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Search results; Over 1,000 homes in Simpson Bay

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Guest favourite
Apartment in Simpson Bay
CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
2 bedrooms, 2 beds, 2 private bathrooms
11–16 Sept
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4.96 out of 5 average rating, 54 reviews
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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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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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Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 44 reviews
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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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Flat in Simpson Bay
Royal Palm Hilton SXM
2 bedrooms, 3 beds, 2 bathrooms
3–10 Sept
4.92 out of 5 average rating, 66 reviews
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Villa in Simpson Bay
Surfsong Villa- Luxury Water Front Villa for 12
6 bedrooms, 6 king beds, 6 bathrooms
20–25 Sept
4.98 out of 5 average rating, 94 reviews
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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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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, 13 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
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Townhouse in Simpson Bay
The Drake's "Suite Serenity" @ White Sands Villas
3 bedrooms, 6 beds, 3 bathrooms
1–6 Sept
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Apartment in Upper Prince's Quarter
Serenity Seascape | 2BR Retreat, 270° Oceanviews
2 bedrooms, 2 king beds, 2.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 7 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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Villa in Koolbaai
Villa Livity 6 Bed Luxury Sea view boutique villa
6 bedrooms, 6 beds, 6.5 bathrooms
5–10 Sept
4.91 out of 5 average rating, 46 reviews
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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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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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Home in Koolbaai
Villa Where Dreams Meet the Sea
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Sept
New place to stay
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Room in Upper Prince's Quarter
1BR Luxury Apartment | Ocean View
1 king bed, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 18 reviews
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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