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.
Oyster Bay Beach Resort
Oyster Pond
Price was CA $1,321, price is now CA $995 per person
CA $995
per person
Jul 13 - Jul 17
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
8.8/10 Excellent! (1,000 reviews)
The FREE happy hour drinks on the patio with live music was unexpected and amazing!
Reviewed on Jun 11, 2026
The Villas at Simpson Bay Resort
Pelican Key
Price was CA $2,472, price is now CA $1,355 per person
CA $1,355
per person
Jul 13 - Jul 17
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,412 reviews)
We loved our stay at the Villas. It was centrally located to great restaurants and markets.
Reviewed on Jun 11, 2026
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was CA $2,198, price is now CA $1,239 per person
CA $1,239
per person
Jul 13 - Jul 17
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,765 reviews)
Many different restaurants in sure the beach was lovely. Staff is so friendly and willing to help.
Reviewed on Jun 12, 2026
Sonesta Ocean Point All Inclusive, Adults Only Resort
Price was CA $4,154, price is now CA $3,044 per person
CA $3,044
per person
Aug 13 - Aug 17
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
8.8/10 Excellent! (1,000 reviews)
The Pools and swim up bar was in good shape and well maintained.
Reviewed on Jun 9, 2026
Divi Little Bay Beach Resort
Price was CA $1,796, price is now CA $1,369 per person
CA $1,369
per person
Aug 13 - Aug 17
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
8.2/10 Very Good! (1,006 reviews)
Easy access to beach. Both pools were great. Had on-site water activities which were very convenient. Parking was free. Property is big so lots of walking which we loved.
Reviewed on Jun 10, 2026
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See all available trips from Columbus to Sint Maarten
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 $4,154, price is now CA $3,044 per person
CA $3,044
per person
Aug 13 - Aug 17
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
8.8/10 Excellent! (1,000 reviews)
The Pools and swim up bar was in good shape and well maintained.
Reviewed on Jun 9, 2026
Don't see what you're looking for?
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.
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was CA $1,726, price is now CA $1,008 per person
CA $1,008
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,765 reviews)
Many different restaurants in sure the beach was lovely. Staff is so friendly and willing to help.
Reviewed on Jun 12, 2026
The Villas at Simpson Bay Resort
Pelican Key
Price was CA $2,166, price is now CA $1,352 per person
CA $1,352
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,412 reviews)
We loved our stay at the Villas. It was centrally located to great restaurants and markets.
Reviewed on Jun 11, 2026
Divi Little Bay Beach Resort
Price was CA $1,506, price is now CA $1,202 per person
CA $1,202
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
8.2/10 Very Good! (1,006 reviews)
Easy access to beach. Both pools were great. Had on-site water activities which were very convenient. Parking was free. Property is big so lots of walking which we loved.
Reviewed on Jun 10, 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.
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Price was CA $1,713, price is now CA $1,110 per person
CA $1,110
per person
Jul 13 - Jul 17
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,003 reviews)
The riom was clean and spacious . Staff were friendly
Reviewed on Jun 11, 2026
The Villas at Simpson Bay Resort
Pelican Key
Price was CA $2,472, price is now CA $1,355 per person
CA $1,355
per person
Jul 13 - Jul 17
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,412 reviews)
We loved our stay at the Villas. It was centrally located to great restaurants and markets.
Reviewed on Jun 11, 2026
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was CA $2,198, price is now CA $1,239 per person
CA $1,239
per person
Jul 13 - Jul 17
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,765 reviews)
Many different restaurants in sure the beach was lovely. Staff is so friendly and willing to help.
Reviewed on Jun 12, 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 $168 per night from Jul 3 to Jul 4
CA $168
CA $213 total
Jul 3 - Jul 4
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! (1,606 reviews)
"The room was very clean, staff very helpful and friendly. They didn’t offer any breakfast and I will recommend it to my family and friends anytime."
Reviewed on Jun 9, 2026
The Villas at Simpson Bay Resort
Billy Folly Road No. 37A Simpson Bay
The price is CA $358 per night from Jun 16 to Jun 17
CA $358
CA $439 total
Jun 16 - Jun 17
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! (1,431 reviews)
"We loved our stay at the Villas. It was centrally located to great restaurants and markets."
Reviewed on Jun 11, 2026
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond Road No 156 Oyster Pond
The price is CA $204 per night from Jun 15 to Jun 16
CA $204
CA $245 total
Jun 15 - Jun 16
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! (1,007 reviews)
"The riom was clean and spacious . Staff were friendly"
Reviewed on Jun 11, 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.
