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Search results; Over 1,000 homes in Simpson Bay

Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
Studio, 2 beds, 1.5 private bathrooms
21–26 Sept
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5.0 out of 5 average rating, 83 reviews
Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds
11–16 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, 48 reviews
Guest favourite
Villa in Cole Bay
Pelican Key*Amazing VIEWS! Private Pool *
5 bedrooms, 5 beds
10–15 Sept
4.91 out of 5 average rating, 46 reviews
Townhouse in Simpson Bay
The Drake’s "Suite Serenity" @ White Sands Villas
3 bedrooms, 6 beds
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds
10–15 Sept
4.99 out of 5 average rating, 105 reviews
Top guest favourite
Apartment in Simpson Bay
Popular Beachfront Property Barefoot /Simpson bay
2 bedrooms, 2 king beds
10–15 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
6 bedrooms, 6 king beds
20–25 Sept
4.98 out of 5 average rating, 95 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, 21 reviews
Guest favourite
Flat in Simpson Bay
Royal Palm Hilton SXM
2 bedrooms, 3 beds
12–19 Sept
4.92 out of 5 average rating, 66 reviews
Home in Koolbaai
Villa Where Dreams Meet the Sea
2 bedrooms, 2 king beds
18–23 Sept
New place to stay
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
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds
21–26 Nov
4.99 out of 5 average rating, 335 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
Guest favourite
Flat in Simpson Bay
Top of the art penthouse
3 bedrooms, 4 beds
1–6 Oct
4.95 out of 5 average rating, 112 reviews
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds
10–15 Sept
5.0 out of 5 average rating, 44 reviews
Guest favourite
Villa in Koolbaai
Villa Livity 6 Bed Luxury Sea view boutique villa
6 bedrooms, 6 beds
11–16 Sept
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Home in Cole Bay
Puerta Al Mar - Ocean-Side Villa Tranquility
5 bedrooms, 5 beds
12–17 Oct
4.98 out of 5 average rating, 53 reviews
Guest favourite
Apartment in Simpson Bay
Beachfront Paradise with Pool & Stunning Sunsets
2 bedrooms, 3 beds
22–27 Oct
4.9 out of 5 average rating, 72 reviews