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Search results; Over 1,000 homes in Simpson Bay

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Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 beds, 3 private bathrooms
1–6 Oct
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4.92 out of 5 average rating, 26 reviews
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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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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
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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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
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, 113 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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Top guest favourite
Villa in Simpson Bay
Surfsong Villa- Luxury Water Front Villa for 12
6 bedrooms, 6 king beds
25–30 Oct
4.98 out of 5 average rating, 95 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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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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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
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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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Townhouse in Simpson Bay
The Drake's "Suite Serenity" @ White Sands Villas
3 bedrooms, 7 beds
4–9 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Flat in Simpson Bay
SeaHarmony 3BR Palm Beach Condo in Simpson Bay
3 bedrooms, 3 king beds
1–6 Oct
4.95 out of 5 average rating, 21 reviews
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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, 105 reviews
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Serviced apartment in Simpson Bay
Unit 3 - Luxury apartment by the sea
1 bedroom, 2 beds
5–10 Oct
4.85 out of 5 average rating, 55 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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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, 275 reviews
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Top guest favourite
Home in Koolbaai
Pelican key - BEACH FRONT Villa
3 bedrooms, 5 beds
1–6 Oct
5.0 out of 5 average rating, 48 reviews