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

Our top choices for Simpson Bay vacation homes

A modern living room with a large sliding glass door leading to a balcony with a scenic mountain view.

1. D442 - Apartment with balcony and lagoon view

D442 - Apartment with balcony and lagoon view
Cole Bay
The price is CA $258
CA $497 total
includes taxes & fees
Oct 25 - Oct 26
D442 - Apartment with balcony and lagoon view
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.

2. C301 – Beautiful Lagoon View Apartment

C301 – Beautiful Lagoon View Apartment
Cole Bay
The price is CA $259
CA $504 total
includes taxes & fees
Nov 4 - Nov 5
C301 – Beautiful Lagoon View Apartment
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 $343
CA $906 total
includes taxes & fees
Oct 24 - Oct 25
Utopia A3 | Beachside Stay @ The Drake Residences
A covered patio with a table and chairs, surrounded by potted plants and overlooking a scenic view of hills and houses.

4. 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 $111
CA $171 total
includes taxes & fees
Oct 22 - Oct 23
Lovely room in a nice villa , close to Friars bay and happy bay
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 $194
CA $308 total
includes taxes & fees
Nov 8 - Nov 9
Philips Scott House Calinago
A covered outdoor seating area with a view of the sea, featuring a sofa, chairs, and a table.

6. 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 $311
CA $819 total
includes taxes & fees
Oct 21 - Oct 22
3BR Townhouse in Pelican Key w/ Pool & Beach Acess
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 $226
CA $302 total
includes taxes & fees
Oct 22 - Oct 23
Quiet cozy flat in the centre of the island.
A covered outdoor area with a pool, chairs, and a table.

8. 1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
The price is CA $186
CA $321 total
includes taxes & fees
Oct 26 - Oct 27
1-Bedroom Loft Apartment in Point Blanche
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 $71
CA $79 total
includes taxes & fees
Nov 7 - Nov 8
To complete
A wooden deck with a dining area, kitchen, and potted plants.

10. To complete

To complete
Cul-de-Sac
The price is CA $78
CA $85 total
includes taxes & fees
Nov 2 - Nov 3
To complete
A wooden deck with a dining area, kitchen, and potted plants.

11. To complete

To complete
Cul-de-Sac
The price is CA $78
CA $85 total
includes taxes & fees
Oct 25 - Oct 26
To complete
A tent-style room with a bed, a wooden chair, a small table with a plant, a sink, and a mirror.

12. To complete

To complete
Cul-de-Sac
The price is CA $87
CA $95 total
includes taxes & fees
Nov 1 - Nov 2
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

The Atrium Beach Resort and Spa, an Ascend Collection Resort

The Atrium Beach Resort and Spa, an Ascend Collection Resort

10/10 Excellent
"Great time"
Jaszmin 3-night trip
Posted 13 hours ago
The Atrium Beach Resort and Spa, an Ascend Collection Resort

Find out more about Simpson Bay

Simpson Bay Vacation Homes information

Number of reviews
1
Accommodation
36 Vacation Homes
Lowest Price
CA $79
Highest Price
CA $906