Sint Maarten Adventure Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Flight and Adventure hotel deals in Sint Maarten

Price found within the past 48 hours. Click for updated prices.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
CA $1,173
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
Beautiful property. Staff very pleasant. Check in was great.

Reviewed on Aug 14, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
CA $1,225
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Newcastle (NEV) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
I had a lovely stay

Reviewed on Aug 14, 2026

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

CA $2,244
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Newcastle (NEV) to Philipsburg (SXM)
8/10 Very good! (3,112 reviews)
Great Resort. Lots of things for kids. Too strict on the teen section for kids around 10-12. Restaurants all nice and accessible. No pre-bookings like other all-inclusives. Great pool service.Nice beach. Check out could be later than 11am.

Reviewed on Aug 14, 2026

Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

Oyster Pond
CA $1,638
per person
Oct 15 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) 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

Holland House Beach Hotel

Holland House Beach Hotel

Downtown Philipsburg
CA $1,241
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,006 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Sint Maarten
View all trips

3 Night Adventure holidays in Sint Maarten

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
CA $776
per person
Oct 22 - Oct 25
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
I had a lovely stay

Reviewed on Aug 14, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
CA $860
per person
Oct 22 - Oct 25
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
Beautiful property. Staff very pleasant. Check in was great.

Reviewed on Aug 14, 2026

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

CA $1,216
per person
Oct 28 - Oct 31
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
8.2/10 Very good! (1,017 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Sint Maarten
View all trips

4 Night Adventure holidays in Sint Maarten

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
CA $1,005
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
I had a lovely stay

Reviewed on Aug 14, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
CA $1,173
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
Beautiful property. Staff very pleasant. Check in was great.

Reviewed on Aug 14, 2026

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond
CA $1,136
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,003 reviews)
The property was beautiful, clean and the staff was impeccable! They put a bottle of wine in my room on my birthday. The front desk was amazing and also the housekeepers.

Reviewed on Aug 13, 2026

Don't see what you're looking for?
See all available trips from Columbus to Sint Maarten
View all trips

Adventure Hotels in Sint Maarten

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

Little Bay Road Philipsburg
  • 8 min drive from Maho Beach
CA $226
CA $298 total
Sep 12 - Sep 13
includes taxes & fees
Book a stay at this beach resort in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff and the clean rooms ...
Divi Little Bay Beach Resort
Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
  • 27 min walk from Maho Beach
CA $153
CA $197 total
Sep 1 - Sep 2
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. ...
Hilton Vacation Club Flamingo Beach St. Maarten
Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

115 Welfare Road Simpson Bay
  • 25 min walk from Maho Beach
CA $188
CA $234 total
Aug 25 - Aug 26
includes taxes & fees
Book a stay at this beach aparthotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ...
Hilton Vacation Club Royal Palm St. Maarten
See all 1,667 properties in Sint Maarten
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

High-Speed Ferry to St. Barths

CA $114
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
Colorful Species Of Birds

Colorful Species Of Birds

CA $69
per adult
94% of travellers recommend
Colorful Species Of Birds
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

CA $190
per adult
90% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
See all activities in Sint Maarten

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.