Simpson Bay Vacation Packages

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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.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $1,582, price is now CA $908 per person
CA $908
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Philipsburg (SXM)
9.2/10 Wonderful! (960 reviews)
Its a beautiful property and the customer service experience is wonderful

Reviewed on Aug. 30, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was CA $2,443, price is now CA $1,090 per person
CA $1,090
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Philipsburg (SXM)
9.2/10 Wonderful! (1,244 reviews)
Great location, great service on the beach. Check in was a long process. The first room assigned was not ideal, close to the noise and with a blocked view, Initial upgrade was also not ideal at lower parking lot level (light sleeper). Third move was the charm.

Reviewed on Sep. 5, 2025

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $2,255, price is now CA $1,025 per person
CA $1,025
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Philipsburg (SXM)
9/10 Wonderful! (1,321 reviews)
Need more service quality

Reviewed on Sep. 4, 2025

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was CA $1,672, price is now CA $941 per person
CA $941
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Philipsburg (SXM)
8.6/10 Excellent! (925 reviews)
The staff was great and the food was delicious!!

Reviewed on Sep. 3, 2025

Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
Price was CA $1,564, price is now CA $917 per person
CA $917
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Philipsburg (SXM)
9/10 Wonderful! (1,106 reviews)
We hung at the bar for the time of our stay and Morgan was exceptional. There was also Marie, Devon and Adriel (I knicknaned him Baby). I had one minor issue with my room it was resolved in a matter of minutes with an email to follow up. This was my second stay as I usually stay at Simpson Bay, but it sure bet will not be that last. See you all in a couple of weeks!

Reviewed on Sep. 5, 2025

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?

 

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Simpson Bay Hotel Deals

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from Sep 25 to Sep 26
CA $114
CA $137 total
Sep 25 - Sep 26
includes taxes & fees
Simpson Bay Resort, Marina & Spa
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road, Simpson Bay
The price is CA $301 per night from Sep 8 to Sep 9
CA $301
CA $399 total
Sep 8 - Sep 9
includes taxes & fees
The Morgan Resort Spa Village
Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

4 out of 5
Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $107 per night from Sep 24 to Sep 25
CA $107
CA $149 total
Sep 24 - Sep 25
includes taxes & fees
Hilton Vacation Club Flamingo Beach St. Maarten
See all 457 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Simpson Bay

Kim Sha Beach

Kim Sha Beach

Why not spend a carefree afternoon at Kim Sha Beach during your travels in Simpson Bay? Check out the shops and top-notch restaurants in this romantic area.

Kim Sha Beach
Hollywood Casino which includes a casino and interior views

Hollywood Casino

Bingo, a handful of gambling tables, buffets and piano bars entertain the public at this almost intimate gambling hall.

Hollywood Casino

What to do in Simpson Bay

Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

CA $205
per adult
82% of travellers recommend
Ultimate Prickly Pear and Anguilla Experience
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

CA $118
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
Pinel Island!!

Best Of Full-Day Snorkeling and Beach Excursion with Hot Lunch in Sint Maarten

CA $191
per adult
100% of travellers recommend
Best Of Full-Day Snorkeling and Beach Excursion with Hot Lunch in Sint Maarten
See all activities in Simpson Bay
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.