
Lesser Antilles Vacation Packages
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4.0-star property
Holland House Beach Hotel
Downtown Philipsburg
9.2/10 Wonderful! (1,000 reviews)
Jan 11 - Jan 15
4 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Delta • Non-stop • Coach
Price was $1,440, price is now $907 per person
$907
per person
found 1 day ago
The staff are amazing and it is super convenient to stores.
Breakfast was great!
Reviewed on Sep 5, 2025

4.0-star property
The Villas at Simpson Bay Resort
9.2/10 Wonderful! (1,268 reviews)
Dec 13 - Dec 18
5 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Delta • Non-stop • Coach
Price was $1,839, price is now $1,020 per person
$1,020
per person
found 1 day ago
Balcony was a beautiful view
Reviewed on Oct 29, 2025

4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (1,398 reviews)
Jan 7 - Jan 12
5 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,052, price is now $1,140 per person
$1,140
per person
found 1 day ago
I had a 7 night stay at this resort when I get there I realize my ac wasn’t working as it should and without the ceiling fan the room wouldn’t cold I report this issues they say they will get it fix nxt day I see it was leaking in the closet area I report it again on the third night I called the front desk n I told them I’m really hot here n it’s not working I didn’t want to move because I had a early trip to Anguilla n would be no til later in the night. I wanted a good night sleep so they offer an additional fan then I change my mind n tel her to move me she found 2 room my husband went and check them out I pack all our stuff n ready to move then I got a called saying no to take everything as they only moving me for the night I was upset n I say at this point I wanna sleep when I get bk I will deal with the moving again I asked y would we have to move again she say because the room was in a different part and was a bigger room I said ok. The following day my husband got a call on his wats app n they apologized for the inconvenience and say they will let us stay in the room they move us to ( upgraded stay) apart from tht the front desk staff n everyone was so warm n friendly i would definitely stay again on my nxt visit to st martin
Reviewed on Oct 30, 2025

4.0-star property
La Playa Orient Bay
9.4/10 Exceptional! (594 reviews)
Dec 16 - Dec 21
5 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,746, price is now $1,164 per person
$1,164
per person
found 1 day ago
All the folks working at this property were great. The resort was nice but not pretentious.
Reviewed on Nov 18, 2024

4.0-star property
Oceans at Divi Little Bay
8.4/10 Very Good! (262 reviews)
Dec 24 - Dec 28
4 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
United • Non-stop • Coach
Price was $3,290, price is now $2,255 per person
$2,255
per person
found 1 day ago
Great property for families
Reviewed on Jul 31, 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
$362 nightly
The price is $378 total per night
$378 total
Nov 17 - Nov 18
Total with taxes and fees
Sonesta Maho Beach All Inclusive Resort Casino & Spa features a full-service spa, 2 outdoor pools, and a casino. Self parking is offered for USD 10 per day. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, luggage storage, and tours or tickets. Other amenities at this all-inclusive property include a free water park, karaoke, and a children's pool.
Pool
All inclusive

The Westin St. Thomas Beach Resort & Spa
5 Estate Bakkeroe, Po Box 7100, St. Thomas, St. Thomas
Free Cancellation
Reserve now, pay when you stay
102.05 mi from city center
$501 nightly
The price is $563 total per night
$563 total
Dec 4 - Dec 5
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 35 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 beach resort include a sauna, free WiFi in public areas, and meeting rooms.
Pool
Spa

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
$119 nightly
The price is $124 total per night
$124 total
Nov 23 - Nov 24
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
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