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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 beds, 3 private bathrooms
1–6 Oct
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4.92 out of 5 average rating, 26 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
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
Waterfront paradise facing the ocean SXM
Individual host
2–7 Sept
New place to stay
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
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
Top guest favourite
Villa in Simpson Bay
Surfsong Villa- Luxury Water Front Villa for 12
Business host
20–25 Sept
4.98 out of 5 average rating, 94 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
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
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
Guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool C2.1
Individual host
26 Sept – 1 Oct
4.9 out of 5 average rating, 20 reviews
Top guest favourite
Villa in Simpson Bay
Waterfront "Bonjour" Beacon Hill St Maarten
4 bedrooms, 4 king beds, 4 bathrooms
22–27 Oct
4.97 out of 5 average rating, 90 reviews
Guest favourite
Apartment in Simpson Bay
Beachfront Paradise with Pool & Stunning Sunsets
2 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
4.9 out of 5 average rating, 72 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
Villa in Koolbaai
Villa Livity 6 Bed Luxury Sea view boutique villa
Business host
5–10 Sept
4.91 out of 5 average rating, 46 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
Top guest favourite
Apartment in Simpson Bay
SkyPort Condo
2 bedrooms, 2 beds, 2.5 bathrooms
20–25 Oct
4.98 out of 5 average rating, 87 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