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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
Apartment in Philipsburg
Flamingo Beach by Hilton Grand Vacations- studio
1 bathroom
12–17 Sept
Top guest favourite
Apartment in Simpson Bay
Ocean Breeze at Las Arenas
4.97 out of 5 average rating, 32 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
6–11 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
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
Top guest favourite
Home in Koolbaai
Pelican key - BEACH FRONT Villa
5.0 out of 5 average rating, 43 reviews, 3 bedrooms, 5 beds, 3.5 bathrooms
11–16 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
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
Top 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
31 Jul – 5 Aug
Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
4.92 out of 5 average rating, 24 reviews, 3 bedrooms, 3 beds, 3 bathrooms
9–14 Aug
Guest favourite
Flat in Simpson Bay
Apartment on the beach
4.88 out of 5 average rating, 243 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Jul
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
Flat in Simpson Bay
Luxury Beachfront Condo
2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Jul
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
6–11 Jul
Top guest favourite
Apartment in Simpson Bay
CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
4.98 out of 5 average rating, 50 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
5.0 out of 5 average rating, 244 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
1–6 Aug
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
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