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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Simpson Bay vacation homes

A modern living room with a large TV, a wooden coffee table, a sofa, and a sliding glass door leading to an outdoor patio with a view of mountains.

1. C301 - Beautiful Lagoon View Apartment

C301 - Beautiful Lagoon View Apartment
Cole Bay
The price is CA $239
CA $478 total
includes taxes & fees
Oct 31 - Nov 1
C301 - Beautiful Lagoon View Apartment
A balcony with a view of a coastal city and mountains. There are two wicker chairs and a small table with a vase of flowers.

2. C344 - Lagoon view with balcony

C344 - Lagoon view with balcony
Simpson Bay
The price is CA $239
CA $478 total
includes taxes & fees
Nov 8 - Nov 9
C344 - Lagoon view with balcony
A modern living room with a large sliding glass door leading to a balcony with a scenic mountain view.

3. D442 - Apartment with balcony and lagoon view

D442 - Apartment with balcony and lagoon view
Cole Bay
The price is CA $239
CA $478 total
includes taxes & fees
Nov 1 - Nov 2
D442 - Apartment with balcony and lagoon view
A swimming pool with a view of a marina and mountains.

4. D402 - Beautiful apartment with garden and view

D402 - Beautiful apartment with garden and view
Cole Bay
The price is CA $239
CA $478 total
includes taxes & fees
Nov 4 - Nov 5
D402 - Beautiful apartment with garden and view
A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

5. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is CA $172
CA $277 total
includes taxes & fees
Nov 21 - Nov 22
Philips Scott House Calinago
A spacious living room with a sofa, armchair, and a coffee table. There is a painting on the wall and a window providing a view.

6. Quiet cozy flat in the centre of the island.

Quiet cozy flat in the centre of the island.
Weymouth Hill, Sint Maarten
7.6 out of 10, Good, (5 reviews)
"Amazing view, Very friendly and helpful people. Only 1 thing is a must that's a SUV rental car. And some driving skills. But still a great spot to be spending your holiday."
Netherlands
Tobias
The price is CA $224
CA $299 total
includes taxes & fees
Nov 1 - Nov 2
Quiet cozy flat in the centre of the island.
A covered outdoor seating area with a view of the sea, featuring a sofa, chairs, and a table.

7. 3BR Townhouse in Pelican Key w/ Pool & Beach Acess

3BR Townhouse in Pelican Key w/ Pool & Beach Acess
Pelican Key
2.0 out of 10, (1 review)
The price is CA $330
CA $857 total
includes taxes & fees
Nov 2 - Nov 3
3BR Townhouse in Pelican Key w/ Pool & Beach Acess
A covered patio with a table and chairs, surrounded by potted plants and overlooking a scenic view of hills and houses.

8. Lovely room in a nice villa , close to Friars bay and happy bay

Lovely room in a nice villa , close to Friars bay and happy bay
Saint-martin
9.0 out of 10, Wonderful, (11 reviews)
"Great place to stay. Will definitely be staying again next year! "
United States
Kurt
The price is CA $109
CA $169 total
includes taxes & fees
Nov 2 - Nov 3
Lovely room in a nice villa , close to Friars bay and happy bay
A wooden deck with a dining area, kitchen, and potted plants.

9. To complete

To complete
Cul-de-Sac
10.0 out of 10, Exceptional, (1 review)
"Jamal is very helpful, great communication."
Canada
Abdal M.
The price is CA $70
CA $78 total
includes taxes & fees
Nov 7 - Nov 8
To complete
A covered outdoor area with a pool, chairs, and a table.

10. 1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
The price is CA $206
CA $346 total
includes taxes & fees
Oct 30 - Oct 31
1-Bedroom Loft Apartment in Point Blanche
A beach with clear turquoise water, a dock with a boat, and a hotel in the background.

11. To complete

To complete
Grand Case
The price is CA $187
CA $203 total
includes taxes & fees
Nov 24 - Nov 25
To complete
A wooden deck with a dining area, kitchen, and potted plants.

12. To complete

To complete
Cul-de-Sac
The price is CA $76
CA $84 total
includes taxes & fees
Nov 2 - Nov 3
To complete
A coastal landscape with a person standing near the water's edge, vegetation in the foreground, and a hilly background.

13. To complete

To complete
Cul-de-Sac
The price is CA $86
CA $94 total
includes taxes & fees
Nov 1 - Nov 2
To complete
A wooden deck with a dining area, kitchen, and potted plants.

14. To complete

To complete
Cul-de-Sac
The price is CA $76
CA $84 total
includes taxes & fees
Nov 13 - Nov 14
To complete
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

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

10/10 Excellent
"It was my wife birthday and everyone made our first visit there welcoming and we had a wonderful time."
Adjai 5-night trip
Posted 7 hours ago
Simpson Bay Resort, Marina & Spa

Find out more about Simpson Bay

Simpson Bay Vacation Homes information

Number of reviews
1
Accommodation
32 Vacation Homes
Lowest Price
CA $78
Highest Price
CA $857