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Search results; Over 1,000 homes in Simpson Bay

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Top guest favourite
Flat in Simpson Bay, Sint Maarten
Lilly's Beach
1 bedroom, 1 bed, 1 bathroom
4–9 Oct, Individual host
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4.95 out of 5 average rating, 247 reviews
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Guest favourite
Apartment in Simpson Bay, Sint Maarten
Hamaka condo, a beachfront retreat on Simpson Bay
Business host
25–30 Sept
4.95 out of 5 average rating, 106 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
31 Oct – 5 Nov
4.87 out of 5 average rating, 275 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
Townhouse in Sint Maarten, Sint Maarten
Indigo Bay Villa Poolside - Ocean 14
2 bedrooms, 2 king beds, 2.5 bathrooms
29 Sept – 4 Oct
4.96 out of 5 average rating, 113 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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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
20–25 Sept
4.95 out of 5 average rating, 109 reviews
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Top guest favourite
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Middle Floor - Unit 2
3 bedrooms, 3 beds, 3.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 38 reviews
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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, 48 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
28 Sept – 3 Oct
5.0 out of 5 average rating, 29 reviews
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Top guest favourite
Flat in Simpson Bay, Sint Maarten
Apartment on the beach 2
Individual host
30 Sept – 5 Oct
4.86 out of 5 average rating, 208 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
21–26 Sept
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Flat in Cupecoy, Sint Maarten
Stunning oceanfront condo
2 bedrooms, 2 king beds, 2.5 bathrooms
28 Sept – 3 Oct
4.98 out of 5 average rating, 40 reviews
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Top guest favourite
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, 254 reviews
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Guest favourite
Flat in Simpson Bay, Sint Maarten
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 69 reviews
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Top guest favourite
Loft in Marigot, St Martin
Sea Loft, Breathtaking View – Private Pool
2 bedrooms, 2 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 202 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
8–13 Dec
5.0 out of 5 average rating, 84 reviews
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Top guest favourite
Room in Simpson Bay, Sint Maarten
Sanctuary near Maho: Tropical beach vacation stay!
Individual host
1–6 Oct
5.0 out of 5 average rating, 9 reviews