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Search results; Over 1,000 homes in Simpson Bay

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Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
Studio, 2 beds, 1.5 private bathrooms
2–7 Sept
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5.0 out of 5 average rating, 81 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
A waterfront paradise facing the ocean on Saint Martin
4 bedrooms, 6 beds, 3 bathrooms
1–6 Sept
New place to stay
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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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Superhost
Home in Lowlands
Villa Calma – Lagoon view, swimming pool & tranquility
3 bedrooms, 4 beds, 3.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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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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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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Guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool C2.1
4 bedrooms, 5 beds, 4 bathrooms
26 Sept – 1 Oct
4.89 out of 5 average rating, 19 reviews
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Guest favourite
Flat in Simpson Bay
Royal Palm Hilton Penthouse
3 bedrooms, 3 king beds, 3 bathrooms
3–10 Sept
5.0 out of 5 average rating, 8 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
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
Apartment in Simpson Bay
Five Star Luxury Beachfront Condo Private Hot Tub
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Sept
4.94 out of 5 average rating, 87 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
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 Indigo bay, Sint Maarten
Ocean Dream Villa
2 bedrooms, 2 queen beds, 2 bathrooms
12–17 Sept
4.94 out of 5 average rating, 71 reviews
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Top guest favourite
Villa in Cole Bay
[Sunset Place] 3BR Oceanfront Villa, Private Pool
3 bedrooms, 3 beds, 3 bathrooms
3–8 Oct
5.0 out of 5 average rating, 14 reviews