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 $2,023, price is now CA $873 per person
CA $873
per person
Jun 18 - Jun 22
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,653 reviews)
Clean room and everyone was very helpful and friendly
Reviewed on Apr 26, 2026
The Villas at Simpson Bay Resort
Pelican Key
Price was CA $3,816, price is now CA $1,581 per person
CA $1,581
per person
Jun 18 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,386 reviews)
Love staying here. We have been staying here for the last 6 years or so. The one complaint we have is the Sewage smell. We stayed in the more North rooms and the smell on the deck was at times to much to sit out there. We have noticed it in the past but this year we worse than normal.
Reviewed on Apr 26, 2026
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Price was CA $2,729, price is now CA $1,463 per person
CA $1,463
per person
Jun 18 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,009 reviews)
Keep up your awesome work Team Princess Heights!
Your friends,
Anvar & Svetlana
Reviewed on Apr 23, 2026
La Playa Orient Bay
Price was CA $2,733, price is now CA $1,635 per person
CA $1,635
per person
Jun 18 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.4/10 Exceptional! (682 reviews)
The things we most like about La Playa are the staff, the director access to the beach with chairs and umbrella provided, a great breakfast provided free of charge every morning including eggs, bacon, bread, fresh fruit, fruit juices, and coffee, and the room. Great place to stay. We book there every year.
Reviewed on Apr 25, 2026
The Morgan Resort Spa Village
Price was CA $2,683, price is now CA $1,649 per person
CA $1,649
per person
Jun 18 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (2,076 reviews)
Second time visiting, I love it here. It’s fantastic. Beds are wonderful clean room very classy.
Reviewed on Apr 24, 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 $410 per night from May 3 to May 4
CA $410
CA $521 total
May 3 - May 4
includes taxes & fees
9/10 Wonderful! (2,103 reviews)
Resort is beautiful. Had the deluxe suite. Beautiful views. Staff super friendly. Only downside , no direct access to a beach. Had to walk a little to maho beach but a longer walk to mullet bay beach is definitely worth the walk. Would certainly stay again.
Reviewed on Apr 25, 2026
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
The price is CA $295 per night from May 14 to May 15
CA $295
CA $360 total
May 14 - May 15
includes taxes & fees
9/10 Wonderful! (1,676 reviews)
Clean room and everyone was very helpful and friendly
Reviewed on Apr 26, 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 $163 per night from May 18 to May 19
CA $163
CA $207 total
May 18 - May 19
includes taxes & fees
9.2/10 Wonderful! (1,526 reviews)
Beach was beautiful
Reviewed on Apr 25, 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
Why not spend a carefree afternoon at Kim Sha Beach during your travels in Simpson Bay? Check out the shops and lively bars 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
Underwater Sculpture Park Snorkel Adventure
CA $62
per adult
Tango Sunset Cruise with Caribbean Dinner & Open Bar
CA $117
per adult
94% 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.
