
Sint Maarten Cheap Vacations
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Flight and Cheap 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 $1,643, price is now CA $1,173 per person
CA $1,173
per person
Apr 23 - Apr 27
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
8.6/10 Excellent! (952 reviews)
We were a group of 6 who stayed at the resort and all enjoyed our stay. The staff were all friendly. The rooms were clean and comfortable. We liked that the hotel was in a quieter spot on the island. The pool is gorgeous and we enjoyed the beach too (even with some sargassum).
Reviewed on Feb 18, 2026

Simpson Bay Resort, Marina & Spa
Pelican Key
Price was CA $2,820, price is now CA $1,315 per person
CA $1,315
per person
Mar 22 - Mar 26
just found
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,463 reviews)
Original room view of parking and building on ground floor not great 2nd day switched room for fee, much better. Beaches nice pools nice restaurants great and location to Simpson Bay Area good.
Reviewed on Feb 19, 2026

Divi Little Bay Beach Resort
Price was CA $2,295, price is now CA $1,607 per person
CA $1,607
per person
Apr 23 - Apr 27
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
8.4/10 Very Good! (1,002 reviews)
Understaffed, in need of updates (rooms, property), cockroaches in room. Customer service very poor - long wait for service at restaurants. Wait staff can be rude but are also overwhelmed.
Reviewed on Feb 15, 2026

Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key
Price was CA $1,819, price is now CA $1,391 per person
CA $1,391
per person
Mar 22 - Mar 26
just found
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,339 reviews)
Changing rooms isn’t fun at 7 pm with a family
Reviewed on Feb 20, 2026

Holland House Beach Hotel
Downtown Philipsburg
Price was CA $2,281, price is now CA $1,770 per person
CA $1,770
per person
Mar 22 - Mar 26
just found
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,002 reviews)
The staff was helpful and friendly. Keisha in the restaurant put a smile on my face everyday. The breakfast was incredible. That was a pleasant surprise. The location of the hotel on the beach was great. The front desk staff seemed to be involved in everything! They were all knowledgeable and helpful. We were unsure about staying here, as Philipsburg gets very quiet after the cruise ships leave, but after the stay, we couldn’t be any happier with our choice to stay at the Holland House.
Reviewed on Feb 20, 2026
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View all trips3 Night Cheap holidays in Sint Maarten
Price found within the past 48 hours. Click for updated prices.

Oyster Bay Beach Resort
Oyster Pond
Price was CA $1,081, price is now CA $793 per person
CA $793
per person
May 2 - May 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
8.6/10 Excellent! (952 reviews)
We were a group of 6 who stayed at the resort and all enjoyed our stay. The staff were all friendly. The rooms were clean and comfortable. We liked that the hotel was in a quieter spot on the island. The pool is gorgeous and we enjoyed the beach too (even with some sargassum).
Reviewed on Feb 18, 2026

Simpson Bay Resort, Marina & Spa
Pelican Key
Price was CA $1,831, price is now CA $954 per person
CA $954
per person
May 2 - May 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,463 reviews)
Original room view of parking and building on ground floor not great 2nd day switched room for fee, much better. Beaches nice pools nice restaurants great and location to Simpson Bay Area good.
Reviewed on Feb 19, 2026

Divi Little Bay Beach Resort
Price was CA $1,526, price is now CA $1,084 per person
CA $1,084
per person
May 2 - May 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
8.4/10 Very Good! (1,002 reviews)
Understaffed, in need of updates (rooms, property), cockroaches in room. Customer service very poor - long wait for service at restaurants. Wait staff can be rude but are also overwhelmed.
Reviewed on Feb 15, 2026
Don't see what you're looking for?
See all available trips from Columbus to Sint Maarten
View all trips4 Night Cheap holidays in Sint Maarten
Price found within the past 48 hours. Click for updated prices.

Oyster Bay Beach Resort
Oyster Pond
Price was CA $1,643, price is now CA $1,173 per person
CA $1,173
per person
Apr 23 - Apr 27
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
8.6/10 Excellent! (952 reviews)
We were a group of 6 who stayed at the resort and all enjoyed our stay. The staff were all friendly. The rooms were clean and comfortable. We liked that the hotel was in a quieter spot on the island. The pool is gorgeous and we enjoyed the beach too (even with some sargassum).
Reviewed on Feb 18, 2026

Simpson Bay Resort, Marina & Spa
Pelican Key
Price was CA $2,820, price is now CA $1,315 per person
CA $1,315
per person
Mar 22 - Mar 26
just found
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,463 reviews)
Original room view of parking and building on ground floor not great 2nd day switched room for fee, much better. Beaches nice pools nice restaurants great and location to Simpson Bay Area good.
Reviewed on Feb 19, 2026

Divi Little Bay Beach Resort
Price was CA $2,295, price is now CA $1,607 per person
CA $1,607
per person
Apr 23 - Apr 27
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
8.4/10 Very Good! (1,002 reviews)
Understaffed, in need of updates (rooms, property), cockroaches in room. Customer service very poor - long wait for service at restaurants. Wait staff can be rude but are also overwhelmed.
Reviewed on Feb 15, 2026
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See all available trips from Columbus to Sint Maarten
View all tripsCheap Hotels in Sint Maarten

Vicky's Keys - Hostel
The Keys Road 2-8, Lane 3 Philipsburg
Stay at this hostel in Philipsburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Orient Bay Beach and Maho Beach are located ...
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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