Cheap Flights to Simpson Bay from $38

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How Much Does it Cost To Fly To Simpson Bay?

The cheapest prices found with in the last 7 days for return flights were $158 and $38 for one-way flights to Simpson Bay for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
FLLSimpson BayMarch 24 to March 31$172
PHLSimpson BayFebruary 9 to February 13$201
BOSSimpson BayFebruary 9 to February 13$201
LGASimpson BayFebruary 9 to February 14$209
EWRSimpson BayFebruary 9 to February 14$211
MIASimpson BayFebruary 21 to February 28$234
YYZSimpson BayMarch 2 to March 10$304
JFKSimpson BayFebruary 24 to February 28$308
YULSimpson BayMarch 26 to April 2$360
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
FLLSimpson BayFebruary 1 to February 7$174
BOSSimpson BayFebruary 1 to February 12$246
PHLSimpson BayJanuary 31 to February 14$266
EWRSimpson BayJanuary 31 to February 13$268
EWRSimpson BayJanuary 31 to February 13$268
MIASimpson BayJanuary 31 to February 2$351
JFKSimpson BayFebruary 1 to February 8$352
YYZSimpson BayJanuary 31 to February 5$401
YULSimpson BayJanuary 31 to February 9$437
*Prices include taxes and fees

Simpson Bay Flight Information

Traveling to
Simpson Bay
Lowest Price
$158
Number of Airlines Serving
Airlines Serving
Frontier Airlines
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing Simpson Bay Accommodation Deals

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
$322 nightly
The price is $338 total per night from Feb 15 to Feb 16
$338 total
Feb 15 - Feb 16
Total with taxes and fees
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. ...
9/10 Wonderful! (1,421 reviews)
The room was SO CLEAN!! I have OCD and I Lysol wiped all the shelves before putting any of my things down and not a speck of dirt was seen on the bright white wipe. 90% of the staff were so pleasant, only a few older men were grumpy and obviously not happy. Other than that, we were treated wonderfully. ...

Reviewed on Jan 20, 2026

Opens in a new windowHilton Vacation Club Flamingo Beach St. Maarten
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
$398 nightly
The price is $416 total per night from Feb 7 to Feb 8
$416 total
Feb 7 - Feb 8
Total with taxes and fees
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (1,577 reviews)
We never did the breakfast, but we did order a room service pizza couple times which was more affordable than eating at the restaurants nearby. It would be nice if there was music around the pool room service was great. Our rooms were clean zero complaints on that. The roads around the property definitely ...

Reviewed on Jan 19, 2026

Opens in a new windowSimpson Bay Resort, Marina & Spa
Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
115 Welfare Road Simpson Bay
$370 nightly
The price is $388 total per night from Feb 12 to Feb 13
$388 total
Feb 12 - Feb 13
Total with taxes and fees
Book a stay at this beach aparthotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ...
9/10 Wonderful! (1,172 reviews)
We had an ocean view. Staff friendly and very helpful. Nice beach area. Everything we needed we could walk to

Reviewed on Jan 22, 2026

Opens in a new windowHilton Vacation Club Royal Palm St. Maarten
Save an average of 15% on thousands of hotels when you're signed in
Travel Inn Hotel

Travel Inn Hotel

3 out of 5
Airport Road 15 Simpson Bay
$127 nightly
The price is $133 total per night from Jan 25 to Jan 26
$133 total
Jan 25 - Jan 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Simpson Bay. Enjoy free parking, room service, and a 24-hour front desk. Popular attractions Maho Beach and Orient ...
6.6/10 (451 reviews)
I chose this hotel as it had an inexpensive room for a last-minute booking. It's a good place to stay for 1 night, it's an easy walking distance to plenty of restaurants, bars and shops. It's not a

Reviewed on Jan 17, 2026

Opens in a new windowTravel Inn Hotel
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.

Luxury Hotels in Simpson Bay

Villa Bianca

Villa Bianca

4.5 out of 5
Ruby Drive, Pelican Key Simpson Bay
Book a stay at this luxury villa in Simpson Bay. Enjoy free WiFi, free parking, and private pools. Popular attractions Maho Beach and Mullet Bay Beach are located ...
Opens in a new windowVilla Bianca
Mary's Boon Beach Resort & Spa

Mary's Boon Beach Resort & Spa

3 out of 5
117 Simpson Bay Road Simpson Bay
$177 nightly
The price is $185 total per night from Feb 9 to Feb 10
$185 total
Feb 9 - Feb 10
Total with taxes and fees
Book a stay at this beach hotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the restaurant and the helpful staff ...
8.6/10 Excellent! (1,001 reviews)
Excellent staff, overall experience was great. Can’t wait to return

Reviewed on Jan 23, 2026

Opens in a new windowMary's Boon Beach Resort & Spa
The Atrium Beach Resort and Spa, an Ascend Collection Resort

The Atrium Beach Resort and Spa, an Ascend Collection Resort

3 out of 5
6 Billy Folly Road Simpson Bay
$483 nightly
The price is $503 total per night from Jan 26 to Jan 27
$503 total
Jan 26 - Jan 27
Total with taxes and fees
Book a stay at this beach hotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (1,000 reviews)
Outstanding Performance 👍

Reviewed on Jan 19, 2026

Opens in a new windowThe Atrium Beach Resort and Spa, an Ascend Collection Resort
Save an average of 15% on thousands of hotels when you're signed in
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
$398 nightly
The price is $416 total per night from Feb 7 to Feb 8
$416 total
Feb 7 - Feb 8
Total with taxes and fees
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (1,577 reviews)
We never did the breakfast, but we did order a room service pizza couple times which was more affordable than eating at the restaurants nearby. It would be nice if there was music around the pool room service was great. Our rooms were clean zero complaints on that. The roads around the property definitely ...

Reviewed on Jan 19, 2026

Opens in a new windowSimpson Bay Resort, Marina & Spa
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.

Family Friendly Hotels in Simpson Bay

Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
115 Welfare Road Simpson Bay
$370 nightly
The price is $388 total per night from Feb 12 to Feb 13
$388 total
Feb 12 - Feb 13
Total with taxes and fees
Book a stay at this beach aparthotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ...
9/10 Wonderful! (1,172 reviews)
We had an ocean view. Staff friendly and very helpful. Nice beach area. Everything we needed we could walk to

Reviewed on Jan 22, 2026

Opens in a new windowHilton Vacation Club Royal Palm St. Maarten
Simpson Bay Resort, Marina & Spa
Great for families

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
$398 nightly
The price is $416 total per night from Feb 7 to Feb 8
$416 total
Feb 7 - Feb 8
Total with taxes and fees
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (1,577 reviews)

Families like: Outdoor pools, kitchen, playground, babysitting

Travelers say...
We never did the breakfast, but we did order a room service pizza couple times which was more affordable than eating at the restaurants nearby. It would be nice if there was music around the pool room service was great. Our rooms were clean zero complaints on that. The roads around the property definitely ...

Reviewed on Jan 19, 2026

Opens in a new windowSimpson Bay Resort, Marina & Spa
The Villas at Simpson Bay Resort
Great for families

The Villas at Simpson Bay Resort

4 out of 5
Billy Folly Road No. 37A Simpson Bay
$499 nightly
The price is $520 total per night from Feb 1 to Feb 2
$520 total
Feb 1 - Feb 2
Total with taxes and fees
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our ...
9.2/10 Wonderful! (1,365 reviews)

Families like: Outdoor pools, waterslide, playground, babysitting

Travelers say...
Staff and facilities, including dining options all excellent

Reviewed on Jan 18, 2026

Opens in a new windowThe Villas at Simpson Bay Resort
Save an average of 15% on thousands of hotels when you're signed in
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
$322 nightly
The price is $338 total per night from Feb 15 to Feb 16
$338 total
Feb 15 - Feb 16
Total with taxes and fees
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. ...
9/10 Wonderful! (1,421 reviews)
The room was SO CLEAN!! I have OCD and I Lysol wiped all the shelves before putting any of my things down and not a speck of dirt was seen on the bright white wipe. 90% of the staff were so pleasant, only a few older men were grumpy and obviously not happy. Other than that, we were treated wonderfully. ...

Reviewed on Jan 20, 2026

Opens in a new windowHilton Vacation Club Flamingo Beach St. Maarten
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.

Best Simpson Bay Flight and Hotel Packages

Simpson Bay flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel
The Villas at Simpson Bay Resort
Simpson Bay Resort, Marina & Spa
Don't see what you're looking for?
See all available trips from Boston to Simpson Bay
View all trips

Simpson Bay flight + hotel packages - premium economy flights

Price found within the past 48 hours. Click for updated prices.
Sonesta Maho Beach All Inclusive Resort Casino & Spa
The Villas at Simpson Bay Resort
Simpson Bay Resort, Marina & Spa
Don't see what you're looking for?
See all available trips from New York to Simpson Bay
View all trips

Simpson Bay flight + hotel packages - business class flights

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel
The Villas at Simpson Bay Resort
Panorama Residences at Monte Vista
Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Simpson Bay
View all trips

Simpson Bay flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
Horizon View Beach Hotel
Princess Heights Luxury Boutique Condo Hotel
Oceans at Divi Little Bay
Don't see what you're looking for?
See all available trips from Boston to Simpson Bay
View all trips

Need a Car For After Your Flight?

Lowest prices found within the past 4 days. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Which airlines fly to Simpson Bay?
Book your ticket with one of the 16 airlines that fly to Simpson Bay and enjoy a wonderful new adventure. Carriers with outstanding reviews include:

  • Winair
  • American Airlines
  • Anguilla Air Services

What airport is best to fly into Simpson Bay?
There's no need for you to look up flight options into numerous airports when jetting into Simpson Bay. Princess Juliana Intl. Airport (SXM) is the city's sole airport, and is located 1 mi from all the action downtown.
Where to stay in Simpson Bay
With 2,082 wonderful properties in Simpson Bay, your options are many and varied. But don't drag your feet. The sooner you book, the sooner you can start counting down the days until your adventure!There's no more opportune time to truly indulge yourself than when you're taking a vacation. Lock in a room at the Simpson Bay Penthouse and feel like a VIP during your stay. Simpson Bay also features accommodations that won't break the budget. Check out the Travel Inn Hotel if you would rather keep those pennies in your pocket.
Places to visit in Simpson Bay
If you're planning on staying in this lively metropolis, you'll want to add Maho Beach to your travel schedule. It's one of the most noteworthy attractions in the city.Breathe in the salty, fresh air and listen to the crashing of the waves at Mullet Bay Beach. Want some more ideas? Clear your mind and tune in to the sounds of the seabirds encircling you at Kim Sha Beach. But there's more. Pack a delicious picnic and spend an entire day admiring the waves and tasting the salty air at Cupecoy Beach.
How to get through airport security fast when traveling to Simpson Bay
If you like the idea of spending more time at the airport cafes and less time at the security checkpoint on your way to Simpson Bay, just follow these handy tips:

  • Make sure you know the location of your travel ID and boarding pass. You don't want to hold up the line when you're asked to produce them.
  • Take off your shoes and belt before approaching security. Items such as these are not allowed to pass through the body scanner.
  • All laptops must be removed from their carry bags and placed in a tub before X-raying.
  • Toothpaste, lip balm and other toiletry items in gel, liquid or cream form need to be stored in containers smaller than 3.4 ounces (100 milliliters). They also need to fit in a 1-quart (1-liter) clear zip-lock plastic bag.
  • Airport security personnel may ask you to remove your shoes before entering the body scanner. Choose a pair that you can take off easily. There's nothing more tiresome than having to do your laces up again and again.
  • The list of prohibited items is forever changing. Read over your carrier's official website for what is not allowed on board their aircraft.

Plane Tickets To Simpson Bay

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Simpson Bay. Browse through our inventory to explore a wide range of cheap flights to Simpson Bay to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Simpson Bay as you anxiously await to exit the plane and explore what Simpson Bay has to offer. Considering all the amazing local food and culture in Simpson Bay, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Simpson Bay to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Simpson Bay without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Simpson Bay with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Simpson Bay today!

Explore More Ways to Travel with Travelocity

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.