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Search results; Over 1,000 homes in Simpson Bay

Guest favourite
Flat in Simpson Bay
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds, 1 private bathroom
12–17 Oct
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4.94 out of 5 average rating, 32 reviews
Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 84 reviews
Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
13–18 Sept
4.91 out of 5 average rating, 58 reviews
Guest favourite
Hotel room in Simpson Bay
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
13–18 Sept
4.87 out of 5 average rating, 275 reviews
Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 69 reviews
Superhost
Flat in Maho Beach
Turtle Den YOUR Maho Escape!
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.87 out of 5 average rating, 142 reviews
Top guest favourite
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.99 out of 5 average rating, 105 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
Room in Simpson Bay
Sanctuary near Maho: Tropical beach vacation stay!
Individual host
1–6 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
Individual host
13–18 Sept
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Home in Koolbaai
Pelican key - BEACH FRONT Villa
Individual host
27 Sept – 2 Oct
5.0 out of 5 average rating, 48 reviews
Townhouse in Simpson Bay
The Drake’s "Suite Serenity" @ White Sands Villas
3 bedrooms, 6 beds, 3 bathrooms
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Cole Bay
C354 - Top view with balcony
1 bedroom, 1 king bed, 1 bathroom
15–20 Oct
4.95 out of 5 average rating, 21 reviews
Guest favourite
Apartment in Simpson Bay
SeaViews 2Brm Ocean Front Condo SXM
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
4.91 out of 5 average rating, 35 reviews
Guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 60 reviews
Guest favourite
Hotel in Upper Prince's Quarter
1BR Luxury Apartment | Ocean View
1 bedroom, 1 king bed, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Villa in Simpson Bay
Surfsong Villa- Luxury Water Front Villa for 12
6 bedrooms, 6 king beds, 6 bathrooms
20–25 Sept
4.98 out of 5 average rating, 95 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
Guest favourite
Flat in Lowlands
Luxury Maho Studio|Walk to Beach|5 mins to Airport
1 bedroom, 1 queen bed, 1 bathroom
23–28 Sept
4.91 out of 5 average rating, 11 reviews