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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Flat in Simpson Bay
Second Home Beach Apartment
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept, Individual host
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4.99 out of 5 average rating, 106 reviews
Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 69 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
Top guest favourite
Apartment in Simpson Bay
Popular Beachfront Property Barefoot /Simpson bay
2 bedrooms, 2 king beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Villa in Simpson Bay
Surfsong Villa- Luxury Water Front Villa for 12
Business host
25–30 Oct
4.98 out of 5 average rating, 95 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
Flat in Simpson Bay
Simpson bay beach, spacious, beautiful views!
3 bedrooms, 3 king beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 156 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
Flat in Simpson Bay
Royal Palm Hilton SXM
2 bedrooms, 3 beds, 2 bathrooms
9–16 Sept
4.92 out of 5 average rating, 66 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, 21 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
Villa in Koolbaai
Villa Livity 6 Bed Luxury Sea view boutique villa
Business host
8–13 Sept
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.99 out of 5 average rating, 105 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
4.98 out of 5 average rating, 53 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
Waterfront paradise facing the ocean SXM
Individual host
1–6 Oct
New place to stay
Guest favourite
Apartment in Simpson Bay
Beachfront Paradise with Pool & Stunning Sunsets
2 bedrooms, 3 beds, 2 bathrooms
28 Oct – 4 Nov
4.9 out of 5 average rating, 72 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, 47 reviews
Guest favourite
Villa in Cole Bay
Pelican Key*Amazing VIEWS! Private Pool *
5 bedrooms, 5 beds, 4 bathrooms
8–13 Sept
4.91 out of 5 average rating, 46 reviews