Simpson Bay Vacation Packages

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

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.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $3,042, price is now CA $1,534 per person
CA $1,534
per person
Sep 7 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,429 reviews)
Our stay at Simpson Bay Villa was beautiful. The property was beautiful, well maintained. Right on the water and everything was very close by. Restaurants were in walking distance, supermarkets were close by. There was really no reason to leave the resort. Even if you wanted to do tours or visit other islands it was very convenient from this villa. We had a one bedroom apartment, full kitchen, living room just like being at home. There was absolutely nothing to complain about on vacation. Staff was very friendly and helpful with anything we asked. Trust me this is vacation spot you’ll not regret

Reviewed on Jun 30, 2026

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was CA $3,072, price is now CA $2,120 per person
CA $2,120
per person
Aug 8 - Aug 15
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.4/10 Exceptional! (736 reviews)
Such a great stay here! Everyone is friendly and willing to give you all the great recommendations. I loved my time here and can’t wait to come back!

Reviewed on Jun 27, 2026

Hotel La Plantation

Hotel La Plantation

4 out of 5
Price was CA $2,535, price is now CA $1,819 per person
CA $1,819
per person
Aug 8 - Aug 15
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
8.8/10 Excellent! (624 reviews)
The Staff service was excellent. Rooms were cleaned every day. Breakfast bar was good.

Reviewed on Jun 30, 2026

Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was CA $2,839, price is now CA $2,088 per person
CA $2,088
per person
Aug 8 - Aug 15
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
8.6/10 Excellent! (533 reviews)
The location was amazing. Restaurant and beaches were superb! Our pool needed a good cleaning with some algae on the walls but otherwise a perfect location

Reviewed on Jun 18, 2026

Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was CA $3,137, price is now CA $2,355 per person
CA $2,355
per person
Aug 8 - Aug 15
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
8.2/10 Very good! (442 reviews)
This resort won't disappoint you. The suites at Oceans at Divi Little Bay are clean and they look just like the pictures! Rest assured!! The food is delicious!! Do yourself a favor and book this resort.

Reviewed on Jun 30, 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

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road Simpson Bay
The price is CA $441 per night from Jul 29 to Jul 30
CA $441
CA $558 total
Jul 29 - Jul 30
includes taxes & fees
9/10 Wonderful! (2,247 reviews)
"LOVED LOVED LOVED MY STAY !!"

Reviewed on Jun 30, 2026

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
The price is CA $347 per night from Jul 14 to Jul 15
CA $347
CA $426 total
Jul 14 - Jul 15
includes taxes & fees
9/10 Wonderful! (1,840 reviews)
"Room was clean and enough room for my wife and I and our two girls (6 and 10). Pullout bed was plenty comfortable. Room was a little warm, as the mini split wall unit didn’t seem strong enough to cool the room adequately, but there were two strong ceiling fans. Kids enjoyed the shallower pools. Bartenders ..."

Reviewed on Jul 1, 2026

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 $170 per night from Jul 19 to Jul 20
CA $170
CA $216 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (1,626 reviews)
"We all had a great time! Amazing beach front view and our room was spacious and clean. Everyone was very helpful especially Joanna at the front desk."

Reviewed on Jul 1, 2026

Hilton Vacation Club Flamingo Beach St. Maarten
See all 447 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

Stay near popular Simpson Bay attractions

A beach with colorful play structures, a lifeguard tower, and a row of red kayaks.

Kim Sha Beach

8.8/10 (591 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.
See properties

What to do in Simpson Bay

Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

CA $90
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
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
High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

CA $103
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
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 $1,534 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.

Explore a world of travel with Expedia

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