Simpson Bay Vacation Packages
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Your Simpson Bay Vacation
With a vacation package to Simpson Bay, all the organizing is done beforehand. This gives you a lot more time to discover some of the features that define this beachfront city, such as its lively atmosphere, beaches and cosmopolitan vibe. If sightseeing is on the to-do list during your trip to Simpson Bay, check out leading attractions like Maho Beach, Marigot Market and Fort St. Louis. Don't delay visiting this destination any longer. Your dream Simpson Bay vacation is a couple of clicks away with Expedia.
Top Simpson Bay Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was CA $2,802, price is now CA $1,643 per person
CA $1,643
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,765 reviews)
Great pools. Great beach. Great restaurants.
Reviewed on Jun 8, 2026
The Villas at Simpson Bay Resort
Pelican Key
Price was CA $3,337, price is now CA $1,839 per person
CA $1,839
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,412 reviews)
We stayed at this resort in mid May 2026. The resort is beautiful with gorgeous views and waterfront rooms. We loved our balcony and we pretty much loved everything about our room. Lovely resort at a great price. Excellent location, would definitely stay here again.
Reviewed on Jun 9, 2026
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Price was CA $3,359, price is now CA $2,273 per person
CA $2,273
per person
Jul 18 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,003 reviews)
Staff was very friendly and helpful. Definitely would suggest renting a car if staying here.
Reviewed on Jun 10, 2026
Sonesta Ocean Point All Inclusive, Adults Only Resort
Price was CA $3,722, price is now CA $2,753 per person
CA $2,753
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,000 reviews)
The Pools and swim up bar was in good shape and well maintained.
Reviewed on Jun 9, 2026
La Playa Orient Bay
Price was CA $2,287, price is now CA $1,700 per person
CA $1,700
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.4/10 Exceptional! (725 reviews)
Excelente ubicación, playa, a 50 metros de la plaza de negocios y restaurantes. Espectacular desayuno frente al mar
Reviewed on Jun 8, 2026
Simpson Bay Beach Vacation
There's nothing like a Simpson Bay vacation to put a spring in your step. The soothing sound of rolling surf and the smell of salty sea air are sure to rejuvenate your mind and body. To be close to the city centre on your trip to Simpson Bay, find a hotel around Simpson Bay Beach (just 2 kilometres away). If you're planning to stay for a while, take a peek at our Simpson Bay vacation deals. Not only will you be able to save cash, you'll also have other amazing beaches near you to explore, like Kim Sha Beach and Lay Bay Beach.
Things You Should Know About Simpson Bay
- Why not think about Simpson Bay beach hotels for your next vacation? See what's available — there's nothing like staying at just minutes from the water.
- If your idea of an amazing beach vacation involves staying in one of our villas, Cocovaa or The Morgan Resort & Spa will suit you perfectly.
Simpson Bay Hotel Deals
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $330 per night from Jun 25 to Jun 26
CA $330
CA $432 total
Jun 25 - Jun 26
includes taxes & fees
9/10 Wonderful! (2,217 reviews)
"The hotel was beautiful with a great infinity pool. Staff at the pool were great and very accommodating."
Reviewed on Jun 9, 2026
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $296 per night from Jun 15 to Jun 16
CA $296
CA $362 total
Jun 15 - Jun 16
includes taxes & fees
9/10 Wonderful! (1,779 reviews)
"Great pools. Great beach. Great restaurants."
Reviewed on Jun 8, 2026
Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Jun 24 to Jun 25
CA $171
CA $216 total
Jun 24 - Jun 25
includes taxes & fees
9.2/10 Wonderful! (1,605 reviews)
"The room was very clean, staff very helpful and friendly. They didn’t offer any breakfast and I will recommend it to my family and friends anytime."
Reviewed on Jun 9, 2026
Lowest 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.
Discover the most popular places to visit in Simpson Bay
Kim Sha Beach
4/5(17 reviews)
Why not spend a carefree afternoon at Kim Sha Beach during your travels in Simpson Bay? Check out the shops and top-notch restaurants in this romantic area.
Hollywood Casino
Bingo, a handful of gambling tables, buffets and piano bars entertain the public at this almost intimate gambling hall.
What to do in Simpson Bay
Half Day Snorkeling Adventure
CA $90
per adult
100% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
CA $118
per adult
94% of travellers recommend
High-Speed Ferry to St. Barths
CA $103
per adult
80% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
