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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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Townhouse in Simpson Bay
The Drake's "Suite Serenity" @ White Sands Villas
3 bedrooms, 7 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
17–22 Oct
4.91 out of 5 average rating, 58 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
Hotel room in Simpson Bay
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
31 Oct – 5 Nov
4.87 out of 5 average rating, 275 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
Flat in Simpson Bay
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.94 out of 5 average rating, 32 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 bathroom
1–6 Oct
4.91 out of 5 average rating, 259 reviews
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Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 69 reviews
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Guest favourite
Flat in Simpson Bay
Unit 7 - Luxury apartment by the sea
1 bedroom, 1 king bed, 1 bathroom
5–10 Oct
4.93 out of 5 average rating, 80 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, 1 bathroom
7–12 Oct
4.92 out of 5 average rating, 12 reviews
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Guest favourite
Flat in Maho Beach
Escapes at the Emerald – Airport & Beach Nearby
Individual host
20–25 Feb
4.93 out of 5 average rating, 28 reviews
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Superhost
Flat in Simpson Bay
Beachcomb Escape
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Apartment in Simpson Bay
SeaShores Beach Front 1 Brm Apt With Generator SXM
1 bedroom, 2 beds, 1 bathroom
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, 2.5 bathrooms
1–6 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, 1.5 bathrooms
1–6 Oct
4.92 out of 5 average rating, 25 reviews
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Guest favourite
Flat in Simpson Bay
2BR Escape - Walk to Maho and Simpson Bay Beach
2 bedrooms, 2 beds, 1 bathroom
6–11 Oct
4.9 out of 5 average rating, 31 reviews
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Guest favourite
Flat in Pelican
Luxurious Hidden Pearl - Private Pool
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 27 reviews
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Top guest favourite
Villa in Simpson Bay
Surfsong Villa- Luxury Water Front Villa for 12
Business host
25–30 Oct
4.98 out of 5 average rating, 95 reviews