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.
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Price was CA $2,001, price is now CA $1,114 per person
CA $1,114
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (973 reviews)
Room was very clean and staff was friendly. The room was spacious and elegant and had a great view.
Reviewed on Feb 5, 2026
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was CA $3,196, price is now CA $1,403 per person
CA $1,403
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9/10 Wonderful! (1,463 reviews)
Clean spacious room. Great housekeeping. Great shuttle service and shuttle staff. Everything you need right on the property. Grounds well maintained. Excellent overall.
Reviewed on Feb 7, 2026
The Villas at Simpson Bay Resort
Pelican Key
Price was CA $4,477, price is now CA $2,251 per person
CA $2,251
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,309 reviews)
It was our 2nd time there. It was great. We love being able to walk to restaurants and live music. Staff is always friendly and funny!
Reviewed on Feb 6, 2026
Oceans at Divi Little Bay
Price was CA $3,264, price is now CA $2,046 per person
CA $2,046
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
8.4/10 Very Good! (266 reviews)
First time ever at Sint Maarten. Our 4-night stay was very enjoyable. The resort staff were very friendly and helpful. Mousekeeping and maintenance staff were very attentive. All facilities were kept clean and in good repair. Very relaxing campus. The food served at all the resort's restaurants was excellent. We especially enjoyed the pizza at "Slice" and the fish & shrimp tacos at "The Shack" were delicious as well. Lovely dinner served on hot lava rocks at "Seabreeze". Great taxi service to rest of island & to/from airport. We will definitely be returning to this resort. Highly recommended!
Reviewed on Feb 7, 2026
Divi Little Bay Beach Resort
Price was CA $3,034, price is now CA $1,920 per person
CA $1,920
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
8.4/10 Very Good! (1,002 reviews)
Beautiful location and views. Pools and beach very nice. Quiet and relaxing. Rooms were clean and adequate. Rooftop restaurant bar and tapas was very nice and really liked the Shack for lunch! The little (not so little) grocery on site was great and so many options of wine and alcohol plus snacks and other drinks. If staying a short time this is fine as I hear prices are a bit higher than outside the resort although to me still reasonable. Need to take cabs or rent a car for anything off the resort recommend renting a car driving is pretty easy and definitely explore! Food on the island is very good.
Reviewed on Feb 5, 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 $555 per night from Feb 15 to Feb 16
CA $555
CA $683 total
Feb 15 - Feb 16
includes taxes & fees
8.8/10 Excellent! (1,991 reviews)
I love the view from the room, although it could have been cleaner in the bathroom. The staff was friendly. Much smaller resort than what I'm used to staying at but it is nice. THERE IS NO DIRECT BEACH ACCESS. For the price I did not expect that. You must walk around to Maho beach to touch sand. ...
Reviewed on Feb 6, 2026
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
The price is CA $419 per night from Feb 15 to Feb 16
CA $419
CA $503 total
Feb 15 - Feb 16
includes taxes & fees
8.8/10 Excellent! (1,593 reviews)
Room was spacious and spotless. Staff was friendly and helpful. The pools were perfect!
Reviewed on Feb 6, 2026
Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
The price is CA $436 per night from Mar 8 to Mar 9
CA $436
CA $494 total
Mar 8 - Mar 9
includes taxes & fees
9/10 Wonderful! (1,429 reviews)
Everything was great would definitely go back
Reviewed on Feb 5, 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 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
High-Speed Ferry to St. Barths
CA $102
per adult
80% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
CA $184
per adult
90% of travellers recommend
Edge Ferry Tickets to St. Barts
CA $136
per adult
84% 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.
