Photo by Dorothy Schmidt

Simpson Bay Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Simpson Bay holiday rentals

Balcony
The Hills Residence

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.6 out of 10, Excellent, (60)
"Enjoyed my stay "
United States
Shakia
The Hills Residence
Outdoor pool, pool loungers
Hilton Vacation Club Royal Palm St. Maarten

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
The price is RM1,551
RM1,735 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hilton Vacation Club Royal Palm St. Maarten
Exterior
FLAMINGO BEACH

FLAMINGO BEACH

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

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
The price is RM685
RM767 total
includes taxes & fees
4 Jan - 5 Jan 2026
Simpson Bay Suites
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Simpson Bay Hotel Reviews

The Morgan Resort Spa Village

The Morgan Resort Spa Village

10/10 Excellent
"Beautiful, upscale resort and spa "
Kevin 4-night trip
Posted 16 hours ago
The Morgan Resort Spa Village

Find out more about Simpson Bay

Search for holiday rentals in Simpson Bay on Expedia.co.uk! 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.

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.