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Search results; Over 1,000 homes in Simpson Bay

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Top guest favourite
Villa in Simpson Bay, Sint Maarten
Waterfront "Bonjour" Beacon Hill St Maarten
4 bedrooms, 4 beds, 4 private bathrooms
27 Oct – 1 Nov
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4.97 out of 5 average rating, 93 reviews
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Hotel room in Simpson Bay, Sint Maarten
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
31 Oct – 5 Nov
4.87 out of 5 average rating, 276 reviews
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Flat in Simpson Bay, Sint Maarten
The Beach House Apartment
1 bedroom, 1 king bed, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 255 reviews
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Top guest favourite
Townhouse in Sint Maarten, Sint Maarten
Indigo Bay Villa Poolside - Ocean 14
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Oct
4.96 out of 5 average rating, 114 reviews
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Guest favourite
Apartment in Simpson Bay, Sint Maarten
Five Star Luxury Beachfront Condo Private Hot Tub
2 bedrooms, 2 king beds, 2.5 bathrooms
3–8 Oct
4.94 out of 5 average rating, 88 reviews
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Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 king beds, 2.5 bathrooms
10–15 Mar
4.96 out of 5 average rating, 109 reviews
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Top guest favourite
Apartment in Simpson Bay, Sint Maarten
The Penthouse at LaSiesta - 3 BD - Luxury Awaits!
3 bedrooms, 3 king beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 14 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 Oct
5.0 out of 5 average rating, 69 reviews
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Guest favourite
Apartment in Simpson Bay, Sint Maarten
Hamaka condo, a beachfront retreat on Simpson Bay
Business host
1–6 Oct
4.95 out of 5 average rating, 106 reviews
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Guest favourite
Flat in Simpson Bay, Sint Maarten
Top of the art penthouse
3 bedrooms, 4 beds, 3.5 bathrooms
1–6 Oct
4.95 out of 5 average rating, 113 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
1–6 Oct
5.0 out of 5 average rating, 86 reviews
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Top guest favourite
Place to stay in Simpson Bay, Sint Maarten
Your floating B&B at SXM
Individual host
5–10 Dec
5.0 out of 5 average rating, 29 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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Guest favourite
Villa in Simpson Bay, Sint Maarten
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds, 5.5 bathrooms
10–15 Oct
5.0 out of 5 average rating, 29 reviews
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Guest favourite
Flat in Simpson Bay, Sint Maarten
Coco Beachside Duplex
2 bedrooms, 2 beds, 2.5 bathrooms
1–6 Oct
4.93 out of 5 average rating, 42 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 Oct
4.96 out of 5 average rating, 78 reviews
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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
19–24 Oct
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Home in Marigot, St Martin
Beach house, 3 bedrooms, terrace & pool
Individual host
15–20 Oct
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Villa in Lowlands, Sint Maarten
SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay
3 bedrooms, 3 king beds, 3.5 bathrooms
5–10 Oct
4.77 out of 5 average rating, 154 reviews