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 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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 $244
CA $443 total
includes taxes & fees
Nov 15 - Nov 16
C344 - Lagoon view with balcony
An outdoor patio with a view of mountains, a sofa, chairs, and a table.

2. C301 - Beautiful Lagoon View Apartment

C301 - Beautiful Lagoon View Apartment
Cole Bay
The price is CA $244
CA $464 total
includes taxes & fees
Nov 30 - Dec 1
C301 - Beautiful Lagoon View Apartment
A modern living room with a large window, a flat-screen TV, a dining area, and a view of a coastal town.

3. C343 - Discover this charming 1-bedroom apartment

C343 - Discover this charming 1-bedroom apartment
Cole Bay
The price is CA $219
CA $416 total
includes taxes & fees
Nov 18 - Nov 19
C343 - Discover this charming 1-bedroom 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 CA $244
CA $464 total
includes taxes & fees
Dec 7 - Dec 8
D402 - Beautiful apartment with garden and view
A beach with rows of sun loungers, palm trees, and a clear view of the ocean.

5. The Luxe | Upscale 2BR Steps to Beach

The Luxe | Upscale 2BR Steps to Beach
Simpson Bay
The price is CA $280
CA $864 total
includes taxes & fees
Nov 23 - Nov 24
The Luxe | Upscale 2BR Steps to Beach
A beach with rows of sun loungers, palm trees, and a clear view of the ocean.

6. Tranquility | Luxury 2BR Steps to Beach

Tranquility | Luxury 2BR Steps to Beach
Simpson Bay
The price is CA $279
CA $864 total
includes taxes & fees
Nov 22 - Nov 23
Tranquility | Luxury 2BR Steps to Beach
A beach with rows of sun loungers, palm trees, and a clear view of the ocean.

7. Nirvana | Modern 2BR Steps to Simpson Bay Beach

Nirvana | Modern 2BR Steps to Simpson Bay Beach
Simpson Bay
The price is CA $279
CA $864 total
includes taxes & fees
Nov 22 - Nov 23
Nirvana | Modern 2BR Steps to Simpson Bay Beach
A beach with rows of sun loungers, palm trees, and a clear view of the ocean.

8. Utopia | Luxury 2BR Steps to Simpson Bay Beach

Utopia | Luxury 2BR Steps to Simpson Bay Beach
Simpson Bay
The price is CA $310
CA $897 total
includes taxes & fees
Nov 22 - Nov 23
Utopia | Luxury 2BR Steps to Simpson Bay Beach
A balcony with a view of a coastal town, a hanging chair, and a table with a vase.

9. C326 - Beautiful Apartment With Balcony

C326 - Beautiful Apartment With Balcony
Cole Bay
The price is CA $244
CA $464 total
includes taxes & fees
Dec 6 - Dec 7
C326 - Beautiful Apartment With Balcony
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 CA $196
CA $307 total
includes taxes & fees
Nov 20 - Nov 21
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.

11. 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 $110
CA $159 total
includes taxes & fees
Nov 23 - Nov 24
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.

12. 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 $294 total
includes taxes & fees
Nov 20 - Nov 21
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.

13. 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 $456
CA $968 total
includes taxes & fees
Nov 17 - Nov 18
3BR Townhouse in Pelican Key w/ Pool & Beach Acess
A coastal town with a marina, clear blue water, and mountains in the background.

14. C303 - Beautiful 1 Bedroom with Terrace

C303 - Beautiful 1 Bedroom with Terrace
Cole Bay
The price is CA $244
CA $443 total
includes taxes & fees
Nov 15 - Nov 16
C303 - Beautiful 1 Bedroom with Terrace
A modern living room with a dining area, a staircase, and a ceiling fan.

15. 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 $521
CA $701 total
includes taxes & fees
Dec 9 - Dec 10
Modern 3BR Home with Own Private Pool - Centrally Located - Quiet Neighborhood
A beach with clear water, some scattered leaves, and houses in the background.

16. To complete

To complete
Grand Case
The price is CA $189
CA $204 total
includes taxes & fees
Nov 24 - Nov 25
To complete
A wooden deck with a dining area, kitchen, and potted plants.

17. 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 22 - Nov 23
To complete
A wooden deck with a dining area, kitchen, and potted plants.

18. To complete

To complete
Cul-de-Sac
The price is CA $77
CA $85 total
includes taxes & fees
Dec 4 - Dec 5
To complete
A covered outdoor area with wooden flooring, white furniture, and a view of greenery.

19. To complete

To complete
Cul-de-Sac
The price is CA $77
CA $85 total
includes taxes & fees
Nov 19 - Nov 20
To complete
A beach scene with a sunset, boats, and people.

20. To complete

To complete
Cul-de-Sac
The price is CA $87
CA $94 total
includes taxes & fees
Nov 23 - Nov 24
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

Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

10/10 Excellent
"Great resort love it here"
Carlos 6-night trip
Posted 7 hours ago
Hilton Vacation Club Flamingo Beach St. Maarten

Find out more about Simpson Bay

Simpson Bay Vacation Homes information

Number of reviews
15
Accommodation
32 Vacation Homes
Lowest Price
CA $79
Highest Price
CA $968