Simpson Bay Vacation Packages & Trips 2026 from CA $1,193

Your Simpson Bay Vacation

With a vacation package to Simpson Bay, all the organizing is done beforehand. This gives you a lot more time to discover some of the features that define this beachfront city, such as its lively atmosphere, beaches and cosmopolitan vibe. If sightseeing is on the to-do list during your trip to Simpson Bay, check out leading attractions like Maho Beach, Marigot Market and Fort St. Louis. Don't delay visiting this destination any longer. Your dream Simpson Bay vacation is a couple of clicks away with Expedia.

Top Simpson Bay Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Oyster Bay Beach Resort

Oyster Pond

CA $1,193

per person

May 21 - May 28

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

8.6/10 Excellent! (1,021 reviews)

I really enjoyed my stay. Everyone was very friendly and helpful

Reviewed on Mar 28, 2026

The Villas at Simpson Bay Resort

Pelican Key

CA $1,913

per person

May 21 - May 28

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

9.2/10 Wonderful! (1,387 reviews)

Beautiful, well maintained property with great location and amenities. Staff were friendly but seemed to lack training. However, rooms have no soundproofing with screaming kids, squealing chair legs across the tile floors, people pounding on doors and karaoke/reggae music playing all day and all night with rock hard mattresses that were so uncomfortable I got very little sleep and woke up in pain everyday

Reviewed on Mar 29, 2026

Simpson Bay Resort, Marina & Spa

Pelican Key

CA $1,380

per person

Jun 18 - Jun 24

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

9/10 Wonderful! (1,629 reviews)

Wasn't bad... no complaints but I've stayed at better resorts in sint maarten

Reviewed on Mar 31, 2026

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

CA $1,439

per person

May 21 - May 28

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

9.2/10 Wonderful! (1,007 reviews)

We have had another wonderful stay at Princess Heights Luxury Hotel. We were there for 12 days and we love the location. We had the ocean view to wake up to every morning which was amazing and lovely to sit on the patio to wake up slowly. Very quiet location, attentive staff, good restaurants within driving distance. Dawn Beach is close to walk to but small. We were lucky to see some monkeys while there also. We highly recommend this location, however, you do need a car or use a taxi to get around. The pool was lovely and such a great way to relax at the end of a busy day of sightseeing.

Reviewed on Mar 26, 2026

Panorama Residences at Monte Vista

Point Blanche

CA $1,548

per person

May 21 - May 28

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

9.6/10 Exceptional! (29 reviews)

The property is amazing and true to the pictures. Check in was seamless. The only issue we had was our key fob didn’t work one night and we was lock outside out unit until the property manager arrived which took quite some time.

Reviewed on Mar 27, 2026

Simpson Bay Beach Vacation

There's nothing like a Simpson Bay vacation to put a spring in your step. The soothing sound of rolling surf and the smell of salty sea air are sure to rejuvenate your mind and body. To be close to the city centre on your trip to Simpson Bay, find a hotel around Simpson Bay Beach (just 2 kilometres away). If you're planning to stay for a while, take a peek at our Simpson Bay vacation deals. Not only will you be able to save cash, you'll also have other amazing beaches near you to explore, like Kim Sha Beach and Lay Bay Beach.

Things You Should Know About Simpson Bay

Why not think about Simpson Bay beach hotels for your next vacation? See what's available — there's nothing like staying at just minutes from the water.
If your idea of an amazing beach vacation involves staying in one of our villas, Cocovaa or The Morgan Resort & Spa will suit you perfectly.

Ready to book your vacation to Simpson Bay?

Choose your dates

Simpson Bay Hotel Deals

The Morgan Resort Spa Village

2 Beacon Hill Road Simpson Bay

CA $535

CA $662 total

May 1 - May 2

includes taxes & fees

9/10 Wonderful! (2,043 reviews)

The staff, location, property everything was perfect

Reviewed on Mar 31, 2026

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37 Simpson Bay

CA $351

CA $431 total

Apr 21 - Apr 22

includes taxes & fees

8.8/10 Excellent! (1,635 reviews)

N/a

Reviewed on Mar 31, 2026

The Villas at Simpson Bay Resort

Billy Folly Road No. 37A Simpson Bay

CA $403

CA $501 total

May 2 - May 3

includes taxes & fees

9.2/10 Wonderful! (1,383 reviews)

Great stay.

Reviewed on Mar 31, 2026

See all 450 properties in Simpson Bay

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.