Simpson Bay Vacations from $1,054
Book a Hotel + Flight or Car together to unlock savings
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.
The Latest Simpson Bay vacation packages
Price found within the past 48 hours. Click for updated prices.
The Villas at Simpson Bay Resort
Pelican Key
$1,185
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
9.2/10 Wonderful! (1,525 reviews)
I couldn’t say enough about villas at Simpson bay. From the spacious rooms, helpful and courteous staff to the well maintained grounds. Thank you to all staff and specially the ladies at the front desk. TO ALL STAFF EXCELLENT SERVICES!!! Thank you.
Reviewed on Sep 3, 2026
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
$1,089
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
9.2/10 Wonderful! (1,001 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
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See all available trips from Columbus to Simpson Bay
View all tripsStay near popular Simpson Bay attractions
Kim Sha Beach
8.8/10 (591 reviews)
Kim Sha Beach offers pristine white sands and turquoise waters ideal for families and water sports enthusiasts. Enjoy jet skiing or kayaking, then explore the vibrant restaurants and nightlife of nearby Simpson Bay.
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)
Simpson Bay Beach offers pristine white sand and tranquil waters along one of Sint Maarten's longest shorelines. Enjoy peaceful sunbathing or swimming, with nearby beach bars for refreshments.
Flamingo Beach
9.0/10 (768 reviews)
Pristine white sands and turquoise waters define this quintessential Caribbean escape in Simpson Bay. Enjoy swimming in gentle waves or snorkeling the clear waters before watching a spectacular sunset.
Lay Bay Beach
8.4/10 (212 reviews)
Lay Bay Beach offers a tranquil escape between Simpson Bay and Maho on Sint Maarten's Dutch side. Bring your own supplies to this serene, undeveloped stretch of sand for genuine beachside peace.
Dunes Casino
8.0/10 (249 reviews)
This relaxed casino offers over 200 slot machines and electronic games in a laid-back atmosphere. Enjoy the sportsbook lounge with flat-screen TVs while placing bets in this intimate gaming venue.
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
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
$159
per adult
90% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
$77
per adult
94% of travellers recommend
Simpson Bay Hotel Deals
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
Fully refundableReserve now, pay when you stay
$152 nightly
$176 total
Sep 5 - Sep 6
Total with taxes and fees
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
$444 nightly
$466 total
Oct 5 - Oct 6
Total with taxes and fees
Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
Fully refundableReserve now, pay when you stay
$135 nightly
$142 total
Sep 11 - Sep 12
Total with taxes and fees
9.2/10 Wonderful! (1,738 reviews)
"Best time definitely coming back ‼️"
Reviewed on Sep 3, 2026
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.
Find the Best Simpson Bay Vacation Packages
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 center on your trip to Simpson Bay, find a hotel around Simpson Bay Beach (just 1 mile 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.
Simpson Bay Essential Information
Language | Dutch |
|---|---|
Currency | Netherlands Antillean guilders |
Local Welcome | Hallo |
Local Goodbye | Dag |
Closest Airport | Princess Juliana Intl. Airport (SXM) |
Max Temp Winter | 80ºF |
Max Temp Summer | 80ºF |
Top Sights | Maho Beach, Mullet Bay Beach and Cupecoy Beach |
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Frequently asked questions
How much does a Simpson Bay vacation package cost?
You'll find cheap prices from $1,054 on Expedia for your Simpson Bay getaway. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Simpson Bay costs.
What are the cheapest months to go to Simpson Bay?
September, November and December are great times to look for cheap Simpson Bay vacation packages. Choosing to travel in less busy months means you can generally find lower prices on accommodations and flights.
How many days is enough for Simpson Bay?
Allow at least 4 days for your Simpson Bay vacation to really immerse yourself in all that makes this place special. Wander around popular neighborhoods, including Cay Bay Hill and Little Bay. Then make a beeline for major sights like Lay Bay Beach and Hollywood Casino. With a good itinerary, you'll be kept busy with room for some rest time too. Want to travel outside of Simpson Bay? Consider squeezing in an excursion or two.
Is it worth booking a vacation package to Simpson Bay?
From leading attractions such as Simpson Bay Beach and Kim Sha Beach to its epic coastal beaches, a Simpson Bay vacation guarantees an unforgettable adventure. With so much to see and do, find out for yourself why Simpson Bay is such a good vacation destination.
How to find the best Simpson Bay package deals?
Start your search for a Simpson Bay package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Simpson Bay package deal right away, just change 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 adventure off to a flying start.
Is it cheaper to book a Simpson Bay vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging stays and flights individually. Better still, you can customize your Simpson Bay escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Simpson Bay?
If you're considering a spontaneous Simpson Bay trip, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Simpson Bay?
- Choose your travel dates: The things you plan to do in Simpson Bay and your preferred season can help you decide when to go.
- Plan your budget wisely: Besides the price of your hotel, you should consider other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Simpson Bay.
- Use Expedia's trip planning tool to discover Simpson Bay: Research every part of your trip to Simpson Bay with this handy planner. Invite family or friends to collaborate on a group trip, search for stays or things to do and make bookings.
- Decide how many days away: Start by making a list of all the activities and attractions you'd like to experience in Simpson Bay. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to find a Simpson Bay vacation package that brings all your bookings together.
- Add on experiences and excursions: Read our dedicated travel guide to find some awesome things to do in Simpson Bay. Book tickets or make reservations in advance to save time and avoid the hassle of trying to find activities when you arrive.
Does Expedia offer Book Now, Pay Later Simpson Bay vacation packages?
Your Simpson Bay getaway should be a relaxing escape from your busy life, not a reason for money worries. So to allow you that extra flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.