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Search results; Over 1,000 homes in Simpson Bay

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Top guest favourite
Apartment in Simpson Bay
Ocean Breeze at Las Arenas
3 bedrooms, 3 beds, 3.5 private bathrooms
1–6 Oct
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4.97 out of 5 average rating, 33 reviews
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Guest favourite
Apartment in Simpson Bay
Hamaka condo, a beachfront retreat on Simpson Bay
Business host
25–30 Sept
4.95 out of 5 average rating, 106 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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Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
Individual host
20–25 Sept
4.97 out of 5 average rating, 29 reviews
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Top guest favourite
Flat in Simpson Bay
Simpson bay beach, spacious, beautiful views!
3 bedrooms, 3 king beds
18–23 Sept
5.0 out of 5 average rating, 157 reviews
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Top guest favourite
Villa in Simpson Bay
Surfsong Villa- Luxury Water Front Villa for 12
Business host
20–25 Sept
4.98 out of 5 average rating, 95 reviews
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Guest favourite
Flat in Simpson Bay
2BR Escape - Walk to Maho and Simpson Bay Beach
2 bedrooms, 2 beds
19–24 Sept
4.9 out of 5 average rating, 31 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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Superhost
Apartment in Simpson Bay
Maho Beach Oceanfront Getaway
1 bedroom, 2 beds
28 Sept – 3 Oct
4.67 out of 5 average rating, 231 reviews
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Top guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 61 reviews
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Top guest favourite
Hotel in Upper Prince's Quarter
1BR Luxury Apartment | Ocean View
1 bedroom, 1 king bed
19–24 Sept
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Apartment in Simpson Bay
The Beach Condo
2 bedrooms, 2 king beds
17–22 Sept
4.99 out of 5 average rating, 83 reviews
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Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds
23–28 Dec
5.0 out of 5 average rating, 84 reviews
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Townhouse in Simpson Bay
"Suite Serenity" @ White Sands Villas
3 bedrooms, 6 beds
18–23 Sept
5.0 out of 5 average rating, 4 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
28 Sept – 3 Oct
4.96 out of 5 average rating, 78 reviews
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Top guest favourite
Flat in Simpson Bay
Second Home Beach Apartment
Individual host
20–25 Sept
4.99 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
Flat in Simpson Bay
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds
18–23 Oct
4.94 out of 5 average rating, 32 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