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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
21–26 Aug
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4.95 out of 5 average rating, 109 reviews
Top guest favourite
Loft in Marigot, St Martin
Sea Loft, Breathtaking View – Private Pool
2 bedrooms, 2 beds, 2 bathrooms
14–19 Oct
4.99 out of 5 average rating, 199 reviews
Home in Koolbaai, Sint Maarten
Waterfront paradise facing the ocean SXM
Individual host
1–6 Sept
New place to stay
Top guest favourite
Apartment in Upper Prince's Quarter, Sint Maarten
Serenity Seascape | 2BR Retreat, 270° Oceanviews
2 bedrooms, 2 king beds, 2.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 81 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
Private Pool- 5 min DRIVE to Maho Beach & Airport
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 75 reviews
Guest favourite
Villa in Indigo bay, Sint Maarten, Sint Maarten
Ocean Dream Villa
2 bedrooms, 2 queen beds, 2 bathrooms
25–30 Aug
4.94 out of 5 average rating, 70 reviews
Top guest favourite
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Poolside - Unit 1
3 bedrooms, 3 beds, 3.5 bathrooms
3–8 Oct
4.98 out of 5 average rating, 45 reviews
Top guest favourite
Flat in Grand Cayes, St Martin
Modern Sea View Apartment from Pinel island
1 bedroom, 1 queen bed, 1 bathroom
26–31 Aug
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and swimming pool access
Individual host
14–19 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
SeaBliss 3BR Palm Beach Condo Simpson Bay
3 bedrooms, 3 beds, 3 bathrooms
10–15 Sept
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Room in Simpson Bay, Sint Maarten
Sanctuary near Maho: Tropical beach vacation stay!
Individual host
22–27 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Villa in Cole Bay, Sint Maarten
[Sunset Place] 3BR Oceanfront Villa, Private Pool
3 bedrooms, 3 beds, 3 bathrooms
3–8 Oct
5.0 out of 5 average rating, 13 reviews
Guest favourite
Villa in Simpson Bay, Sint Maarten
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds, 5.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Villa in Philipsburg, Sint Maarten
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds, 3 bathrooms
1–6 Sept
4.99 out of 5 average rating, 333 reviews
Top guest favourite
Home in Koolbaai, Sint Maarten
Pelican key - BEACH FRONT Villa
Individual host
27 Sept – 2 Oct
5.0 out of 5 average rating, 47 reviews
Guest favourite
Home in Cole Bay, Sint Maarten
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds, 2.5 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 59 reviews
Guest favourite
Apartment in Simpson Bay, Sint Maarten
4 Bedroom Beachfront Condo with Private Pool D2.1
Individual host
6–11 Sept
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Home in Koolbaai, Sint Maarten
Blue Palm Estate Townhouse w/ Ocean View
2 bedrooms, 3 beds, 3 bathrooms
21–26 Aug
4.95 out of 5 average rating, 22 reviews