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

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Simpson Bay holiday rentals

Terrace/patio

Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (159 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 3.195.086 ₫
3.578.759 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Simpson Bay Suites
Amazing Top Floor Apartment | Balcony

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (154 reviews)
"We had a great stay definitely will be back!!"
United States
Lornella
The price is 4.454.422 ₫
7.483.428 ₫ total
includes taxes & fees
6 Jul - 7 Jul
The Hills Residence
On the beach, sun-loungers, beach umbrellas, beach towels

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, (1,249 reviews)
"Great staff.. Great location..Great property"
United States
Wilbert
The price is 3.408.880 ₫
4.269.620 ₫ total
includes taxes & fees
18 Jul - 19 Jul
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

Baker's Suites

Baker's Suites

10/10 Excellent
"Great staff, nice and clean unit. Great location, no complaints"
Jade 5-night trip
Posted 1 hour ago
Baker's Suites

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. 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.