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

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Simpson Bay vacation homes

A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

1. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is ￥22,955
￥35,552 total
includes taxes & fees
Oct 1 - Oct 2
Philips Scott House Calinago
A modern living room with a sofa, a coffee table, a TV, and a staircase.

2. 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 traveler
The price is ￥50,417
￥72,639 total
includes taxes & fees
Sep 21 - Sep 22
Modern 3BR Home with Own Private Pool - Centrally Located - Quiet Neighborhood
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.

3. 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 ￥24,821
￥33,663 total
includes taxes & fees
Sep 30 - Oct 1
Quiet cozy flat in the centre of the island.
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 ￥12,531
￥19,333 total
includes taxes & fees
Sep 21 - Sep 22
Lovely room in a nice villa , close to Friars bay and happy bay
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 ￥53,079
￥112,430 total
includes taxes & fees
Sep 23 - Sep 24
3BR Townhouse in Pelican Key w/ Pool & Beach Acess
A covered outdoor area with a pool, chairs, and a table.

6. 1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
The price is ￥13,534
￥25,341 total
includes taxes & fees
Sep 26 - Sep 27
1-Bedroom Loft Apartment in Point Blanche
A compact kitchen with a refrigerator, stove, and microwave. There is a painting on the wall and a ceiling fan.

7. To complete

To complete
Grand Case
The price is ￥17,185
￥18,975 total
includes taxes & fees
Sep 30 - Oct 1
To complete
A wooden deck with a dining area, kitchen, and potted plants.

8. To complete

To complete
Cul-de-Sac
The price is ￥8,055
￥8,950 total
includes taxes & fees
Sep 30 - Oct 1
To complete
A coastal landscape with a person standing near the water's edge, vegetation in the foreground, and a hilly background.

9. To complete

To complete
Cul-de-Sac
The price is ￥9,846
￥10,741 total
includes taxes & fees
Sep 19 - Sep 20
To complete
A wooden deck with a dining area, kitchen, and potted plants.

10. To complete

To complete
Cul-de-Sac
The price is ￥8,771
￥9,666 total
includes taxes & fees
Oct 2 - Oct 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 ￥8,771
￥9,666 total
includes taxes & fees
Sep 19 - Sep 20
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 Morgan Resort Spa Village

The Morgan Resort Spa Village

10/10 Excellent
"Room was great! Pool even better!!"
jamie 4-night trip
Posted 12 hours ago
The Morgan Resort Spa Village

Find out more about Simpson Bay

Simpson Bay Vacation Homes information

Number of reviews
14
Accommodation
36 Vacation Homes
Lowest Price
￥8,950
Highest Price
￥112,430