A wooden pier extending into calm waters with sailboats anchored nearby.

Simpson Bay Holiday Rentals

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Simpson Bay holiday rentals

On the beach, sun-loungers, beach umbrellas, beach towels

1. 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, (1,262 reviews)
"Rooms were clean and staff were great"
United States
Rosaida
The price is S$237
includes taxes & fees
25 Aug - 26 Aug
Hilton Vacation Club Royal Palm St. Maarten
Terrace/patio

2. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (160 reviews)
"AC worked well the room was cleaned daily and the staff was always friendly and made great suggestions for dinning and places to see."
United States
Michael
The price is S$175
includes taxes & fees
5 Aug - 6 Aug
Simpson Bay Suites
Balcony

3. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (160 reviews)
"Comfortable room and ac was a welcome after a hot day."
United States
Maria
The price is S$346
includes taxes & fees
4 Aug - 5 Aug
The Hills Residence
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
"This is my 3rd time at Flamingo and it’s always the absolute best time ever. Consistently clean and comfy and the staff are always amazing and extremely helpful. Thank you again for an amazing vacation stay! ❤️"
Amber 6-night trip
Posted 8 hours ago
Hilton Vacation Club Flamingo Beach St. Maarten

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 46 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 Mullet 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.