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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Guest house in Simpson Bay
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 bed, 1 private bathroom
2–7 Sept
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4.95 out of 5 average rating, 109 reviews
Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 82 reviews
Top guest favourite
Room in Simpson Bay
Sanctuary near Maho: Tropical beach vacation stay!
Individual host
4–9 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
3–8 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, 271 reviews
Superhost
Flat in Simpson Bay
2BR Escape - Walk to Maho and Simpson Bay Beach
2 bedrooms, 2 beds, 1 bathroom
18–23 Sept
4.9 out of 5 average rating, 30 reviews
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
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
Townhouse in Simpson Bay
The Drake’s "Suite Serenity" @ White Sands Villas
3 bedrooms, 6 beds, 3 bathrooms
3–8 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds, 5.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 29 reviews
Guest favourite
Flat in Maho Beach
Escapes at the Emerald – Airport & Beach Nearby
Individual host
16–21 Nov
4.92 out of 5 average rating, 26 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
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
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
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
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
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
Apartment in Maho
Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
2–7 Sept
4.91 out of 5 average rating, 257 reviews
Top guest favourite
Flat in Simpson Bay
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds, 1 bathroom
2–7 Sept
4.94 out of 5 average rating, 32 reviews