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Search results; Over 1,000 homes in Simpson Bay

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Top guest favourite
Guest house in Simpson Bay
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 bed, 1 private bathroom
1–6 Sept
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4.95 out of 5 average rating, 109 reviews
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Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 69 reviews
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Top guest favourite
Apartment in Simpson Bay
Popular Beachfront Property Barefoot /Simpson bay
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 27 reviews
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Home in Koolbaai
Waterfront paradise facing the ocean SXM
Individual host
1–6 Sept
New place to stay
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Top guest favourite
Flat in Simpson Bay
Vista Blue-Newly Renovated
3 bedrooms, 4 beds, 3.5 bathrooms
3–8 Sept
5.0 out of 5 average rating, 24 reviews
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Guest favourite
Flat in Simpson Bay
Dolphin - cosy 2BR apt, 50m Simpson Bay beach
2 bedrooms, 3 beds, 1 bathroom
1–8 Sept
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds, 5.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 29 reviews
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Top guest favourite
Home in Cole Bay
Puerta Al Mar - Ocean-Side Villa Tranquility
5 bedrooms, 5 beds, 5.5 bathrooms
12–17 Oct
5.0 out of 5 average rating, 52 reviews
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Guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
Individual host
13–18 Sept
4.96 out of 5 average rating, 26 reviews
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Townhouse in Simpson Bay
The Drake's "Suite Serenity" @ White Sands Villas
3 bedrooms, 6 beds, 3 bathrooms
2–7 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Simpson Bay
Le Papillon -Modern, beachfront, 550sq. ft terrace
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 53 reviews
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Top guest favourite
Apartment in Simpson Bay
The Penthouse at LaSiesta - 3 BD - Luxury Awaits!
3 bedrooms, 3 king beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 14 reviews
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Guest favourite
Villa in Koolbaai
Villa Livity 6 Bed Luxury Sea view boutique villa
Business host
5–10 Sept
4.91 out of 5 average rating, 46 reviews
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Top guest favourite
Apartment in Simpson Bay
SkyPort Condo
2 bedrooms, 2 beds, 2.5 bathrooms
20–25 Oct
4.98 out of 5 average rating, 86 reviews
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Home in Koolbaai
Villa Where Dreams Meet the Sea
2 bedrooms, 2 king beds, 2.5 bathrooms
13–18 Sept
New place to stay
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Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds, 3 bathrooms
1–6 Oct
4.92 out of 5 average rating, 26 reviews
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Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 81 reviews
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Top guest favourite
Apartment in Cole Bay
Royal Palm-1st floor-walk right out to the beach
2 bedrooms, 3 beds, 2 bathrooms
2–8 Sept
5.0 out of 5 average rating, 36 reviews
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Home in Lowlands
#1 Unique luxury villa, pool & stunning sea views
4 bedrooms, 5 beds, 4.5 bathrooms
14–19 Sept