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.
The Villas at Simpson Bay Resort
Pelican Key
Price was CA $2,199, price is now CA $900 per person
CA $900
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,386 reviews)
Property and hotel grounds, pool and beach front were beautiful. Rooms were clean but basic. Only one ice machine in each building. Staff very friendly, helpful and accommodating.
Reviewed on Apr 28, 2026
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was CA $3,330, price is now CA $1,309 per person
CA $1,309
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,665 reviews)
Great location close to restaurants, stores and night life
Reviewed on May 1, 2026
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Price was CA $3,961, price is now CA $2,492 per person
CA $2,492
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,001 reviews)
Great Stay, Property was super clean and nice. Staff was friendly, informative, & super helpful !! I will be back !
Reviewed on Apr 30, 2026
Panorama Residences at Monte Vista
Point Blanche
Price was CA $1,709, price is now CA $1,135 per person
CA $1,135
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.6/10 Exceptional! (51 reviews)
My stay in Sint Maarten was nothing short of amazing. The apartment was clean, spacious, and beautifully maintained, making it feel like a home away from home. From the moment I arrived, everything was set up perfectly, and the attention to detail really stood out.
The location was ideal—close to the beach, restaurants, and local attractions, yet still peaceful enough to relax and unwind. Waking up to the island breeze and scenic views every day was a highlight of the trip.
The amenities were exactly as described, and everything worked smoothly. Whether it was lounging inside or stepping out to explore, the apartment provided the perfect balance of comfort and convenience.
Overall, this was a great experience, and I would definitely stay here again. I highly recommend it to anyone looking for a relaxing and enjoyable stay in Sint Maarten.
Reviewed on Apr 22, 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 $419 per night from May 4 to May 5
CA $419
CA $531 total
May 4 - May 5
includes taxes & fees
9/10 Wonderful! (2,107 reviews)
The bell men that helped park the cars were so friendly! Like literally awesome. Every single woman that was at the front desk were very rude….
Reviewed on Apr 30, 2026
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
The price is CA $299 per night from May 17 to May 18
CA $299
CA $368 total
May 17 - May 18
includes taxes & fees
9/10 Wonderful! (1,682 reviews)
Great location close to restaurants, stores and night life
Reviewed on May 1, 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 $160 per night from May 18 to May 19
CA $160
CA $204 total
May 18 - May 19
includes taxes & fees
9.2/10 Wonderful! (1,536 reviews)
Property, room and beach are nice. Difficult to get daily change of Bathroom and beach towels due to limited room service.
Reviewed on Apr 30, 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 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.
