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Search results; Over 1,000 homes in Simpson Bay

Guest favourite
Apartment in Simpson Bay
CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
2 bedrooms, 2 beds, 2 private bathrooms
11–16 Sept
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4.96 out of 5 average rating, 55 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
Top guest favourite
Apartment in Simpson Bay
Popular Beachfront Property Barefoot /Simpson bay
2 bedrooms, 2 king beds, 2.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 27 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
Home in Cole Bay
Puerta Al Mar - Ocean-Side Villa Tranquility
5 bedrooms, 5 beds, 5.5 bathrooms
12–17 Oct
5.0 out of 5 average rating, 52 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
Home in Koolbaai
A waterfront paradise facing the ocean on Saint Martin
4 bedrooms, 6 beds, 3 bathrooms
2–7 Sept
New place to stay
Top guest favourite
Apartment in Upper Prince's Quarter
Serenity Seascape | 2BR Retreat, 270° Oceanviews
2 bedrooms, 2 king beds, 2.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Simpson Bay
Vista Blue-Newly Renovated
3 bedrooms, 4 beds, 3.5 bathrooms
3–8 Sept
5.0 out of 5 average rating, 24 reviews
Superhost
Flat in Cupecoy
Ocean Paradise Condo - The Cliff
4 bedrooms, 4 beds, 4.5 bathrooms
6–11 Sept
New place to stay
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
Flat in Cupecoy
Stunning oceanfront condo
2 bedrooms, 2 beds, 2.5 bathrooms
15–20 Sept
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 king beds, 2.5 bathrooms
16–21 Oct
4.96 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
Guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool C2.1
4 bedrooms, 5 beds, 4 bathrooms
26 Sept – 1 Oct
4.9 out of 5 average rating, 20 reviews
Top guest favourite
Apartment in Simpson Bay
The Penthouse at LaSiesta - 3 BD - Luxury Awaits!
3 bedrooms, 3 king beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Cole Bay
Beautiful, bright apartment with a lagoon view in Simpson Bay
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 21 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
Home in Koolbaai
Villa Where Dreams Meet the Sea
2 bedrooms, 2 king beds, 2.5 bathrooms
13–18 Sept
New place to stay