Simpson Bay Holiday Rentals

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Check prices for these dates

Tonight
28 Dec - 29 Dec
Tomorrow
29 Dec - 30 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Simpson Bay holiday rentals

Balcony
The Hills Residence

Aparthotel in Simpson Bay

The Hills Residence
3.0 star property
8.8 out of 10, Excellent, (58)
"Enjoyed my stay "
United States
Shakia
The Hills Residence
Outdoor pool, pool loungers
Hilton Vacation Club Royal Palm St. Maarten

Aparthotel in Simpson Bay

Hilton Vacation Club Royal Palm St. Maarten
4.0 star property
9.0 out of 10, Wonderful, (1166)
"Room was great, resort was great, staff was great"
Canada
Gisele
The price is HK$2,977
HK$3,330 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hilton Vacation Club Royal Palm St. Maarten
Exterior
FLAMINGO BEACH

Aparthotel in Pelican Key

FLAMINGO BEACH
3.5 star property
FLAMINGO BEACH
Beach nearby, white sand, sun-loungers, beach umbrellas
Simpson Bay Suites

Aparthotel in Simpson Bay

Simpson Bay Suites
3.5 star property
7.0 out of 10, Good, (127)
"No issues. Staff were very welcoming and accommodating. Was a pleasant stay. "
United States
Sharmain
The price is HK$1,313
HK$1,471 total
includes taxes & fees
4 Jan - 5 Jan 2026
Simpson Bay Suites
Pool
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

Apartment in Simpson Bay

1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
10.0 out of 10, Exceptional, (2)
"perfect!!"
United States
jason l.
The price is HK$1,564
HK$2,505 total
includes taxes & fees
29 Dec - 30 Dec
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Pool
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

Apartment in Simpson Bay

Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
2.0 star property
The price is HK$1,787
HK$2,802 total
includes taxes & fees
5 Jan - 6 Jan 2026
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
Interior
B226 - Amazing Lagoon View with Balcony

Apartment in Sint Maarten

B226 - Amazing Lagoon View with Balcony
The price is HK$1,834
HK$2,869 total
includes taxes & fees
9 Jan - 10 Jan 2026
B226 - Amazing Lagoon View with Balcony
Pool
B254 - Cozy Apartment in the Heart of Simpson Bay

Apartment in Sint Maarten

B254 - Cozy Apartment in the Heart of Simpson Bay
B254 - Cozy Apartment in the Heart of Simpson Bay
TV
C337 - Charming 2-Bedroom Lagoon View

Apartment in Sint Maarten

C337 - Charming 2-Bedroom Lagoon View
2.0 star property
The price is HK$2,293
HK$3,525 total
includes taxes & fees
3 Jan - 4 Jan 2026
C337 - Charming 2-Bedroom Lagoon View
Pool
C302 – Modern Comfort with Private Terrace

Apartment in Simpson Bay

C302 – Modern Comfort with Private Terrace
2.0 star property
The price is HK$1,834
HK$2,854 total
includes taxes & fees
29 Dec - 30 Dec
C302 – Modern Comfort with Private Terrace
Interior
D414 – 1-Bedroom Apartment with Balcony

Apartment in Sint Maarten

D414 – 1-Bedroom Apartment with Balcony
2.0 star property
The price is HK$1,834
HK$2,751 total
includes taxes & fees
29 Dec - 30 Dec
D414 – 1-Bedroom Apartment with Balcony
Smart TV, stereo, offices
Marina Views in the Heart of Simpson Bay

Apartment in Simpson Bay

Marina Views in the Heart of 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.
The price is HK$2,518
HK$4,185 total
includes taxes & fees
21 Jan - 22 Jan 2026
Marina Views in the Heart of Simpson Bay
Property grounds
Turquoise paradise, directly ON beach, gated w underground parking!

Apartment in Simpson Bay

Turquoise paradise, directly ON beach, gated w underground parking!
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.
The price is HK$3,847
HK$4,911 total
includes taxes & fees
2 Jan - 3 Jan 2026
Turquoise paradise, directly ON beach, gated w underground parking!
Pool
C316 - Lagoon view with balcony

Holiday Home in Simpson Bay

C316 - Lagoon view with balcony
The price is HK$1,834
HK$2,893 total
includes taxes & fees
11 Jan - 12 Jan 2026
C316 - Lagoon view with balcony
Pool
D408 – Chic & Stylish 2 Bedroom with Terrace

Apartment in Sint Maarten

D408 – Chic & Stylish 2 Bedroom with Terrace
2.0 star property
The price is HK$2,293
HK$3,540 total
includes taxes & fees
16 Jan - 17 Jan 2026
D408 – Chic & Stylish 2 Bedroom with Terrace
Living area
D426 - Beautiful view of the lagoon with balcony

Holiday Home in Simpson Bay

D426 - Beautiful view of the lagoon with balcony
2.0 star property
D426 - Beautiful view of the lagoon with balcony
Pool
A102 - Cozy Apartment with Garden

Apartment in Sint Maarten

A102 - Cozy Apartment with Garden
A102 - Cozy Apartment with Garden
Pool
A116 - Immersive Simpson Bay Lagoon View

Apartment in Sint Maarten

A116 - Immersive Simpson Bay Lagoon View
A116 - Immersive Simpson Bay Lagoon View
A heated pool
A101 - Outstanding Lagoon View & Garden

Apartment in Sint Maarten

A101 - Outstanding Lagoon View & Garden
A101 - Outstanding Lagoon View & Garden
Pool
Sunny Days at Simpson Bay Yacht Club

Condo in Simpson Bay

Sunny Days at Simpson Bay Yacht Club
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.
The price is HK$5,860
HK$8,302 total
includes taxes & fees
16 Jan - 17 Jan 2026
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

Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

10/10 Excellent
"Absolutely loved our stay at this resort! We had a beach front room right one level 1. Easy access to the restaurant and beach! The staff were all very friendly! Devon at the pelican restaurant! He took care of us the entire stay. Great service, clean rooms, beautiful property, nice location. Felt extremely safe. "
Retta 5-night trip
Posted 1 day ago
Hilton Vacation Club Flamingo Beach St. Maarten

Find out more about Simpson Bay

Search for holiday rentals in Simpson Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Simpson Bay using one of the methods below:

  • View our selection of featured holiday rentals in Simpson Bay
  • Use the map to find apartments and other holiday homes in the Simpson Bay neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Simpson Bay while they last

Look no further and take a look at our great range of rental properties in Simpson Bay!

Frequently asked questions

Can I find a holiday rental in Simpson Bay?

Yes, there are holiday rentals close to the most popular sights in Simpson Bay, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Simpson Bay has to offer?

Caribbean Sea Studio next to The Morgan Resort: This highly rated holiday home rental in Simpson Bay 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 1 hot tub. Other favourite 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 holiday rentals are there in Simpson Bay?

With 41 Expedia holiday rentals, you're guaranteed 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 holiday rental in Simpson Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Simpson Bay. Holiday rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.