
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
8.8/10 Excellent! (1,048 reviews)
Jul 11 - Jul 14
3 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
United • Coach
Philipsburg (SXM) to Newark Liberty Intl. Airport (EWR)
American Airlines • Coach
Save 100% on your flight
per person
found 23 hours ago
Very nice property. Our only complaint it that it appears that they add a bleach smell to the air of both the condo unit and the main lobby that was bothersome. Everything else was excellent, including service from bellmen and others.
Reviewed on Mar 22, 2025

4.0-star property
The Villas at Simpson Bay Resort
9.2/10 Wonderful! (1,154 reviews)
Jul 3 - Jul 6
3 night stay
Chicago (CHI) to Philipsburg (SXM)
United • Non-stop roundtrip • Coach
per person
found 1 day ago
Everything you need right at the resort though there are several other restaurants within walking distance. The staff are Coco Beach bar are the best!!
Reviewed on Apr 12, 2025

4.0-star property
Divi Little Bay Beach Resort
8.4/10 Very Good! (1,003 reviews)
Jun 1 - Jun 8
7 night stay
Chicago (CHI) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Chicago (CHI)
Copa • Non-stop • Coach
Save 100% on your flight
per person
found 1 day ago
Nice grounds, well kept and maintained. Beautiful property.
Reviewed on Apr 1, 2025

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
The price is $231 per night
$231
per night
May 4 - May 5
Sonesta Maho Beach All Inclusive Resort Casino & Spa features a full-service spa, a casino, and a free water park. 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 beach property include karaoke, an outdoor pool, and a children's pool.
Pool
Breakfast included

Margaritaville Vacation Club - St. Thomas
6080 Estate Smith Bay, St. Thomas
99.41 mi from city center
The price is $384 per night
$384
per night
May 5 - May 6
Guests staying at Margaritaville Vacation Club - St. Thomas enjoy access to 2 outdoor pools, a gym, and free WiFi in public areas. You can take advantage of free parking, along with a shopping center shuttle. The front desk has multilingual staff standing by 24 hours a day to assist with tours/tickets and luggage storage. Other amenities at this beach hotel include a computer station, a terrace, and laundry facilities.
Pool
Parking included

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
The price is $144 per night
$144
per night
May 15 - May 16
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
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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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