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Search results; Over 1,000 homes in Simpson Bay

Guest favourite
Flat in Simpson Bay, Sint Maarten
A Wave From It All - Gorgeous Beachfront Condo
2 bedrooms, 2 beds, 2.5 bathrooms
1–6 Oct
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5.0 out of 5 average rating, 6 reviews
Townhouse in Simpson Bay, Sint Maarten
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
Flat in Simpson Bay, Sint Maarten
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 69 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
SeaBliss 3BR Palm Beach Condo Simpson Bay
3 bedrooms, 3 beds, 3 bathrooms
25–30 Sept
4.98 out of 5 average rating, 42 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
28 Sept – 3 Oct
4.96 out of 5 average rating, 77 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
SkyPort Condo
2 bedrooms, 2 beds, 2.5 bathrooms
20–25 Oct
4.98 out of 5 average rating, 87 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, 29 reviews
Guest favourite
Hotel room in Simpson Bay, Sint Maarten
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
10–15 Sept
4.87 out of 5 average rating, 275 reviews
Guest favourite
Home in Cole Bay, Sint Maarten
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 60 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
The Beach House Apartment
1 bedroom, 1 king bed, 1.5 bathrooms
16–21 Apr
5.0 out of 5 average rating, 253 reviews
Guest favourite
Serviced apartment in Simpson Bay, Sint Maarten
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.94 out of 5 average rating, 32 reviews
Top guest favourite
Villa in Little Bay, Sint Maarten
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.99 out of 5 average rating, 105 reviews
Home in Koolbaai, Sint Maarten
A waterfront paradise facing the ocean on Saint Martin
4 bedrooms, 6 beds, 3 bathrooms
1–6 Oct
New place to stay
Guest favourite
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and pool access
3 bedrooms, 3 king beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds, 4 bathrooms
13–18 Sept
4.96 out of 5 average rating, 28 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 83 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds, 3 bathrooms
1–6 Oct
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Guest house in Simpson Bay, Sint Maarten
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 queen bed, 1 bathroom
9–14 Sept
4.95 out of 5 average rating, 109 reviews
Superhost
Flat in Maho Beach, Sint Maarten
Turtle Den YOUR Maho Escape!
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
4.87 out of 5 average rating, 142 reviews