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Search results; Over 1,000 homes in Simpson Bay

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Top guest favourite
Flat in Simpson Bay
Lilly's Beach
1 bedroom, 1 bed, 1 bathroom
4–9 Oct, Individual host
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4.95 out of 5 average rating, 247 reviews
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Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds
17–22 Oct
4.91 out of 5 average rating, 58 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
Apartment in Simpson Bay
Hamaka condo, a beachfront retreat on Simpson Bay
Business host
1–6 Oct
4.95 out of 5 average rating, 106 reviews
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Guest favourite
Flat 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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Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds
1–6 Oct
5.0 out of 5 average rating, 84 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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Top guest favourite
Flat in Simpson Bay
Second Home Beach Apartment
Individual host
17–22 Oct
4.99 out of 5 average rating, 107 reviews
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Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
Individual host
1–6 Oct
4.97 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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Guest favourite
Townhouse in Simpson Bay
Utopia A3 | Beachside Stay @ The Drake Residences
2 bedrooms, 3 beds
12–17 Oct
5.0 out of 5 average rating, 8 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
Hotel in Upper Prince's Quarter
Spacious Deluxe 1BR | Panoramic Ocean View
1 bedroom, 2 beds
1–6 Oct
4.94 out of 5 average rating, 31 reviews
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Guest favourite
Flat in Simpson Bay
Private Pool- 5 min DRIVE to Maho Beach & Airport
1 bedroom, 1 queen bed
1–6 Oct
4.96 out of 5 average rating, 78 reviews
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Guest favourite
Apartment in Simpson Bay
SeaShores Beach Front 1 Brm Apt With Generator SXM
1 bedroom, 2 beds
20–25 Oct
4.95 out of 5 average rating, 58 reviews
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Top guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 61 reviews
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Guest favourite
Flat in Lowlands
Luxury Maho Studio|Walk to Beach|5 mins to Airport
1 bedroom, 1 queen bed
7–12 Oct
4.92 out of 5 average rating, 12 reviews
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Top guest favourite
Flat in Simpson Bay
TropiCasa - Watch sunsets surf the waves, 1BR
1 bedroom, 1 bed
1–6 Oct
5.0 out of 5 average rating, 16 reviews
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Superhost
Flat in Simpson Bay
Beachcomb Escape
1 bedroom, 2 beds
1–6 Oct
5.0 out of 5 average rating, 10 reviews