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Search results; Over 1,000 homes in Simpson Bay

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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 beds, 3 private bathrooms
1–6 Oct
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4.92 out of 5 average rating, 26 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
1–6 Oct
4.97 out of 5 average rating, 29 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
1–6 Oct
4.95 out of 5 average rating, 21 reviews
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Guest favourite
Flat in Simpson Bay, Sint Maarten
Villa Harmony Haven
3 bedrooms, 3 king beds
1–6 Oct
5.0 out of 5 average rating, 69 reviews
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Guest favourite
Serviced apartment in Simpson Bay, Sint Maarten
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds
1–6 Oct
4.94 out of 5 average rating, 32 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
25–30 Oct
4.98 out of 5 average rating, 95 reviews
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Guest favourite
Serviced apartment in Simpson Bay, Sint Maarten
Unit 3 - Luxury apartment by the sea
1 bedroom, 2 beds
5–10 Oct
4.85 out of 5 average rating, 55 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
10–15 Oct
5.0 out of 5 average rating, 29 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
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
1–6 Oct
4.95 out of 5 average rating, 113 reviews
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Home in Cole Bay, Sint Maarten
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 61 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
7–12 Oct
4.92 out of 5 average rating, 12 reviews
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Guest favourite
Flat in Maho Beach, Sint Maarten
Escapes at the Emerald – Airport & Beach Nearby
1 queen bed
20–25 Feb
4.93 out of 5 average rating, 28 reviews
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Guest favourite
Apartment in Simpson Bay, Sint Maarten
1 Bedroom Seafront Flat D3
1 bedroom, 1 bed
1–6 Oct
5.0 out of 5 average rating, 18 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
1–6 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds
8–13 Dec
5.0 out of 5 average rating, 45 reviews
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Top guest favourite
Apartment in Maho, Sint Maarten
Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub
1 bedroom, 1 queen bed
1–6 Oct
4.91 out of 5 average rating, 259 reviews
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Guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
2 beds
1–6 Oct
5.0 out of 5 average rating, 85 reviews
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Top guest favourite
Flat in Grand Cayes, St Martin
Modern Sea View Apartment from Pinel island
1 bedroom, 1 queen bed
2–7 Oct
5.0 out of 5 average rating, 38 reviews