Simpson Bay Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Simpson Bay vacation rentals

Balcony
The Hills Residence

Aparthotel in Simpson Bay

The Hills Residence
3.0 star property
8.8 out of 10, Excellent, (62)
"Good location, walkable area, great views. "
United States
Tiffany
The Hills Residence
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 P9,928
P11,120 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Simpson Bay Suites
Outdoor pool, sun 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 P25,356
P28,167 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Hilton Vacation Club Royal Palm 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.
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Top Simpson Bay Hotel Reviews

La Vista Hotel

La Vista Hotel

10/10 Excellent
"Super clean, great area. Not a single complaint!"
Rebecca M 6-night trip
Posted 2 days ago
La Vista Hotel

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 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.

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.