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, Sint Maarten
5.0 out of 5 average rating, 56 reviewsBeach front luxury! Huge 2BR that has it all! 😍🤩😍
24–31 Aug
$1,197 NZD per night
Guest favourite
Guesthouse in Simpson Bay
4.96 out of 5 average rating, 96 reviewsSimpson Bay Beach Apartment. Topdeck. Ocean View
18–25 May
$242 NZD per night
Guest favourite
Home in Simpson Bay
5.0 out of 5 average rating, 68 reviewsVilla Blue View .. stunning views of endless sea!
29 Jun – 6 Jul
$1,351 NZD per night
Guest favourite
Condo in Lowlands
4.94 out of 5 average rating, 88 reviewsSint Maarten La Terrasse Maho
31 May – 7 Jun
$234 NZD per night
Guest favourite
Villa in Simpson Bay, Sint Maarten
4.98 out of 5 average rating, 41 reviewsWaterfront "BONJOUR" Beacon Hill St Maarten
13–20 Oct
$1,757 NZD per night
Guest favourite
Apartment in Cupecoy
5.0 out of 5 average rating, 6 reviewsBright Studio by Mullet Beach
1–8 Sep
$170 NZD per night
Guest favourite
Apartment in Simpson Bay
5.0 out of 5 average rating, 45 reviewsHARMONY HAVEN on Simpson Bay Beach Beacon Hill
11–18 May
$1,209 NZD per night
Superhost
Condo in Simpson Bay, Sint Maarten
4.97 out of 5 average rating, 35 reviewsHamaka condo, a beachfront retreat on Simpson Bay
17–24 Sep
$400 NZD per night
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
$51 NZD before taxes and fees
Destinations to explore
- Orient Bay Holiday rentals
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- Baie Nettlé Holiday rentals
- Maho Beach Holiday rentals
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- Rentals with pools Simpson Bay
- Family-friendly rentals Simpson Bay
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