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
Oyster Pond
CA $1,369
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,003 reviews)
The property was beautiful, clean and the staff was impeccable! They put a bottle of wine in my room on my birthday. The front desk was amazing and also the housekeepers.
Reviewed on Aug 13, 2026
The Morgan Resort Spa Village
CA $2,357
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (2,341 reviews)
The Morgan was amazing! The pool is great and the staff as well. Very attentive to guest needs. The only thing was the rooms get extremely cold with the AC but everything is 10/10!
Reviewed on Aug 15, 2026
Sonesta Ocean Point All Inclusive, Adults Only Resort
CA $3,057
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,003 reviews)
Best trip every clean hotel great staff and location was amazing definitely recommend this hotel to anybody
Reviewed on Aug 13, 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?
Simpson Bay Hotel Deals
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
CA $611
CA $753 total
Sep 15 - Sep 16
includes taxes & fees
9/10 Wonderful! (2,349 reviews)
"The Morgan was amazing! The pool is great and the staff as well. Very attentive to guest needs. The only thing was the rooms get extremely cold with the AC but everything is 10/10!"
Reviewed on Aug 15, 2026
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
Fully refundableReserve now, pay when you stay
CA $217
CA $264 total
Sep 9 - Sep 10
includes taxes & fees
Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
Fully refundableReserve now, pay when you stay
CA $153
CA $197 total
Sep 1 - Sep 2
includes taxes & fees
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.
Stay near popular Simpson Bay attractions
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.
Hollywood Casino
8.2/10 (583 reviews)
Bingo, a handful of gambling tables, buffets and piano bars entertain the public at this almost intimate gambling hall.
Simpson Bay Beach
9.2/10 (1,834 reviews)
Why not spend a lazy afternoon at Simpson Bay Beach during your trip to Simpson Bay? Check out the shops and lively bars in this romantic area.
Flamingo Beach
9.0/10 (768 reviews)
Why not spend a lazy afternoon at Flamingo Beach during your trip to Simpson Bay? Stroll along the beautiful beaches or visit the shops in this romantic area.
Lay Bay Beach
8.4/10 (212 reviews)
Why not spend a lazy afternoon at Lay Bay Beach during your trip to Simpson Bay?
Dunes Casino
8.0/10 (249 reviews)
Why not roll the dice with a visit to Dunes Casino during your travels in Beacon Hill? Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.
Market Garden Supermarket
9.4/10 (8 reviews)
You can find the perfect gifts to bring home at Market Garden Supermarket during your stay in Simpson Bay. Check out the shops and lively bars in this romantic area.
What to do in Simpson Bay
Half Day Snorkeling Adventure
CA $91
per adult
100% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
CA $190
per adult
90% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
CA $120
per adult
94% of travellers recommend
Frequently asked questions
How much does a Simpson Bay vacation package cost?
You'll find cheap prices from CA $1,369 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?
- 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.
- 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.
- 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.
- 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
- Resorts in Simpson Bay
- Indigo Oceanview Terrace
- Simpson Bay Hotels
- All Inclusive Resorts and in Sint Maarten
- Sint Maarten Hotels
- The Atrium Beach Resort and Spa
- Port de Plaisance Resort
- Maho Beach House
- Cole Bay Hotels
- Hotels near Flamingo Beach
- Condostmaarten by the sea
- Hotels near Kim Sha Beach
- Pelican Key Hotels
- One Hundred Million Dollar Yacht On Land 5 star Villa Namaste on the Ocean
- Beachfront DESIGN VILLA
- Cheap Hotels in Simpson Bay
- Hotels near Princess Juliana Intl.
- Luxury Hotels in Simpson Bay
- Maho Beach Escape; Sunset Ocean View
- Logan's Run St Maarten
- 5 Star Hotels in Simpson Bay
- Flights from Basseterre (SKB) to Philipsburg (SXM)
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- Flights from Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
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- Flights to Princess Juliana Intl.
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- Flights from Calgary (YYC) to Philipsburg (SXM)
- Flights to Sint Maarten
- Flights from New York (JFK) to Philipsburg (SXM)
- Flights to Simpson Bay
- Flights from Cancun (CUN) to Philipsburg (SXM)
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- Flights from Miami (MIA) to Philipsburg (SXM)
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- Visit Cole Bay
- Lowlands Vacations
- Kim Sha Beach
- Visit Sint Maarten
- Cupecoy Vacations
- Mullet Bay Beach
- Sint Maarten Vacations
- Museum of Sint Maarten
- American University of the Caribbean
- Visit Simpson Bay
- Great Bay Beach
- University of St. Martin
- Casino Royale
- Philipsburg Vacations
- Fort Amsterdam
- Guana Bay Beach
- All inclusive Vacation Packages Sint Maarten
- Hollywood Casino
- Visit Pelican Key
- Maho Reef Vacations
- Maho Beach
- Rent A Wreck Rental Cars in Princess Juliana Intl.
- Enterprise Rental Cars in Princess Juliana Intl.
- Rental cars Princess Juliana Intl. airport
- Kk Leisure Rental Cars in Princess Juliana Intl.
- Hertz Rental Cars in Princess Juliana Intl.
- Avis Rental Cars in Princess Juliana Intl.
- Budget Rental Cars in Princess Juliana Intl.
- Ace Rental Cars in Princess Juliana Intl.
- Car rental Sint Maarten
- Car rental Simpson Bay
- Thrifty Car Rental Rental Cars in Princess Juliana Intl.
- National Car Rental Rental Cars in Princess Juliana Intl.
- Luxury Car Rentals near Princess Juliana Intl.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
