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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
4–9 Aug
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4.95 out of 5 average rating, 108 reviews
Top guest favourite
Home in Simpson Bay
Villa Blue View .. stunning views of endless sea!
5.0 out of 5 average rating, 92 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
Superhost
Home in Koolbaai
Bahia - Villa 1
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
15–20 Jul
Guest favourite
Townhouse in Sint Maarten
Indigo Bay Villa Poolside - Ocean 14
4.96 out of 5 average rating, 107 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Oct
Guest favourite
Apartment in Simpson Bay
Beachfront Paradise with Pool & Stunning Sunsets
4.9 out of 5 average rating, 68 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
Guest favourite
Flat in Cole Bay
Luxurious Sunset Lagoon View
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
4–9 Aug
Top guest favourite
Apartment in Simpson Bay
Ocean Breeze at Las Arenas
4.97 out of 5 average rating, 33 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
15–20 Jul
Guest favourite
Flat in Cole Bay
Beautiful, bright apartment with a lagoon view in Simpson Bay
5.0 out of 5 average rating, 14 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Aug
Superhost
Flat in Simpson Bay
Luxury Beachfront Condo
2 bedrooms, 2 beds, 2.5 bathrooms
13–18 Jul
Top guest favourite
Home in Koolbaai
Pelican key - BEACH FRONT Villa
5.0 out of 5 average rating, 43 reviews, 3 bedrooms, 5 beds, 3.5 bathrooms
8–13 Sept
Top guest favourite
Flat in Simpson Bay
Villa Harmony Haven
5.0 out of 5 average rating, 65 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
20–25 Jul
Top guest favourite
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
4.99 out of 5 average rating, 98 reviews, 2 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Flat in Simpson Bay
Condo Josephine Maho Beacon Hill
4.79 out of 5 average rating, 14 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Jul
Top guest favourite
Flat in Simpson Bay
Le Papillon -Modern, beachfront, 550sq. ft terrace
5.0 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
1–6 Oct
Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5.0 out of 5 average rating, 26 reviews, 5 bedrooms, 5 beds, 5.5 bathrooms
17–22 Jul
Top guest favourite
Villa in Cole Bay
[Sunset Place] 3BR Oceanfront Villa, Private Pool
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 3 beds, 3 bathrooms
27 Jul – 1 Aug
Top guest favourite
Apartment in Simpson Bay
CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
4.98 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 2 bathrooms
21–26 Jul
Guest favourite
Flat in Simpson Bay
OASIS Penthouse with private garden and Generator
4.92 out of 5 average rating, 52 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
13–18 Jul
Top guest favourite
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
4.99 out of 5 average rating, 328 reviews, 3 bedrooms, 4 beds, 3 bathrooms
28 Sept – 3 Oct