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Search results; Over 1,000 homes in Simpson Bay

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Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 beds, 2.5 private bathrooms
10–15 Mar
,
4.96 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
1–6 Oct
5.0 out of 5 average rating, 86 reviews
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Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds, 4 bathrooms
1–6 Oct
4.97 out of 5 average rating, 29 reviews
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Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 69 reviews
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Guest favourite
Flat in Simpson Bay
SeaHarmony 3BR Palm Beach Condo in Simpson Bay
3 bedrooms, 3 king beds, 3.5 bathrooms
1–6 Oct
4.95 out of 5 average rating, 21 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
10–15 Oct
5.0 out of 5 average rating, 29 reviews
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Guest favourite
Serviced apartment in Simpson Bay
Unit 3 - Luxury apartment by the sea
1 bedroom, 2 beds, 1 bathroom
5–10 Oct
4.85 out of 5 average rating, 55 reviews
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Guest favourite
Apartment in Simpson Bay
Hamaka condo, a beachfront retreat on Simpson Bay
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.95 out of 5 average rating, 106 reviews
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Top guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 61 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
Apartment in Simpson Bay
1 Bedroom Seafront Flat D3
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Serviced apartment in Simpson Bay
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.94 out of 5 average rating, 32 reviews
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Guest favourite
Flat in Maho Beach
Escapes at the Emerald – Airport & Beach Nearby
1 queen bed, 1 bathroom
20–25 Feb
4.93 out of 5 average rating, 28 reviews
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Top guest favourite
Apartment in Simpson Bay
The Penthouse at LaSiesta - 3 BD - Luxury Awaits!
3 bedrooms, 3 king beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 14 reviews
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Flat in Pelican Key
Gorgeous Beach Loft with Sweeping Ocean Views
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
New place to stay
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Guest favourite
Flat in Lowlands
Luxury Maho Studio|Walk to Beach|5 mins to Airport
1 bedroom, 1 queen bed, 1 bathroom
7–12 Oct
4.92 out of 5 average rating, 12 reviews
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Flat in Lowlands
Maison Douma | Blue Marine | Near Maho & Beaches
1 bedroom, 2 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Villa in Lowlands
SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay
3 bedrooms, 3 king beds, 3.5 bathrooms
5–10 Oct
4.77 out of 5 average rating, 154 reviews
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Top guest favourite
Apartment in Maho
Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
4.91 out of 5 average rating, 260 reviews