
Philipsburg (SXM) to Hartford (BDL)
American Airlines • Non-stop • Coach
Price was $2,956, price is now $2,125 per person
$2,125
per person
found 1 day ago
Room was so spacious! I appreciated the little kitchenette in the room!
Reviewed on Oct 19, 2026
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
$198 nightly
The price is $207 total per night
$207 total
Oct 21 - Oct 22
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 securing valuables, luggage storage, and concierge services. 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
$465 nightly
The price is $488 total per night
$488 total
Nov 19 - Nov 20
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 18 - Nov 19
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.
