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

Holiday Homes in Simpson Bay

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Check prices for these dates

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

Our top choices for Simpson Bay holiday 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
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 €321
includes taxes & fees
4 Nov - 5 Nov
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 €599
includes taxes & fees
23 Oct - 24 Oct
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 €112
includes taxes & fees
22 Oct - 23 Oct
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 €208
includes taxes & fees
22 Oct - 23 Oct
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 €529
includes taxes & fees
2 Nov - 3 Nov
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 €192
includes taxes & fees
2 Nov - 3 Nov
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
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.
To complete
A wooden deck with a dining area, kitchen, and potted plants.

10. To complete

To complete
Cul-de-Sac
To complete
A wooden deck with a dining area, kitchen, and potted plants.

11. To complete

To complete
Cul-de-Sac
To complete
A coastal landscape with a person standing near the water's edge, vegetation in the foreground, and a hilly background.

12. To complete

To complete
Cul-de-Sac
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

Cocovaa

Cocovaa

10/10 Excellent
"My experience at this hotel was nothing short of amazing! From the moment I arrived, everything exceeded my expectations. The hotel was beautiful, clean, comfortable, and welcoming. The staff was exceptionally friendly, professional, and attentive, making sure every detail was taken care of and that I felt valued throughout my stay."
Jaclyn Petrin 3-night trip
Posted 4 hours ago
Cocovaa

Find out more about Simpson Bay

Simpson Bay Holiday Homes information

Number of reviews
1
Accommodation
36 Holiday Homes
Lowest Price
€112
Highest Price
€599