Simpson Bay Vacation Rentals

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Our top choices for Simpson Bay vacation rentals

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.8 out of 10, Excellent, (61)
"Enjoyed my stay "
United States
Shakia
$298 nightly
The price is $312
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Hills Residence

Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten
4.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (1166)
"Room was great, resort was great, staff was great"
Canada
Gisele
$408 nightly
The price is $428
Jan 6 - Jan 7, 2026
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten

FLAMINGO BEACH

FLAMINGO BEACH
3.5 star property
Pelican Key
FLAMINGO BEACH

Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.0 out of 10, Good, (127)
"No issues. Staff were very welcoming and accommodating. Was a pleasant stay. "
United States
Sharmain
$181 nightly
The price is $189
Jan 4 - Jan 5, 2026
Total with taxes and fees
Simpson Bay Suites

1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Simpson Bay
10.0 out of 10, Exceptional, (2)
"perfect!!"
United States
jason l.
$314 nightly
The price is $324
Jan 6 - Jan 7, 2026
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
2.0 star property
Simpson Bay
$349 nightly
The price is $361
Jan 5 - Jan 6, 2026
Total with taxes and fees
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

B226 - Amazing Lagoon View with Balcony

B226 - Amazing Lagoon View with Balcony
Sint Maarten
$348 nightly
The price is $369
Jan 9 - Jan 10, 2026
Total with taxes and fees
B226 - Amazing Lagoon View with Balcony

B254 - Cozy Apartment in the Heart of Simpson Bay

B254 - Cozy Apartment in the Heart of Simpson Bay
Sint Maarten
$351 nightly
The price is $372
Jan 27 - Jan 28, 2026
Total with taxes and fees
B254 - Cozy Apartment in the Heart of Simpson Bay

C337 - Charming 2-Bedroom Lagoon View

C337 - Charming 2-Bedroom Lagoon View
2.0 star property
Sint Maarten
$427 nightly
The price is $454
Jan 3 - Jan 4, 2026
Total with taxes and fees
C337 - Charming 2-Bedroom Lagoon View

C302 – Modern Comfort with Private Terrace

C302 – Modern Comfort with Private Terrace
2.0 star property
Simpson Bay
$341 nightly
The price is $362
Jan 9 - Jan 10, 2026
Total with taxes and fees
C302 – Modern Comfort with Private Terrace

D414 – 1-Bedroom Apartment with Balcony

D414 – 1-Bedroom Apartment with Balcony
2.0 star property
Sint Maarten
D414 – 1-Bedroom Apartment with Balcony

Marina Views in the Heart of Simpson Bay

Marina Views in the Heart of Simpson Bay
Simpson Bay
10.0 out of 10, Exceptional, (1)
"We loved this place so much we bought it! The location is to die for. Right in the heart of Simpson Bay, there is soooo much to see and do right around you. The beach is literally a four minute walk and the water is calm and beautiful. We can’t wait to come back again and again! Also, Kayla, the manager is the best to work with. Sweet and helpful."
United States
Trish S.
$496 nightly
The price is $517
Jan 11 - Jan 12, 2026
Total with taxes and fees
Marina Views in the Heart of Simpson Bay

Turquoise paradise, directly ON beach, gated w underground parking!

Turquoise paradise, directly ON beach, gated w underground parking!
Simpson Bay
9.8 out of 10, Exceptional, (20)
"This is the perfect place to stay location wise and with the beach views! Also there is a/c in each room which is super nice! "
United States
Rachel S.
$632 nightly
The price is $632
Jan 2 - Jan 3, 2026
Total with taxes and fees
Turquoise paradise, directly ON beach, gated w underground parking!

C316 - Lagoon view with balcony

C316 - Lagoon view with balcony
Simpson Bay
$351 nightly
The price is $372
Jan 11 - Jan 12, 2026
Total with taxes and fees
C316 - Lagoon view with balcony

D408 – Chic & Stylish 2 Bedroom with Terrace

D408 – Chic & Stylish 2 Bedroom with Terrace
2.0 star property
Sint Maarten
$429 nightly
The price is $456
Jan 16 - Jan 17, 2026
Total with taxes and fees
D408 – Chic & Stylish 2 Bedroom with Terrace

D426 - Beautiful view of the lagoon with balcony

D426 - Beautiful view of the lagoon with balcony
2.0 star property
Simpson Bay
$357 nightly
The price is $378
Jan 7 - Jan 8, 2026
Total with taxes and fees
D426 - Beautiful view of the lagoon with balcony

A102 - Cozy Apartment with Garden

A102 - Cozy Apartment with Garden
Sint Maarten
$341 nightly
The price is $362
Jan 13 - Jan 14, 2026
Total with taxes and fees
A102 - Cozy Apartment with Garden

A116 - Immersive Simpson Bay Lagoon View

A116 - Immersive Simpson Bay Lagoon View
Sint Maarten
$348 nightly
The price is $369
Jan 21 - Jan 22, 2026
Total with taxes and fees
A116 - Immersive Simpson Bay Lagoon View

A101 - Outstanding Lagoon View & Garden

A101 - Outstanding Lagoon View & Garden
Sint Maarten
$399 nightly
The price is $424
Jan 24 - Jan 25, 2026
Total with taxes and fees
A101 - Outstanding Lagoon View & Garden

Sunny Days at Simpson Bay Yacht Club

Sunny Days at Simpson Bay Yacht Club
Simpson Bay
10.0 out of 10, Exceptional, (2)
"This is a great location to come to: comfortable central location lots to do around restaurant everything you would need in a getaway I will definitely here again"
United States
JEROME J.
$1,021 nightly
The price is $1,066
Jan 16 - Jan 17, 2026
Total with taxes and fees
Sunny Days at Simpson Bay Yacht Club
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.
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Top Simpson Bay Hotel Reviews

Price trends for vacation rentals in Simpson Bay

Less expensive
More expensive
Next month
September
January
$406
Month
Price
January
$406
February
$366
March
$395
April
$372
May
$283
June
$276
July
$280
August
$281
September
$215
October
$215
November
$246
December
$373
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Simpson Bay. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Simpson Bay

Everything you need to know about Simpson Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simpson Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simpson Bay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Simpson Bay vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simpson Bay. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Simpson Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $189 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Simpson Bay rentals

At Expedia, we put the best Simpson Bay vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Simpson Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simpson Bay vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simpson Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Simpson Bay?

Yes, we give you a choice of vacation rentals near top attractions in Simpson Bay, or you can choose a secluded option if you'd like a relaxing place to stay. Visitors like the array of shops and popular beaches in Simpson Bay. While you're here, grab a bite or have a drink at the lively bars and top-notch restaurants.

What are some of the best vacation home rentals that Simpson Bay has to offer?

Caribbean Sea Studio next to The Morgan Resort: Visitors like this Simpson Bay vacation home rental. It is located on the beach and has an outdoor pool, a patio, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a hot tub. Other favorite homes for rent in Simpson Bay are Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool and Charming 3BR Villa w Private Pool in Pelican Key.

How many vacation rentals are there in Simpson Bay?

With 41 Expedia vacation rentals, you're sure to find just the right place for your Simpson Bay stay.

What’s there to see and do in Simpson Bay?

Kim Sha Beach and Flamingo Beach are a couple of lovely local spots to get outside and enjoy nature. Simpson Bay Beach and Hollywood Casino are other places to visit while you're in town.

What’s a vacation rental in Simpson Bay like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Simpson Bay. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for families.