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 homes

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.

1. C344 - Lagoon view with balcony

C344 - Lagoon view with balcony
Simpson Bay
The price is CA $260
CA $504 total
includes taxes & fees
Oct 6 - Oct 7
C344 - Lagoon view with balcony
A modern living room with a large sliding glass door leading to a balcony with a scenic mountain view.

2. D442 - Apartment with balcony and lagoon view

D442 - Apartment with balcony and lagoon view
Cole Bay
The price is CA $261
CA $502 total
includes taxes & fees
Oct 28 - Oct 29
D442 - Apartment with balcony and lagoon view
A coastal scene with two large yachts on the water, palm trees, and a building with a balcony.

3. Utopia A3 | Beachside Stay @ The Drake Residences

Utopia A3 | Beachside Stay @ The Drake Residences
Simpson Bay
The price is CA $356
CA $1,108 total
includes taxes & fees
Oct 6 - Oct 7
Utopia A3 | Beachside Stay @ The Drake Residences
A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

4. 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 $192
CA $306 total
includes taxes & fees
Oct 21 - Oct 22
Philips Scott House Calinago
A covered outdoor seating area with a view of the sea, featuring a sofa, chairs, and a table.

5. 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 $314
CA $821 total
includes taxes & fees
Oct 6 - Oct 7
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.

6. 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 $112
CA $173 total
includes taxes & fees
Oct 6 - Oct 7
Lovely room in a nice villa , close to Friars bay and happy bay
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.

7. 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 $228
CA $306 total
includes taxes & fees
Oct 6 - Oct 7
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.

8. 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 traveller
The price is CA $462
CA $663 total
includes taxes & fees
Oct 6 - Oct 7
Modern 3BR Home with Own Private Pool - Centrally Located - Quiet Neighborhood
A beach with clear water, some scattered leaves, and houses in the background.

9. To complete

To complete
Grand Case
The price is CA $154
CA $170 total
includes taxes & fees
Oct 11 - Oct 12
To complete
A wooden deck with a dining area, kitchen, and potted plants.

10. 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 $72
CA $80 total
includes taxes & fees
Oct 24 - Oct 25
To complete
A coastal landscape with a person standing near the water's edge, vegetation in the foreground, and a hilly background.

11. To complete

To complete
Cul-de-Sac
The price is CA $88
CA $96 total
includes taxes & fees
Oct 15 - Oct 16
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

Baker's Suites

Baker's Suites

10/10 Excellent
"My stay was absolutely amazing. The accommodation was pristine. The staff were very friendly and helpful. Alexia, Shanae, Latoya were very friendly. Also Ms Christene our housekeeper is such a sweetheart. They suggested points of interest we could go and how to get there. Whenever we ordered breakfast they brought to our room. Love it there and will definitely stay again when we visit Sint Maarten. Thank you so much for accommodating us."
Vilma 5-night trip
Posted 1 hour ago
Baker's Suites

Find out more about Simpson Bay

Simpson Bay Vacation Homes information

Number of reviews
15
Accommodation
36 Vacation Homes
Lowest Price
CA $80
Highest Price
CA $1,108