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Search results; Over 1,000 homes in Simpson Bay

Superhost
Room in Simpson Bay
White Sands Tropical Garden
1 bedroom, 1 bed, 1 private bathroom
14–19 Sept
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4.91 out of 5 average rating, 116 reviews
Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
4–9 Sept
5.0 out of 5 average rating, 82 reviews
Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 69 reviews
Guest favourite
Hotel room in Simpson Bay
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
24–29 Sept
4.87 out of 5 average rating, 272 reviews
Townhouse in Simpson Bay
The Drake’s "Suite Serenity" @ White Sands Villas
3 bedrooms, 6 beds, 3 bathrooms
5–10 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Simpson Bay
SeaBliss 3BR Palm Beach Condo Simpson Bay
3 bedrooms, 3 beds, 3 bathrooms
10–15 Sept
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Flat in Simpson Bay
Apartment on the beach 2
Individual host
11–16 Sept
4.85 out of 5 average rating, 206 reviews
Guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool C2.1
Individual host
26 Sept – 1 Oct
4.9 out of 5 average rating, 20 reviews
Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
1 bedroom, 1 king bed, 1.5 bathrooms
24–29 Sept
5.0 out of 5 average rating, 252 reviews
Top guest favourite
Apartment in Maho
Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
4–9 Sept
4.91 out of 5 average rating, 257 reviews
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds, 3.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 44 reviews
Top guest favourite
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.99 out of 5 average rating, 104 reviews
Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds, 3 bathrooms
1–6 Oct
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Simpson Bay
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds, 1 bathroom
4–9 Sept
4.94 out of 5 average rating, 32 reviews
Top guest favourite
Flat in Cupecoy
Stunning oceanfront condo
2 bedrooms, 2 king beds, 2.5 bathrooms
15–20 Sept
4.98 out of 5 average rating, 40 reviews
Guest favourite
Townhouse in Simpson Bay
Utopia A3 | Beachside Stay @ The Drake Residences
2 bedrooms, 3 beds, 2.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 60 reviews
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
Superhost
Flat in Maho Beach
Turtle Den YOUR Maho Escape!
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
4.87 out of 5 average rating, 141 reviews