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

Simpson Bay Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Simpson Bay vacation rentals

A resort with a view of sailboats on the water, a beach with palm trees, and a modern building with balconies.

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, (1,308 reviews)
"The property was very conveniently located. The rooms were exactly like the pictures and the staff were very lovely."
United States
Erika
The price is P6,850
P8,833 total
includes taxes & fees
Oct 11 - Oct 12
Hilton Vacation Club Royal Palm St. Maarten
A high-rise hotel with a view of the sunset over a marina.

2. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (165 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is P7,591
P8,502 total
includes taxes & fees
Sep 29 - Sep 30
Simpson Bay Suites
A modern living room with a large sliding glass door leading to a balcony with a view of a coastal town and mountains.

3. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (170 reviews)
"Very good"
United States
Alyssia
The price is P10,583
P17,779 total
includes taxes & fees
Oct 4 - Oct 5
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

Mary's Boon Beach Resort & Spa

Mary's Boon Beach Resort & Spa

10/10 Excellent
"This is a hidden gem in Saint Maarten! A small cozy resort. Nothing like the large resorts. The staff, beach, food, and drinks were excellent. We would definitely come back. It is close to the airport so you’ll hear all the planes and it is not walking distance to the restaurants in Simpson Bay."
Robert 1-night trip
Posted 1 day ago
Mary's Boon Beach Resort & Spa

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 top-notch restaurants and lively bars.

What are some of the best vacation home rentals that Simpson Bay has to offer?

Philips Scott House Calinago: This vacation home rental outside of Simpson Bay is in a shopping district and equipped with air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Amenities like a microwave and free parking are also available for your convenience.

How many vacation rentals are there in Simpson Bay?

With 38 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.