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Search results; Over 1,000 homes in Simpson Bay

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Guest favourite
Flat in Simpson Bay
Top of the art penthouse
3 bedrooms, 4 beds, 3.5 private bathrooms
1–6 Oct
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4.95 out of 5 average rating, 113 reviews
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Top guest favourite
Villa in Simpson Bay
Waterfront "Bonjour" Beacon Hill St Maarten
4 bedrooms, 4 king beds
27 Oct – 1 Nov
4.97 out of 5 average rating, 93 reviews
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Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds
1–6 Oct
5.0 out of 5 average rating, 69 reviews
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Guest favourite
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds
25–30 Oct
4.99 out of 5 average rating, 339 reviews
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Guest favourite
Apartment in Simpson Bay
Hamaka condo, a beachfront retreat on Simpson Bay
1 bedroom, 2 beds
1–6 Oct
4.95 out of 5 average rating, 106 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
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
3–8 Oct
4.94 out of 5 average rating, 88 reviews
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Top guest favourite
Apartment in Upper Prince's Quarter
Serenity Seascape | 2BR Retreat, 270° Oceanviews
2 bedrooms, 2 king beds
19–24 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Townhouse in Sint Maarten
Indigo Bay Villa Poolside - Ocean 14
2 bedrooms, 2 king beds
1–6 Oct
4.96 out of 5 average rating, 114 reviews
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Top guest favourite
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds
11–16 Oct
4.99 out of 5 average rating, 106 reviews
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Guest favourite
Villa in Lowlands
SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay
3 bedrooms, 3 king beds
5–10 Oct
4.77 out of 5 average rating, 154 reviews
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Guest favourite
Hotel room in Simpson Bay
Azure Hotel Bay Suite
1 bedroom, 1 single bed
31 Oct – 5 Nov
4.87 out of 5 average rating, 276 reviews
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Top guest favourite
Apartment in Maho
Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub
1 bedroom, 1 queen bed
1–6 Oct
4.91 out of 5 average rating, 259 reviews
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Guest favourite
Apartment in Simpson Bay
Beachfront Paradise with Pool & Stunning Sunsets
2 bedrooms, 4 beds
22–27 Oct
4.9 out of 5 average rating, 73 reviews
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Guest favourite
Serviced apartment in Simpson Bay
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds
1–6 Oct
4.94 out of 5 average rating, 32 reviews
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Top guest favourite
Home in Koolbaai
Pelican key - BEACH FRONT Villa
3 bedrooms, 5 beds
13–18 Oct
5.0 out of 5 average rating, 48 reviews
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Guest favourite
Villa in Koolbaai
Sol y Mar - Beachfront Penthouse with private pool
3 bedrooms, 4 beds
1–6 Oct
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds
10–15 Oct
5.0 out of 5 average rating, 29 reviews
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Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Middle Floor - Unit 2
3 bedrooms, 3 beds
10–15 Oct
4.97 out of 5 average rating, 38 reviews