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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Flat in Simpson Bay
Lilly's Beach
1 bedroom, 1 bed, 1 bathroom
14–19 Sept, Individual host
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4.95 out of 5 average rating, 246 reviews
Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 82 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
Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
7–12 Sept
4.91 out of 5 average rating, 57 reviews
Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 69 reviews
Top guest favourite
Flat in Simpson Bay
Apartment on the beach 2
Individual host
11–16 Sept
4.86 out of 5 average rating, 207 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
Flat in Lowlands
Stunning Gem in Prime Location
1 bedroom, 2 beds, 2 bathrooms
7–12 Sept
4.92 out of 5 average rating, 51 reviews
Guest favourite
Flat in Simpson Bay
Unit 7 - Luxury apartment by the sea
1 bedroom, 1 king bed, 1 bathroom
16–21 Sept
4.93 out of 5 average rating, 80 reviews
Top guest favourite
Apartment in Maho
Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
5–10 Sept
4.91 out of 5 average rating, 257 reviews
Townhouse in Simpson Bay
The Drake’s "Suite Serenity" @ White Sands Villas
3 bedrooms, 6 beds, 3 bathrooms
6–11 Sept
5.0 out of 5 average rating, 3 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
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
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
Individual host
27 Sept – 2 Oct
4.96 out of 5 average rating, 27 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
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Poolside - Unit 1
3 bedrooms, 3 beds, 3.5 bathrooms
3–8 Oct
4.98 out of 5 average rating, 47 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
Top guest favourite
Flat in Simpson Bay
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds, 1 bathroom
5–10 Sept
4.94 out of 5 average rating, 32 reviews