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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Simpson Bay holiday 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
C344 - Lagoon view with balcony
A bedroom with a bed, nightstands, a wall-mounted artwork, and a door.

2. D402 - Beautiful apartment with garden and view

D402 - Beautiful apartment with garden and view
Cole Bay
D402 - Beautiful apartment with garden and view
A covered patio with a table and chairs, surrounded by potted plants and overlooking a scenic view of hills and houses.

3. 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 £96
includes taxes & fees
29 Oct - 30 Oct
Lovely room in a nice villa , close to Friars bay and happy bay
A modern living room with a flat-screen TV, a sofa, a coffee table, and a staircase.

4. 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 £359
includes taxes & fees
1 Oct - 2 Oct
Modern 3BR Home with Own Private Pool - Centrally Located - Quiet Neighborhood
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 £163
includes taxes & fees
31 Oct - 1 Nov
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 £460
includes taxes & fees
1 Oct - 2 Oct
3BR Townhouse in Pelican Key w/ Pool & Beach Acess
A covered outdoor area with a pool, chairs, and a table.

7. 1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
The price is £146
includes taxes & fees
30 Oct - 31 Oct
1-Bedroom Loft Apartment in Point Blanche
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.

8. 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 £161
includes taxes & fees
2 Oct - 3 Oct
Quiet cozy flat in the centre of the island.
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 £43
includes taxes & fees
9 Oct - 10 Oct
To complete
A beach with clear water, some scattered leaves, and houses in the background.

10. To complete

To complete
Grand Case
The price is £91
includes taxes & fees
4 Oct - 5 Oct
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 £51
includes taxes & fees
31 Oct - 1 Nov
To complete
A wooden deck with a dining area, kitchen, and potted plants.

12. To complete

To complete
Cul-de-Sac
The price is £46
includes taxes & fees
24 Oct - 25 Oct
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 Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

8/10 Good
"The staff was very friendly"
Carmelle, 4-night trip
Posted 6 hours ago
Hilton Vacation Club Royal Palm St. Maarten

Find out more about Simpson Bay

Simpson Bay Holiday Homes information

Number of reviews
15
Accommodation
36 Holiday Homes
Lowest Price
£43
Highest Price
£460