Holiday houses in Simpson Bay
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Top-rated holiday rentals in Simpson Bay
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Simpson Bay holiday rentals
Other great holiday rentals in Simpson Bay
Guest favourite
Condo in Simpson Bay
4.96 out of 5 average rating, 72 reviewsFive Star Luxury Beachfront Condo Private Hot Tub
3 – 10 Nov
$5,486 AUD total
Guest favourite
Apartment in Simpson Bay
5.0 out of 5 average rating, 45 reviewsHARMONY HAVEN on Simpson Bay Beach Beacon Hill
21 – 28 May
$7,605 AUD total
Guest favourite
Home in Simpson Bay
5.0 out of 5 average rating, 68 reviewsVilla Blue View .. stunning views of endless sea!
27 Sept – 4 Oct
$9,017 AUD total
Superhost
Apartment in Simpson Bay
5.0 out of 5 average rating, 3 reviewsThe Loft at Simpson Bay Yacht Club
14 – 21 Aug
$1,817 AUD total
Guest favourite
Apartment in Lowlands
5.0 out of 5 average rating, 16 reviewsRock Star Gem in Maho
23 – 30 Oct
$1,127 AUD total
Guest favourite
Apartment in Lowlands, Sint Maarten
4.83 out of 5 average rating, 18 reviewsThe Emerald at Maho
13 – 20 Aug
$1,012 AUD total
Guest favourite
Condo in Simpson Bay
5.0 out of 5 average rating, 13 reviewsPopular Beachfront Property Barefoot /Simpson bay
12 – 19 Oct
$4,558 AUD total
Guest favourite
Condo in Simpson Bay, Sint Maarten
5.0 out of 5 average rating, 28 reviewsOCEAN FRONT Steps From BEACH!
8 – 15 Jan
$5,662 AUD total
Quick stats about holiday rentals in Simpson Bay
Total rentals
320 properties
Rentals with a pool
200 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
140 properties are a good fit for families
Total number of reviews
8.2K reviews
Nightly prices starting at
$45 AUD before taxes and fees
Destinations to explore
- Orient Bay Holiday rentals
- Grand Case Holiday rentals
- Gustavia Holiday rentals
- Philipsburg Holiday rentals
- Bakers Bay Accommodation & holiday rentals
- Baie Nettlé Accommodation & holiday rentals
- Maho Beach Holiday rentals
- Marigot Accommodation & holiday rentals
- Cul-de-Sac Accommodation & holiday rentals
- Mont Vernon Accommodation & holiday rentals
- Anse Marcel Holiday rentals
- San Juan Holiday rentals
- Rentals with outdoor seating Simpson Bay
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- Monthly Rentals Simpson Bay
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