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

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Simpson Bay vacation homes

Deluxe Apartment, Courtyard View | Blackout drapes, WiFi (free)

1. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
The price is ￥24,082
￥36,768 total
includes taxes & fees
Aug 4 - Aug 5
Philips Scott House Calinago
Outdoor dining

2. 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 ￥11,794
￥15,060 total
includes taxes & fees
Aug 11 - Aug 12
Lovely room in a nice villa , close to Friars bay and happy bay
Living area

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 ￥25,184
￥34,156 total
includes taxes & fees
Aug 5 - Aug 6
Quiet cozy flat in the centre of the island.
Outdoor dining

4. 1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
The price is ￥13,458
￥25,419 total
includes taxes & fees
Sep 2 - Sep 3
1-Bedroom Loft Apartment in Point Blanche
Property grounds

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 ￥40,106
￥97,618 total
includes taxes & fees
Aug 4 - Aug 5
3BR Townhouse in Pelican Key w/ Pool & Beach Acess
Property grounds

6. Apartment: Beach and Airport Within Walking Distance

Apartment: Beach and Airport Within Walking Distance
Grand Case
The price is ￥23,587
￥23,587 total
includes taxes & fees
Aug 8 - Aug 9
Apartment: Beach and Airport Within Walking Distance
Beach

7. To complete

To complete
Grand Case
The price is ￥17,418
￥19,232 total
includes taxes & fees
Aug 4 - Aug 5
To complete
Outdoor dining

8. To complete

To complete
Cul-de-Sac
The price is ￥8,165
￥9,072 total
includes taxes & fees
Aug 4 - Aug 5
To complete
Beach

9. To complete

To complete
Cul-de-Sac
The price is ￥9,979
￥10,886 total
includes taxes & fees
Aug 4 - Aug 5
To complete
Outdoor dining

10. To complete

To complete
Cul-de-Sac
The price is ￥8,891
￥9,798 total
includes taxes & fees
Aug 4 - Aug 5
To complete
Outdoor dining

11. To complete

To complete
Cul-de-Sac
The price is ￥8,891
￥9,798 total
includes taxes & fees
Aug 4 - Aug 5
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

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

10/10 Excellent
"Had an absolutely amazing time. Shout out to Ziggy from the lobby pool bar and the amazing staff for all they did to make my stay special. I will be back 😀."
duane 4-night trip
Posted 7 hours ago
Simpson Bay Resort, Marina & Spa

Find out more about Simpson Bay

Simpson Bay Vacation Homes information

Number of reviews
Accommodation
31 Vacation Homes
Lowest Price
￥9,072
Highest Price
￥97,618