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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Guest house in Simpson Bay, Sint Maarten
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 bed, 1 private bathroom
1–6 Sept
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4.95 out of 5 average rating, 109 reviews
Guest favourite
Hotel room in Simpson Bay, Sint Maarten
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
7–12 Sept
4.87 out of 5 average rating, 269 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 81 reviews
Guest favourite
Room in Upper Prince's Quarter, Sint Maarten
1BR Luxury Apartment | Ocean View
1 king bed, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Apartment in Simpson Bay, Sint Maarten
Beachfront Paradise with Pool & Stunning Sunsets
2 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
4.9 out of 5 average rating, 70 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
The Beach Condo
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Sept
4.99 out of 5 average rating, 83 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Popular Beachfront Property Barefoot /Simpson bay
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 27 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
Apartment on the beach
Individual host
5–10 Sept
4.89 out of 5 average rating, 245 reviews
Home in Koolbaai, Sint Maarten
Villa Where Dreams Meet the Sea
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Sept
New place to stay
Top guest favourite
Flat in Simpson Bay, Sint Maarten
The Pineapple Suite
2 bedrooms, 2 queen beds, 1 bathroom
14–19 Sept
4.96 out of 5 average rating, 47 reviews
Guest favourite
Flat in Grand-Case, St Martin
NEW: Unmatched Oceanfront Living in Grand Case
2 bedrooms, 2 beds, 2 bathrooms
30 Nov – 5 Dec
4.88 out of 5 average rating, 26 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
Lilly's Beach
Individual host
1–6 Sept
4.95 out of 5 average rating, 244 reviews
Top guest favourite
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Middle Floor - Unit 2
3 bedrooms, 3 beds, 3.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Flat in Lowlands, Sint Maarten
Garden Side 2 Large Studio
1 queen bed, 1 bathroom
8–13 Sept
4.97 out of 5 average rating, 151 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Stunning Boho-Chic Beach Condo with Rooftop
2 bedrooms, 2 beds, 2 bathrooms
1–8 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Le Papillon -Modern, beachfront, 550sq. ft terrace
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 53 reviews
Top guest favourite
Place to stay in Simpson Bay, Sint Maarten
Your floating B&B at SXM
Individual host
2–7 Dec
5.0 out of 5 average rating, 29 reviews
Guest favourite
Flat in Saint Martin, St Martin
On the beach! Villa Marina pool splendid view
Individual host
1–6 Sept
4.95 out of 5 average rating, 79 reviews
Guest favourite
Villa in Simpson Bay, Sint Maarten
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, 28 reviews