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.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
per person
Sep 13 - Sep 20
found 8 hours ago
Roundtrip flight included
Hamilton (YHM) to Philipsburg (SXM)
8.8/10 Excellent! (1,162 reviews)
Helpful staff, great location near food, cute beach

Reviewed on Jul. 5, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 20
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,188 reviews)
Very nice resort conveniently located. Beautiful beach and nice pools. Lots within easy walking distance. Clean, comfortable rooms.

Reviewed on Jul. 2, 2025

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Save 100% on your flight
per person
Sep 13 - Sep 20
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
8.6/10 Excellent! (885 reviews)
This property was beautiful, and the employees were very pleasant and helpful. The grounds were very clean and it is very obvious that everyday they are cleaning up and making improvement to this beach resort.

Reviewed on Jul. 1, 2025

Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 20
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9/10 Wonderful! (1,041 reviews)
Very nice hotel and very friendly staff. Close to the best restaurants in town. Recommended 100 % percent

Reviewed on Jul. 4, 2025

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Save 100% on your flight
per person
Sep 13 - Sep 20
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,001 reviews)
Great customer service from everyone we came in contact with.

Reviewed on Jun. 25, 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?

 

Choose your dates

Simpson Bay Hotel Deals

The Morgan Resort Spa Village
The Morgan Resort Spa Village
4 out of 5
2 Beacon Hill Road, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $279 per night from Jul 13 to Jul 14
CA $279
CA $373 total
Jul 13 - Jul 14
includes taxes & fees
8.8/10 Excellent! (1,729 reviews)
Review
"The bartender Alex and Marteen were excellent hosts. The front desk was very rude and unaccomadating. I had to wait over 3 hours to check in while watching other guests get their room right away. Also Ravi who drove the airport shuttle was a very nice gentleman."

Reviewed on Jul. 4, 2025

The Morgan Resort Spa Village
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 $116 per night from Aug 5 to Aug 6
CA $116
CA $140 total
Aug 5 - Aug 6
includes taxes & fees
8.8/10 Excellent! (1,184 reviews)
"Nice vacation"

Reviewed on Jul. 3, 2025

Simpson Bay Resort, Marina & Spa
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 $187 per night from Jul 29 to Jul 30
CA $187
CA $232 total
Jul 29 - Jul 30
includes taxes & fees
9/10 Wonderful! (1,079 reviews)
"Staff was very friendly and welcoming. Assistant Front Desk Manager Mr. Flamming was very accommodating with providing me with a complimentary room upgrade and his gesture was very appreciated. Devon at Pelican Beach Grill was very attentive and accommodating especially when I had little time for ..."

Reviewed on Jul. 3, 2025

Hilton Vacation Club Flamingo Beach St. Maarten
See all 426 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

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
Kim Sha Beach

Kim Sha Beach

4/5(17 reviews)

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

What to do in Simpson Bay

Little Bay

Anguilla Getaway Cruise

CA $191
per adult
90% of travellers recommend
Anguilla Getaway Cruise
Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

CA $205
per adult
80% of travellers recommend
Ultimate Prickly Pear and Anguilla Experience
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

Frequently asked questions

How much does a Simpson Bay vacation package cost?
You'll find cheap prices from CA $853 on Expedia for your Simpson Bay escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Simpson Bay costs.
What are the cheapest months to go to Simpson Bay?
If you're hoping to snag a cheap Simpson Bay vacation package, consider visiting in September, October and November. You'll usually find better rates on airfares and hotels during these months --- ideal for travellers wishing to save money.
How many days is enough for Simpson Bay?
Simpson Bay vacations can be as short or long as you like, but to get a true feel for this destination, we'd suggest 4 days is a good ballpark. This will mean you can visit top sights like Great Bay Beach and Grand Case Beach as well as hidden gems. Don't miss out on cool areas such as Pelican Key and Upper Prince's Quarter either. If you're clever with your time, you may even be able to take a day trip or two from Simpson Bay too.
Is it worth booking a vacation package to Simpson Bay?
Boasting a host of highlights starting with its amazing coastal beaches, Simpson Bay is a good vacation destination. Whether you'd like to visit attractions such as Simpson Bay Beach and Flamingo Beach or venture off the beaten track, you'll have loads to keep you busy during your Simpson Bay vacation.
How to find the best Simpson Bay package deals?
Start your search for a Simpson Bay package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Simpson Bay package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Simpson Bay escape off to a flying start.
Is it cheaper to book a Simpson Bay vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component separately. And you'll still get the flexibility to create a tailored Simpson Bay vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Simpson Bay?
If you've got your Simpson Bay vacation dates confirmed, book as early as you can to snap up some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Simpson Bay?

  1. Choose when to go: Check your schedule and get your bags packed. Your favourite time of year and the type of activities on offer will also help you decide when to vacation in Simpson Bay.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and food to flights and activities. Your accommodations will likely be the largest expense during your trip to Simpson Bay.
  3. Determine how many days away: Start by listing all the attractions you want to get to in Simpson Bay. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalized Simpson Bay vacation package.

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