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

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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 window offering a view of a coastal town and mountains.

1. D417 - One Bedroom Apartment with Lagoon View

D417 - One Bedroom Apartment with Lagoon View
Cole Bay
D417 - One Bedroom Apartment with Lagoon View
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 ￥26,959
￥51,127 total
includes taxes & fees
Nov 8 - Nov 9
C344 - Lagoon view with balcony
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.

3. C301 - Beautiful Lagoon View Apartment

C301 - Beautiful Lagoon View Apartment
Cole Bay
The price is ￥26,959
￥51,127 total
includes taxes & fees
Nov 4 - Nov 5
C301 - Beautiful Lagoon View Apartment
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 ￥26,959
￥51,127 total
includes taxes & fees
Nov 5 - Nov 6
D402 - Beautiful apartment with garden and view
A modern living room with a large sliding glass door leading to a balcony with a scenic mountain view.

5. D442 - Apartment with balcony and lagoon view

D442 - Apartment with balcony and lagoon view
Cole Bay
D442 - Apartment with balcony and lagoon view
A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

6. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is ￥21,696
￥33,913 total
includes taxes & fees
Nov 2 - Nov 3
Philips Scott House Calinago
A covered patio with a table and chairs, surrounded by potted plants and overlooking a scenic view of hills and houses.

7. 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 ￥12,308
￥17,759 total
includes taxes & fees
Nov 2 - Nov 3
Lovely room in a nice villa , close to Friars bay and happy bay
A covered outdoor seating area with a view of the sea, featuring a sofa, chairs, and a table.

8. 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 ￥37,033
￥92,789 total
includes taxes & fees
Nov 2 - Nov 3
3BR Townhouse in Pelican Key w/ Pool & Beach Acess
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.
To complete
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.

10. 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 ￥25,210
￥32,615 total
includes taxes & fees
Nov 4 - Nov 5
Quiet cozy flat in the centre of the island.
A modern living room with a flat-screen TV, a sofa, a coffee table, and a staircase.

11. Modern 3BR Home with Own Private Pool - Centrally Located - Quiet Neighborhood

Modern 3BR Home with Own Private Pool - Centrally Located - Quiet Neighborhood
Cole bay
9.8 out of 10, Exceptional, (14 reviews)
"Private pool was definitely a plus for the heat and close to all the action"
United States
Anonymous traveler
The price is ￥51,207
￥69,996 total
includes taxes & fees
Nov 4 - Nov 5
Modern 3BR Home with Own Private Pool - Centrally Located - Quiet Neighborhood
A compact kitchen with a refrigerator, stove, and microwave. There is a painting on the wall and a ceiling fan.

12. To complete

To complete
Grand Case
The price is ￥21,099
￥22,857 total
includes taxes & fees
Nov 24 - Nov 25
To complete
A covered outdoor area with a pool, chairs, and a table.

13. 1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
The price is ￥23,319
￥37,241 total
includes taxes & fees
Nov 2 - Nov 3
1-Bedroom Loft Apartment in Point Blanche
A wooden deck with a dining area, kitchen, and potted plants.

14. To complete

To complete
Cul-de-Sac
The price is ￥8,616
￥9,495 total
includes taxes & fees
Nov 2 - Nov 3
To complete
A tent-style room with a bed, a wooden chair, a small table with a plant, a sink, and a mirror.

15. To complete

To complete
Cul-de-Sac
The price is ￥9,671
￥10,550 total
includes taxes & fees
Nov 2 - Nov 3
To complete
A wooden deck with a dining area, kitchen, and potted plants.

16. To complete

To complete
Cul-de-Sac
The price is ￥8,616
￥9,495 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

Azure Hotel and Art Studio

Azure Hotel and Art Studio

10/10 Excellent
"A perfect relaxing place for a Nice short weekend get away. Back door lead straight to the beach chairs w/ umbrella."
Tu 3-night trip
Posted 2 hours ago
Azure Hotel and Art Studio

Find out more about Simpson Bay

Simpson Bay Vacation Homes information

Number of reviews
15
Accommodation
32 Vacation Homes
Lowest Price
￥9,495
Highest Price
￥92,789