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

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Simpson Bay holiday 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, (1,322 reviews)
"The staff was very friendly"
United States
Carmelle,
The price is ฿5,398
฿6,508 total
includes taxes & fees
5 Nov - 6 Nov
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, (168 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is ฿4,536
฿5,080 total
includes taxes & fees
25 Oct - 26 Oct
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, (172 reviews)
"Very good"
United States
Alyssia
The price is ฿7,168
฿12,550 total
includes taxes & fees
6 Nov - 7 Nov
The Hills Residence
A hotel room with a bed, a sofa, a small round table, and a chair. There is a bathroom visible through an open door.

4. July Apartments

July Apartments
3.0 star property
Madame's Estate
9.0 out of 10, Wonderful, (254 reviews)
"The property was no frills and the staff super helpful. Would stay again!"
United States
JoyAnn Carolyn
The price is ฿3,599
฿3,779 total
includes taxes & fees
24 Oct - 25 Oct
July Apartments
A modern living room with large windows, a purple sofa, and a view of the beach and ocean.

5. Mullet Bay Suites: Your Luxury Stay Awaits

Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
Maho
9.6 out of 10, Exceptional, (185 reviews)
"This place was amazing. Perfect experience"
United States
Kenneth
The price is ฿8,602
฿12,064 total
includes taxes & fees
30 Oct - 31 Oct
Mullet Bay Suites: Your Luxury Stay Awaits
A view from inside a building looking out to a beach with clear turquoise water and a distant ship.

6. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.6 out of 10, Good, (75 reviews)
"The place was amazing"
United States
brenton
The price is ฿2,450
฿2,939 total
includes taxes & fees
25 Oct - 26 Oct
MIDTOWN MOTEL SXM
A swimming pool with clear water, a grassy area, and a view of a coastal landscape with buildings.

7. condostmaarten by the sea -Adults Only-

condostmaarten by the sea -Adults Only-
4.0 star property
Indigo Bay
9.2 out of 10, Wonderful, (43 reviews)
"Love love the property was amazing. Will definitely return."
United States
Muneca
The price is ฿11,592
฿16,733 total
includes taxes & fees
28 Oct - 29 Oct
condostmaarten by the sea -Adults Only-
A large swimming pool surrounded by palm trees and lounge chairs, with a hotel building in the background.

8. Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten
4.0 star property
Oyster Pond
8.8 out of 10, Excellent, (33 reviews)
"Large rooms with great ocean views! Helpful staff and good beach access!"
United States
Gavin
The price is ฿21,138
฿25,366 total
includes taxes & fees
26 Oct - 27 Oct
Dawn Beach Club Resort Sint Maarten
Outdoor dining

9. 4bed Condo - Sleeps 8 - Pool, Bbq, Views, Parking

4bed Condo - Sleeps 8 - Pool, Bbq, Views, Parking
3.5 star property
St. Peters
The price is ฿17,893
฿21,471 total
includes taxes & fees
1 Nov - 2 Nov
4bed Condo - Sleeps 8 - Pool, Bbq, Views, Parking
A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

10. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is ฿5,141
฿7,849 total
includes taxes & fees
30 Oct - 31 Oct
Philips Scott House Calinago
A multi-story hotel with a pool, set against a mountainous backdrop.

11. Singh Luxury Apartments With sea View, Apt.1

Singh Luxury Apartments With sea View, Apt.1
3.0 star property
Oyster Pond
The price is ฿10,848
฿13,911 total
includes taxes & fees
25 Oct - 26 Oct
Singh Luxury Apartments With sea View, Apt.1
A rooftop terrace with a pool, lounge chairs, and a table with a drink.

12. Avenue du lagon

Avenue du lagon
Oyster Pond
The price is ฿48,721
฿65,791 total
includes taxes & fees
18 Nov - 19 Nov
Avenue du lagon
A multi-story hotel with a pool, set against a mountainous backdrop.

13. Singh Luxury Apartments With sea View, Apt.3

Singh Luxury Apartments With sea View, Apt.3
3.0 star property
Oyster Pond
2.0 out of 10, (1 review)
The price is ฿23,873
฿27,586 total
includes taxes & fees
24 Oct - 25 Oct
Singh Luxury Apartments With sea View, Apt.3
A multi-story building with a pool, surrounded by hilly terrain.

14. Singh Luxury Apartments With sea View, Apt.2

Singh Luxury Apartments With sea View, Apt.2
3.5 star property
Oyster Pond
The price is ฿10,848
฿13,911 total
includes taxes & fees
25 Oct - 26 Oct
Singh Luxury Apartments With sea View, Apt.2
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 was great property to stay at, near the everything and staff is very helpful"
Kimberley 4-night trip
Posted 6 hours ago
Hilton Vacation Club Flamingo Beach St. Maarten

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
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  • 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 top-notch restaurants and lively bars.

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

Philips Scott House Calinago: This holiday 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 such as a microwave and free parking are also available for your convenience.

How many holiday rentals are there in Simpson Bay?

With 38 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. Hollywood Casino and Simpson Bay Beach 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.