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.
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was CA $1,981, price is now CA $880 per person
CA $880
per person
Jun 14 - Jun 18
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
8.8/10 Excellent! (1,665 reviews)
Very walkable location and grocery store within the resort is very convenient. Excursion available right from the resort docks. Restaurants on site were very good. Breakfast buffest was plentiful. Very family friendly.
Reviewed on Apr 27, 2026
The Villas at Simpson Bay Resort
Pelican Key
Price was CA $3,189, price is now CA $1,569 per person
CA $1,569
per person
May 28 - Jun 1
found 1 hour 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
Coral Beach Club Villas & Marina
Oyster Pond
Price was CA $5,338, price is now CA $3,921 per person
CA $3,921
per person
Jun 28 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9.2/10 Wonderful! (113 reviews)
The Villa was incredible! With a hot tub with ocean view! The staff just perfect
Reviewed on Jan 1, 2026
Oyster Bay Beach Resort
Oyster Pond
Price was CA $3,290, price is now CA $2,445 per person
CA $2,445
per person
Jun 28 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
8.6/10 Excellent! (1,010 reviews)
Super friendly super nice you called them for anything they come immediately the food was great and fantastic. The rental car on the property is cheap. Everything was reasonable I really enjoyed myself
Reviewed on Apr 27, 2026
Divi Little Bay Beach Resort
Price was CA $1,656, price is now CA $1,273 per person
CA $1,273
per person
May 28 - Jun 1
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.2/10 Very Good! (1,012 reviews)
Staff was very unfriendly. NO service at all and waiters were pretending most of the time that they didn't hear you every time you were asking for smth.....like utensils that were not on the table most of the time. Very disorganized when it comes to the restaurants all over the resort.
Reviewed on Apr 26, 2026
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View all trips5* Mountain holidays in Sint Maarten
Price found within the past 48 hours. Click for updated prices.
Sonesta Ocean Point All Inclusive, Adults Only Resort
Price was CA $4,079, price is now CA $4,079 per person
CA $4,079
per person
Jun 29 - Jul 5
found 4 hours ago
Roundtrip flight included
Thunder Bay (YQT) to Philipsburg (SXM)
8.6/10 Excellent! (1,003 reviews)
I loved there. Thanks
Reviewed on Apr 27, 2026
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See all available trips from Columbus to Sint Maarten
View all trips3 Night Mountain holidays in Sint Maarten
Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort
Oyster Pond
Price was CA $941, price is now CA $720 per person
CA $720
per person
Jun 11 - Jun 14
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
8.6/10 Excellent! (1,010 reviews)
Super friendly super nice you called them for anything they come immediately the food was great and fantastic. The rental car on the property is cheap. Everything was reasonable I really enjoyed myself
Reviewed on Apr 27, 2026
The Villas at Simpson Bay Resort
Pelican Key
Price was CA $1,738, price is now CA $868 per person
CA $868
per person
Jul 9 - Jul 12
found 8 hours ago
Roundtrip flight included
Toronto (YTO) 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
Divi Little Bay Beach Resort
Price was CA $1,169, price is now CA $882 per person
CA $882
per person
Jul 9 - Jul 12
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
8.2/10 Very Good! (1,012 reviews)
Staff was very unfriendly. NO service at all and waiters were pretending most of the time that they didn't hear you every time you were asking for smth.....like utensils that were not on the table most of the time. Very disorganized when it comes to the restaurants all over the resort.
Reviewed on Apr 26, 2026
Don't see what you're looking for?
See all available trips from Columbus to Sint Maarten
View all trips4 Night Mountain holidays in Sint Maarten
Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was CA $1,981, price is now CA $880 per person
CA $880
per person
Jun 14 - Jun 18
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
8.8/10 Excellent! (1,665 reviews)
Very walkable location and grocery store within the resort is very convenient. Excursion available right from the resort docks. Restaurants on site were very good. Breakfast buffest was plentiful. Very family friendly.
Reviewed on Apr 27, 2026
The Villas at Simpson Bay Resort
Pelican Key
Price was CA $3,189, price is now CA $1,569 per person
CA $1,569
per person
May 28 - Jun 1
found 1 hour 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
Oyster Bay Beach Resort
Oyster Pond
Price was CA $1,339, price is now CA $998 per person
CA $998
per person
May 28 - Jun 1
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.6/10 Excellent! (1,010 reviews)
Super friendly super nice you called them for anything they come immediately the food was great and fantastic. The rental car on the property is cheap. Everything was reasonable I really enjoyed myself
Reviewed on Apr 27, 2026
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See all available trips from Columbus to Sint Maarten
View all tripsMountain Hotels in Sint Maarten
Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
The price is CA $167 per night from May 18 to May 19
CA $167
CA $211 total
May 18 - May 19
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! (1,528 reviews)
Room was nice,front desk staff was great and very helpful only issue was the staff at pelicans beach bar on the property they are very rude an all seems as if they don’t want to be there 😴 other then that my stay was amazing I will be back .
Reviewed on Apr 27, 2026
The Villas at Simpson Bay Resort
Billy Folly Road No. 37A Simpson Bay
The price is CA $346 per night from May 18 to May 19
CA $346
CA $423 total
May 18 - May 19
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! (1,385 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
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond Road No 156 Oyster Pond
The price is CA $244 per night from May 27 to May 28
CA $244
CA $293 total
May 27 - May 28
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! (1,004 reviews)
We LOVE the rooms at Princess Heights. The view is amazing. Cooking in our room is ideal. The pool is lovely and clean. We’ve been several times and will return!
Reviewed on Apr 26, 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.
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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.
