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Search results; Over 1,000 homes in Simpson Bay

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Guest favourite
Apartment in Simpson Bay, Sint Maarten
Hamaka condo, a beachfront retreat on Simpson Bay
1 bedroom, 2 beds, 1 private bathroom
1–6 Sept
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4.95 out of 5 average rating, 106 reviews
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Guest favourite
Flat in Simpson Bay, Sint Maarten
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 68 reviews
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Townhouse in Simpson Bay, Sint Maarten
The Drake's "Suite Serenity" @ White Sands Villas
3 bedrooms, 6 beds, 3 bathrooms
1–6 Sept
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Guest favourite
Apartment in Simpson Bay, Sint Maarten
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds, 4 bathrooms
6–11 Sept
4.96 out of 5 average rating, 26 reviews
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Guest favourite
Hotel room in Simpson Bay, Sint Maarten
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
18–23 Sept
4.87 out of 5 average rating, 270 reviews
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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
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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
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Guest favourite
Flat in Simpson Bay, Sint Maarten
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
7–12 Sept
4.91 out of 5 average rating, 56 reviews
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Room in Simpson Bay, Sint Maarten
Sanctuary near Maho: Tropical beach vacation stay!
1 double bed, 1 bathroom
4–9 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Serviced apartment in Simpson Bay, Sint Maarten
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.94 out of 5 average rating, 32 reviews
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Guest favourite
Room in Upper Prince's Quarter, Sint Maarten
1BR Luxury Apartment | Ocean View
1 king bed, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and pool access
3 bedrooms, 3 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Flat in Cole Bay, Sint Maarten
C354 - Top view with balcony
1 bedroom, 1 king bed, 1 bathroom
8–13 Oct
4.95 out of 5 average rating, 20 reviews
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Guest favourite
Flat in Grand-Case, St Martin
NEW: Unmatched Oceanfront Living in Grand Case
2 bedrooms, 2 beds, 2 bathrooms
21–26 Sept
4.88 out of 5 average rating, 26 reviews
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Guest favourite
Apartment in Little Bay, Sint Maarten
Maazoon -Luxury modern 3BR Apt for 6 – Central SXM
3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
4.94 out of 5 average rating, 18 reviews
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Guest favourite
Flat in Simpson Bay, Sint Maarten
Private Pool- 5 min DRIVE to Maho Beach & Airport
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
4.96 out of 5 average rating, 76 reviews
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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, 141 reviews
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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
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Top guest favourite
Villa in Philipsburg, Sint Maarten
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds, 3 bathrooms
14–19 Apr
4.99 out of 5 average rating, 334 reviews