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Search results; Over 1,000 homes in Simpson Bay

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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 bed, 1 private bathroom
19–24 Sept
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4.95 out of 5 average rating, 109 reviews
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Top guest favourite
Apartment in Simpson Bay, Sint Maarten
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds
20–25 Sept
4.97 out of 5 average rating, 29 reviews
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Guest favourite
Flat in Simpson Bay, Sint Maarten
Villa Harmony Haven
3 bedrooms, 3 king beds
20–25 Sept
5.0 out of 5 average rating, 69 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
28 Sept – 3 Oct
4.96 out of 5 average rating, 78 reviews
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Guest favourite
Flat in Simpson Bay, Sint Maarten
SeaHarmony 3BR Palm Beach Condo in Simpson Bay
3 bedrooms, 3 king beds
19–24 Sept
4.95 out of 5 average rating, 21 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
1–6 Oct
4.92 out of 5 average rating, 26 reviews
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Guest favourite
Serviced apartment in Simpson Bay, Sint Maarten
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds
21–26 Sept
4.94 out of 5 average rating, 32 reviews
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Top guest favourite
Home in Cole Bay, Sint Maarten
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 61 reviews
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Top guest favourite
Villa in Simpson Bay, Sint Maarten
Surfsong Villa- Luxury Water Front Villa for 12
6 bedrooms, 6 king beds
20–25 Sept
4.98 out of 5 average rating, 95 reviews
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Top guest favourite
Apartment in Simpson Bay, Sint Maarten
The Beach Condo
2 bedrooms, 2 king beds
19–24 Sept
4.99 out of 5 average rating, 83 reviews
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Top guest favourite
Home in Koolbaai, Sint Maarten
Pelican key - BEACH FRONT Villa
3 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 48 reviews
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Guest favourite
Apartment in Simpson Bay, Sint Maarten
Hamaka condo, a beachfront retreat on Simpson Bay
1 bedroom, 2 beds
25–30 Sept
4.95 out of 5 average rating, 106 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
20–25 Sept
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Flat in Simpson Bay, Sint Maarten
TropiCasa - Watch sunsets surf the waves, 1BR
1 bedroom, 1 bed
1–6 Oct
5.0 out of 5 average rating, 16 reviews
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Guest favourite
Townhouse in Simpson Bay, Sint Maarten
Utopia A3 | Beachside Stay @ The Drake Residences
2 bedrooms, 3 beds
19–24 Sept
5.0 out of 5 average rating, 8 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
19–24 Sept
5.0 out of 5 average rating, 29 reviews
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Top guest favourite
Flat in Grand-Case, St Martin
Beachfront Luxury Suite with Sea View Grand Case
2 bedrooms, 2 king beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 36 reviews
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Guest favourite
Flat in Grand-Case, St Martin
Unmatched Oceanfront Living in Grand Case
2 bedrooms, 2 beds
21–26 Sept
4.89 out of 5 average rating, 28 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
22–27 Sept
4.95 out of 5 average rating, 20 reviews