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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Apartment in Simpson Bay, Sint Maarten
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 beds, 3 private bathrooms
9–14 Aug
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4.92 out of 5 average rating, 24 reviews
Top guest favourite
Villa in Philipsburg, Sint Maarten
Villa Dream View Belair Sint Maarten SXM
4.99 out of 5 average rating, 328 reviews, 3 bedrooms, 4 beds, 3 bathrooms
21–26 Sept
Top guest favourite
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
5.0 out of 5 average rating, 39 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
6–11 Jul
Guest favourite
Home in Cole Bay, Sint Maarten
Spacious 3BR with Private Cozy Pool
5.0 out of 5 average rating, 55 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
5.0 out of 5 average rating, 76 reviews, 2 beds, 1.5 bathrooms
31 Jul – 5 Aug
Guest favourite
Villa in Indigo bay, Sint Maarten, Sint Maarten
Ocean Dream Villa
4.95 out of 5 average rating, 64 reviews, 2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
4 Bedroom Beachfront Condo with Private Pool D2.1
5.0 out of 5 average rating, 20 reviews, 4 bedrooms, 5 beds, 4 bathrooms
18–23 Aug
Top guest favourite
Flat in Cupecoy, Sint Maarten
Stunning oceanfront condo
4.97 out of 5 average rating, 35 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Sept
Top guest favourite
Home in Koolbaai, Sint Maarten
Blue Palm Estate Townhouse w/ Ocean View
4.95 out of 5 average rating, 21 reviews, 2 bedrooms, 3 beds, 3 bathrooms
14–19 Jul
Flat in Simpson Bay, Sint Maarten
Luxury Beachfront Condo
2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Jul
Guest favourite
Flat in Cole Bay, Sint Maarten
Luxurious Sunset Lagoon View
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
24–29 Aug
Luxe
Home in Lowlands, Sint Maarten
Brand NEW - Waterfront Villa - Pool
5.0 out of 5 average rating, 24 reviews, 4 bedrooms, 4 beds, 4 bathrooms
6–11 Jul
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Ocean Breeze at Las Arenas
4.97 out of 5 average rating, 33 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
7–12 Jul
Guest favourite
Flat in Maho Beach, Sint Maarten
Turtle Den YOUR Maho Escape!
4.89 out of 5 average rating, 131 reviews, 1 bedroom, 1 bed, 1 bathroom
28 Jul – 2 Aug
Flat in Simpson Bay, Sint Maarten
Apartment in Simpson bay
New place to stay, 1 bedroom, 2 beds, 1 bathroom
10–15 Jul
Guest favourite
Villa in Indigo Bay, Sint Maarten
Villa Ocean - Indulge Yourself in Paradise
4.95 out of 5 average rating, 77 reviews, 3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
Top guest favourite
Flat in St Martin, St Martin
07 yellow cliff
5.0 out of 5 average rating, 23 reviews, 2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
Top guest favourite
Flat in Cole Bay, Sint Maarten
Beautiful, bright apartment with a lagoon view in Simpson Bay
5.0 out of 5 average rating, 14 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Aug
Superhost
Flat in Cole Bay, Sint Maarten
Sunny Marina Residence
4.83 out of 5 average rating, 24 reviews, 3 bedrooms, 4 beds, 3 bathrooms
19–24 Jul