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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 beds, 2.5 private bathrooms
16–21 Oct
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4.97 out of 5 average rating, 106 reviews
Top guest favourite
Home in Simpson Bay
Villa Blue View .. stunning views of endless sea!
5.0 out of 5 average rating, 92 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
Top guest favourite
Apartment in Simpson Bay
Ocean Breeze at Las Arenas
4.97 out of 5 average rating, 33 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
8–13 Jul
Guest favourite
Villa in Simpson Bay
Waterfront "Bonjour" Beacon Hill St Maarten
4.97 out of 5 average rating, 86 reviews, 4 bedrooms, 4 beds, 4 bathrooms
7–12 Jul
Guest favourite
Apartment in Simpson Bay
Beachfront Paradise with Pool & Stunning Sunsets
4.9 out of 5 average rating, 68 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Home in Koolbaai
Bahia - Villa 1
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
21–28 Jul
Guest favourite
Townhouse in Sint Maarten
Indigo Bay Villa Poolside - Ocean 14
4.96 out of 5 average rating, 106 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Oct
Guest favourite
Villa in Simpson Bay
Villa Myles: Beachfront
4.79 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
7–12 Jul
Top guest favourite
Flat in Simpson Bay
Apartment on the beach 2
4.85 out of 5 average rating, 200 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Jul
Top guest favourite
Flat in Cole Bay
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
Top guest favourite
Apartment in Simpson Bay
Beachside Escape
4.96 out of 5 average rating, 27 reviews, 2 bedrooms, 3 beds, 2 bathrooms
9–14 Jul
Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
5.0 out of 5 average rating, 76 reviews, 2 beds, 1.5 bathrooms
1–6 Sept
Top guest favourite
Flat in Simpson Bay
Villa Harmony Haven
5.0 out of 5 average rating, 64 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
13–18 Jul
Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5.0 out of 5 average rating, 25 reviews, 5 bedrooms, 5 beds, 5.5 bathrooms
17–22 Jul
Top guest favourite
Villa in Cole Bay
[Sunset Place] 3BR Oceanfront Villa, Private Pool
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 3 beds, 3 bathrooms
27 Jul – 1 Aug
Flat in Simpson Bay
Luxury Beachfront Condo
2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Jul
Top guest favourite
Flat in Simpson Bay
Le Papillon -Modern, beachfront, 550sq. ft terrace
5.0 out of 5 average rating, 49 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
21–26 Aug
Guest favourite
Flat in Simpson Bay
Top of the art penthouse
4.95 out of 5 average rating, 110 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
1–6 Aug
Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
5.0 out of 5 average rating, 20 reviews, 4 bedrooms, 5 beds, 4 bathrooms
12–17 Jul