Simpson Bay Vacation Rentals

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Vacation Rentals in Simpson Bay

Outdoor pool, sun loungers
Hilton Vacation Club Royal Palm St. Maarten

Aparthotel in Simpson Bay

4.0 star property
9.0 out of 10, Wonderful, (1157)
"One of my favorite places to stay."
United States
Carlos
$174 nightly
The price is $183
Dec 17 - Dec 18
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten
Amazing Top Floor Apartment | Balcony
The Hills Residence

Aparthotel in Simpson Bay

3.0 star property
8.8 out of 10, Excellent, (51)
"Enjoyed my stay "
United States
Shakia
$254 nightly
The price is $266
Dec 17 - Dec 18
Total with taxes and fees
The Hills Residence
Exterior
FLAMINGO BEACH

Aparthotel in Pelican Key

3.5 star property
$461 nightly
The price is $482
Dec 7 - Dec 8
Total with taxes and fees
FLAMINGO BEACH
Pool
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

Apartment in Simpson Bay

10.0 out of 10, Exceptional, (1)
"Communication with the host was very easy. The location is outstanding and the facility has every amenity. You can imagine. I highly recommend this property and can’t wait to visit again."
United States
Richard S.
$231 nightly
The price is $237
Dec 7 - Dec 8
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Smart TV, stereo, offices
Marina Views in the Heart of Simpson Bay

Apartment in 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.
$330 nightly
The price is $344
Dec 7 - Dec 8
Total with taxes and fees
Marina Views in the Heart of Simpson Bay
Beach nearby, white sand, sun loungers, beach umbrellas
Simpson Bay Suites

Aparthotel in Simpson Bay

3.5 star property
6.8 out of 10, (125)
"No issues. Staff were very welcoming and accommodating. Was a pleasant stay. "
United States
Sharmain
$163 nightly
The price is $170
Dec 15 - Dec 16
Total with taxes and fees
Simpson Bay Suites
Property grounds
Maho Beach House - Petit Studio Océanique - Charmante Vue

Condo in Maho, Sint Maarten

9.0 out of 10, Wonderful, (2)
"Very close to the sunset bar and interesting views of approaching aircraft. Excellent sunset views from the Sunset bar or the Morgan resort on the other side of the unit. Morgan resort also had excellent dining area and bar facilities open to the public."
United States
Roy N.
$231 nightly
The price is $231
Dec 7 - Dec 8
Total with taxes and fees
Maho Beach House - Petit Studio Océanique - Charmante Vue
Beach
Pirates Booty - Beach Bar Studio next to The Morgan Resort

Condo in Simpson Bay

8.6 out of 10, Excellent, (4)
"Welcoming love the area we will be coming back thank you so much "
United States
Juan D.
$242 nightly
The price is $242
Dec 7 - Dec 8
Total with taxes and fees
Pirates Booty - Beach Bar Studio next to The Morgan Resort
Exterior
Oceanview Escape in Sint Maarten

Condo in Pelican Key

$474 nightly
The price is $495
Dec 8 - Dec 9
Total with taxes and fees
Oceanview Escape in Sint Maarten
Property grounds
The Best Little Beach Bar Condo in Maho - next to The Morgan Resort

Condo in Maho

9.0 out of 10, Wonderful, (6)
"Awsome location "
United States
todd
$248 nightly
The price is $248
Dec 7 - Dec 8
Total with taxes and fees
The Best Little Beach Bar Condo in Maho - next to The Morgan Resort
Pool
Sunny Days at Simpson Bay Yacht Club

Condo in 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.
$511 nightly
The price is $533
Dec 10 - Dec 11
Total with taxes and fees
Sunny Days at Simpson Bay Yacht Club
Property grounds
Caribbean Sea Studio next to The Morgan Resort

Vacation Home in Maho, Sint Maarten

8.0 out of 10, Very Good, (1)
$241 nightly
The price is $241
Dec 8 - Dec 9
Total with taxes and fees
Caribbean Sea Studio next to The Morgan Resort
TV
A117 - Lovely 2 Bedroom with Lagoon View

Apartment in Sint Maarten

2.0 star property
$347 nightly
The price is $347
Dec 15 - Dec 16
Total with taxes and fees
A117 - Lovely 2 Bedroom with Lagoon View
Pool
Beacon Hill Hideaway: Luxury Condo in Simpson Bay

Condo in Simpson Bay

$490 nightly
The price is $511
Dec 10 - Dec 11
Total with taxes and fees
Beacon Hill Hideaway: Luxury Condo in Simpson Bay
Pool
C323 – Elegant apartment with glass wall

Apartment in Sint Maarten

$288 nightly
The price is $304
Dec 8 - Dec 9
Total with taxes and fees
C323 – Elegant apartment with glass wall
Pool
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

Apartment in Simpson Bay

2.0 star property
$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)
Property grounds
Maho Beach House: Elegant 1-Bedroom, Beach Level

Condo in Simpson Bay

$282 nightly
The price is $282
Dec 7 - Dec 8
Total with taxes and fees
Maho Beach House: Elegant 1-Bedroom, Beach Level
Pool
Charming 3BR Villa w Private Pool in Pelican Key

Vacation Home in Pelican Key

$601 nightly
The price is $654
Dec 8 - Dec 9
Total with taxes and fees
Charming 3BR Villa w Private Pool in Pelican Key
Pool
A102 - Cozy Apartment with Garden

Apartment in Sint Maarten

$348 nightly
The price is $369
Dec 29 - Dec 30
Total with taxes and fees
A102 - Cozy Apartment with Garden
Property grounds
Turquoise paradise, directly ON beach, gated w underground parking!

Apartment in 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
Dec 7 - Dec 8
Total with taxes and fees
Turquoise paradise, directly ON beach, gated w underground parking!
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

The Atrium Beach Resort and Spa, an Ascend Collection Resort

The Atrium Beach Resort and Spa, an Ascend Collection Resort

10/10 Excellent
"Room was spotless, nice kitchen with everything needed. Hot shower. The restaurant was excellent. Great philly chesesteak sandwich. Good beach access. Plenty of restaurants in walking distance. On the downside, don't expect the dryers to get clothes dry. Pool isn't great for swimming laps. I didn't see a gym. All in all, a great value for the money."
BRANDON 3-night trip
Posted 1 day ago
The Atrium Beach Resort and Spa, an Ascend Collection Resort

Price trends for vacation rentals in Simpson Bay

Less expensive
More expensive
This month
Next month
September
February
$402
$424
Month
Price
January
$424
February
$448
March
$424
April
$411
May
$254
June
$279
July
$283
August
$244
September
$175
October
$198
November
$275
December
$402
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 $170 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.

Explore a world of travel with Expedia

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 top-notch restaurants and lively bars.

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

White Sands Retreat - Beachside at Beacon Hill: Visitors like this Simpson Bay vacation home rental. It is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games. 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 36 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. In the larger area, you’ll find popular places like Maho Beach and Orient Bay Beach.

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.