Simpson Bay Holiday Rentals

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Check prices for these dates

Tonight
18 Dec - 19 Dec
Tomorrow
19 Dec - 20 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Simpson Bay holiday rentals

Balcony
The Hills Residence

Aparthotel in Simpson Bay

The Hills Residence
3.0 star property
9.0 out of 10, Wonderful, (54)
"Enjoyed my stay "
United States
Shakia
The Hills Residence
On the beach, sun-loungers, beach umbrellas, beach towels
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, (1160)
"One of my favorite places to stay."
United States
Carlos
The price is S$449
includes taxes & fees
13 Jan - 14 Jan, 2026
Hilton Vacation Club Royal Palm St. Maarten
Beach nearby, white sand, sun-loungers, beach umbrellas
Simpson Bay Suites

Aparthotel in Simpson Bay

Simpson Bay Suites
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
The price is S$220
includes taxes & fees
19 Dec - 20 Dec
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.
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Top Simpson Bay Hotel Reviews

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

10/10 Excellent
"Perfect environment. Wonderful professional staff. "
Colin 1-night trip
Posted 3 days ago
The Villas at Simpson Bay Resort

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 40 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. In the wider area, you’ll find popular places such as Maho Beach and Orient Bay Beach.

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.