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Search results; Over 1,000 homes in Simpson Bay

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Top guest favourite
Holiday home in Simpson Bay, Sint Maarten
High-end Waterfront 2-Bed Condo
2 bedrooms, 2 beds, 1.5 private bathrooms
18–23 Oct
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5.0 out of 5 average rating, 12 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, 4 bathrooms
20–25 Sept
4.97 out of 5 average rating, 29 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
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
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
Home in Cole Bay, Sint Maarten
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 61 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
22–27 Sept
4.95 out of 5 average rating, 20 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, 6 bathrooms
20–25 Sept
4.98 out of 5 average rating, 95 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 king beds, 3 bathrooms
21–26 Sept
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Room in Simpson Bay, Sint Maarten
Sanctuary near Maho: Tropical beach vacation stay!
1 double bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 9 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, 3.5 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 21 reviews
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Top guest favourite
Home in Koolbaai, Sint Maarten
Pelican key - BEACH FRONT Villa
3 bedrooms, 5 beds, 3.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 48 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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Superhost
Flat in Maho Beach, Sint Maarten
Turtle Den YOUR Maho Escape!
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.86 out of 5 average rating, 145 reviews
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Flat in Lowlands, Sint Maarten
Maison Douma | Blue Marine | Near Maho & Beaches
1 bedroom, 2 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 3 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
Serviced apartment in Simpson Bay, Sint Maarten
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.94 out of 5 average rating, 32 reviews
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Top guest favourite
Apartment in Simpson Bay, Sint Maarten
The Beach Condo
2 bedrooms, 2 king beds, 2.5 bathrooms
20–25 Sept
4.99 out of 5 average rating, 83 reviews
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Guest favourite
Flat in Lowlands, Sint Maarten
Luxury Maho Studio|Walk to Beach|5 mins to Airport
1 bedroom, 1 queen bed, 1 bathroom
23–28 Sept
4.92 out of 5 average rating, 12 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