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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
5–10 Sept
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4.95 out of 5 average rating, 109 reviews
Top guest favourite
Apartment in Simpson Bay
Popular Beachfront Property Barefoot /Simpson bay
2 bedrooms, 2 king beds, 2.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 27 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 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
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
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
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
Flat in Simpson Bay
Vista Blue-Newly Renovated
3 bedrooms, 4 beds, 3.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 24 reviews
Guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool C2.1
Individual host
14–19 Sept
4.9 out of 5 average rating, 20 reviews
Top guest favourite
Flat in Simpson Bay
Simpson bay beach, spacious, beautiful views!
3 bedrooms, 3 king beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 156 reviews
Top guest favourite
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds, 3 bathrooms
11–16 Sept
4.99 out of 5 average rating, 335 reviews
Top guest favourite
Villa in Cole Bay
[Sunset Place] 3BR Oceanfront Villa, Private Pool
3 bedrooms, 3 beds, 3 bathrooms
3–8 Oct
5.0 out of 5 average rating, 14 reviews
Home in Koolbaai
Villa Where Dreams Meet the Sea
2 bedrooms, 2 king beds, 2.5 bathrooms
18–23 Sept
New place to stay
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
Five Star Luxury Beachfront Condo Private Hot Tub
2 bedrooms, 2 king beds, 2.5 bathrooms
5–10 Sept
4.94 out of 5 average rating, 87 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
Apartment in Simpson Bay
Beachfront Ultra Luxury Modern Condo / Beach Views
2 bedrooms, 3 beds, 2.5 bathrooms
5–10 Sept
4.96 out of 5 average rating, 23 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
Flat in Simpson Bay
Top of the art penthouse
3 bedrooms, 4 beds, 3.5 bathrooms
1–6 Oct
4.95 out of 5 average rating, 112 reviews