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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
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 bed, 1 private bathroom
1–6 Sept
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4.95 out of 5 average rating, 109 reviews
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Guest favourite
Flat in Simpson Bay
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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Hotel room in Simpson Bay
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
24–29 Sept
4.87 out of 5 average rating, 271 reviews
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Flat in Simpson Bay
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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Flat in Simpson Bay
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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Guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
Individual host
13–18 Sept
4.96 out of 5 average rating, 26 reviews
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Guest favourite
Villa in Simpson Bay
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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Flat in Simpson Bay
Unit 7 - Luxury apartment by the sea
1 bedroom, 1 king bed, 1 bathroom
16–21 Sept
4.93 out of 5 average rating, 80 reviews
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Home in Koolbaai
Waterfront paradise facing the ocean SXM
Individual host
1–6 Sept
New place to stay
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Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
1 bedroom, 1 king bed, 1.5 bathrooms
24–29 Sept
5.0 out of 5 average rating, 252 reviews
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Home in Koolbaai
Pelican key - BEACH FRONT Villa
Individual host
27 Sept – 2 Oct
5.0 out of 5 average rating, 47 reviews
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Flat in Simpson Bay
Apartment on the beach 2
Individual host
11–16 Sept
4.85 out of 5 average rating, 206 reviews
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Apartment in Maho
Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
4.91 out of 5 average rating, 257 reviews
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Flat in Simpson Bay
Second Home Beach Apartment
Individual host
20–25 Sept
4.99 out of 5 average rating, 106 reviews
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Flat in Maho Beach
Escapes at the Emerald – Airport & Beach Nearby
Individual host
16–21 Nov
4.92 out of 5 average rating, 25 reviews
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Top guest favourite
Apartment in Simpson Bay
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
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 60 reviews
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Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Poolside - Unit 1
3 bedrooms, 3 beds, 3.5 bathrooms
3–8 Oct
4.98 out of 5 average rating, 46 reviews
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Flat in Simpson Bay
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.94 out of 5 average rating, 32 reviews