
Lesser Antilles Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Lesser Antilles vacation package deals
Price found within the past 48 hours. Click for updated prices.

4.0-star property
Oyster Bay Beach Resort
Oyster Pond
9/10 Wonderful! (1,006 reviews)
Dec 9 - Dec 13
4 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Southwest Airlines • Non-stop • Coach
Price was $920, price is now $648 per person
$648
per person
found 1 day ago
the property is secluded, very clean and the staff so helpful and kind. Very beautiful people all around. The hotel room very clean, it was not what I was expecting as far as a hotel room, it was an apartment. Bathroom with double sink, so you have space for that significant other. A nice king size bed waking up to a view, a wrap around balcony from the bedroom to the living room. Kitchen and dinning room to to fill all your personal needs. A home away from home, you feel you belong here, you even have a dishwasher and laundry machine. What else do you need? The grounds have a beautiful infinity pool, laundry mat, gift shop, a market store on the property, spa and gym. Two great restaurants. The only down part was the beach with the frequent storms have been washing up some seaweed waste covering the beach but its just a phase mother nature. There is so many places to go and do. Or you can stay at the resort and be pampered. The staff really go out of their way to take care of their guests. I will miss my favorite Bartender Jeffery and his colorful tasty cocktails. Thank you.
Reviewed on Oct 5, 2026

4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (2,074 reviews)
Dec 12 - Dec 19
7 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Delta • Non-stop • Coach
Price was $2,529, price is now $1,284 per person
$1,284
per person
found 1 day ago
The rooms are clean, the staff is very professional, the beach is clean.
Reviewed on Oct 8, 2026

4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,560 reviews)
Dec 9 - Dec 13
4 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,559, price is now $833 per person
$833
per person
found 1 day ago

3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (1,001 reviews)
Dec 9 - Dec 13
4 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,107, price is now $696 per person
$696
per person
found 1 day ago

3.0-star property
Belair Beach Hotel
Belair
8.8/10 Excellent! (220 reviews)
Dec 9 - Dec 13
4 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Southwest Airlines • Non-stop • Coach
Price was $1,179, price is now $835 per person
$835
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
$481 nightly
The price is $501 total per night
$501 total
Oct 12 - Oct 13
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 7 - Nov 8
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
Don't see what you're looking for?
See all available properties in Lesser Antilles
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.








