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Search results; Over 1,000 homes in Simpson Bay

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Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
1 bedroom, 1 bed, 1.5 private bathrooms
25–30 Oct
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5.0 out of 5 average rating, 254 reviews
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Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 86 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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Superhost
Flat in Maho Beach
Turtle Den YOUR Maho Escape!
1 bedroom, 1 queen bed, 1 bathroom
29 Oct – 3 Nov
4.86 out of 5 average rating, 145 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, 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 bathroom
1–6 Oct
4.91 out of 5 average rating, 259 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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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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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 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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Top guest favourite
Flat in Simpson Bay
TropiCasa - Watch sunsets surf the waves, 1BR
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 16 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
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Guest favourite
Villa in Lowlands
SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay
3 bedrooms, 3 king beds, 3.5 bathrooms
7–12 Oct
4.77 out of 5 average rating, 154 reviews
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Guest favourite
Hotel in Upper Prince's Quarter
Spacious Deluxe 1BR | Panoramic Ocean View
1 bedroom, 2 beds, 1.5 bathrooms
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 bathroom
1–6 Oct
4.96 out of 5 average rating, 78 reviews
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Guest favourite
Flat in Cole Bay
C354 - Top view with balcony
1 bedroom, 1 king bed, 1 bathroom
16–21 Nov
4.95 out of 5 average rating, 21 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