Sint Maarten Mountain Vacations
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Flight and Mountain hotel deals in Sint Maarten
Price found within the past 48 hours. Click for updated prices.
Coral Beach Club Villas & Marina
Oyster Pond
CA $2,712
per person
Nov 17 - Nov 22
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (119 reviews)
The condo and property was clean and well decorated and maintained. We had an awesome stay and will return.
Reviewed on Jul 19, 2026
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View all trips5* Mountain holidays in Sint Maarten
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View all trips3 Night Mountain holidays in Sint Maarten
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View all trips4 Night Mountain holidays in Sint Maarten
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Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
CA $951
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
The staff is very friendly and accommodating. Beautiful views. The only thing I would ask is that water be restocked daily because it is easy to get dehydrated even if you buy your own water.
Reviewed on Sep 14, 2026
Simpson Bay Resort, Marina & Spa
Pelican Key
CA $1,181
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,987 reviews)
The property is older/dated, however, it is clean. The staff were friendly and helpful.
Reviewed on Sep 15, 2026
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View all tripsMountain Hotels in Sint Maarten
Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
- 27 min walk from Maho Beach
CA $167
CA $212 total
Sep 20 - Sep 21
includes taxes & fees
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,750 reviews)
"This was my 4th time staying at the resort. As always it was fabulous!"
Reviewed on Sep 16, 2026
The Villas at Simpson Bay Resort
Billy Folly Road No. 37A Simpson Bay
- 27 min walk from Maho Beach
CA $237
CA $284 total
Sep 17 - Sep 18
includes taxes & fees
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our ...
9.2/10 Wonderful! (1,534 reviews)
"Great hotel"
Reviewed on Sep 14, 2026
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond Road No 156 Oyster Pond
- 12 min drive from Maho Beach
CA $235
CA $287 total
Oct 16 - Oct 17
includes taxes & fees
Book a stay at this family-friendly hotel in Oyster Pond. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9.2/10 Wonderful! (1,001 reviews)
"The staff is very friendly and accommodating. Beautiful views. The only thing I would ask is that water be restocked daily because it is easy to get dehydrated even if you buy your own water."
Reviewed on Sep 14, 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.
Things to do
High-Speed Ferry to St. Barths
CA $112
per adult
80% of travellers recommend
St Maarten Beach hopping tour (Oreint beach and Maho beach combo)
CA $83
per adult
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
CA $220
per adult
90% 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.
