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Search results; Over 1,000 homes in Simpson Bay

Guest favourite
Apartment in Simpson Bay
Beachfront Paradise with Pool & Stunning Sunsets
2 bedrooms, 3 beds, 2 private bathrooms
9–14 Sept
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4.9 out of 5 average rating, 72 reviews
Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds
5–10 Sept
5.0 out of 5 average rating, 69 reviews
Top guest favourite
Home in Koolbaai
Pelican key - BEACH FRONT Villa
3 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Villa in Simpson Bay
Surfsong Villa- Luxury Water Front Villa for 12
6 bedrooms, 6 king beds
25–30 Oct
4.98 out of 5 average rating, 95 reviews
Top guest favourite
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds
6–11 Sept
4.99 out of 5 average rating, 104 reviews
Top guest favourite
Apartment in Simpson Bay
Popular Beachfront Property Barefoot /Simpson bay
2 bedrooms, 2 king beds
4–9 Sept
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds
11–16 Sept
4.99 out of 5 average rating, 335 reviews
Top guest favourite
Flat in Simpson Bay
Vista Blue-Newly Renovated
3 bedrooms, 4 beds
4–9 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
4 bedrooms, 5 beds
14–19 Sept
4.9 out of 5 average rating, 20 reviews
Top guest favourite
Home in Cole Bay
Puerta Al Mar - Ocean-Side Villa Tranquility
5 bedrooms, 5 beds
12–17 Oct
5.0 out of 5 average rating, 52 reviews
Home in Koolbaai
Villa Where Dreams Meet the Sea
2 bedrooms, 2 king beds
13–18 Sept
New place to stay
Top guest favourite
Villa in Cole Bay
[Sunset Place] 3BR Oceanfront Villa, Private Pool
3 bedrooms, 3 beds
3–8 Oct
5.0 out of 5 average rating, 14 reviews
Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds
12–17 Sept
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Apartment in Simpson Bay
The Penthouse at LaSiesta - 3 BD - Luxury Awaits!
3 bedrooms, 3 king beds
12–17 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Apartment in Simpson Bay
SkyPort Condo
2 bedrooms, 2 beds
20–25 Oct
4.98 out of 5 average rating, 87 reviews
Guest favourite
Villa in Koolbaai
Villa Livity 6 Bed Luxury Sea view boutique villa
6 bedrooms, 6 beds
5–10 Sept
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Flat in Simpson Bay
Stunning Boho-Chic Beach Condo with Rooftop
2 bedrooms, 2 beds
11–16 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Simpson Bay
Simpson bay beach, spacious, beautiful views!
3 bedrooms, 3 king beds
7–12 Sept
5.0 out of 5 average rating, 156 reviews
Guest favourite
Townhouse in Simpson Bay
Utopia A3 | Beachside Stay @ The Drake Residences
2 bedrooms, 3 beds
18–23 Sept
5.0 out of 5 average rating, 7 reviews