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.
Oyster Bay Beach Resort
Oyster Pond
Price was CA $1,735, price is now CA $1,058 per person
CA $1,058
per person
May 28 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
8.6/10 Excellent! (1,006 reviews)
The hotel is isolated with 2 restaurant options, both great. Pool is beautiful, beach unfortunately full off seaweed and unusable to no fault of the resorts. Car is a must if you want to see the island. Overall we were very happy with resort and would return.
Reviewed on Apr 13, 2026
The Villas at Simpson Bay Resort
Pelican Key
Price was CA $4,781, price is now CA $1,845 per person
CA $1,845
per person
May 28 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,382 reviews)
Comfortable stay the view could not have been better.
Reviewed on Apr 13, 2026
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was CA $3,092, price is now CA $1,461 per person
CA $1,461
per person
Jun 28 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,635 reviews)
Clean room, some staff were excellent, others were rude. Resort restaurants were great and convenient.
Reviewed on Apr 17, 2026
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Price was CA $2,210, price is now CA $1,198 per person
CA $1,198
per person
May 28 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,002 reviews)
Staff were really great and helpful!
Reviewed on Apr 16, 2026
The Morgan Resort Spa Village
Price was CA $3,118, price is now CA $1,767 per person
CA $1,767
per person
May 28 - Jun 4
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9/10 Wonderful! (2,052 reviews)
I had partial view of beach, pool was great, pool bar was good.
Reviewed on Apr 14, 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 $380 per night from Apr 19 to Apr 20
CA $380
CA $487 total
Apr 19 - Apr 20
includes taxes & fees
9/10 Wonderful! (2,073 reviews)
Amazing Stay
Reviewed on Apr 15, 2026
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
The price is CA $296 per night from May 14 to May 15
CA $296
CA $361 total
May 14 - May 15
includes taxes & fees
8.8/10 Excellent! (1,659 reviews)
Clean room, some staff were excellent, others were rude. Resort restaurants were great and convenient.
Reviewed on Apr 17, 2026
Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
The price is CA $184 per night from May 18 to May 19
CA $184
CA $229 total
May 18 - May 19
includes taxes & fees
9.2/10 Wonderful! (1,501 reviews)
The Hilton Flamingo was even better than we expected. Staff was very friendly, property was clean and well cared for. Would definitely recommend and hope we can return one day.
Reviewed on Apr 17, 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 $89
per adult
100% of travellers recommend
Underwater Sculpture Park Snorkel Adventure
CA $62
per adult
80% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
CA $116
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.
