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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
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
17–22 Oct
4.91 out of 5 average rating, 58 reviews
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Guest favourite
Apartment in Simpson Bay
Hamaka condo, a beachfront retreat on Simpson Bay
Business host
1–6 Oct
4.95 out of 5 average rating, 106 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, 85 reviews
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Guest favourite
Hotel room in Simpson Bay
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
31 Oct – 5 Nov
4.87 out of 5 average rating, 275 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, 259 reviews
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Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
Individual host
1–6 Oct
4.97 out of 5 average rating, 29 reviews
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Guest favourite
Flat 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
Individual host
20–25 Feb
4.93 out of 5 average rating, 28 reviews
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Guest favourite
Apartment in Simpson Bay
SeaShores Beach Front 1 Brm Apt With Generator SXM
1 bedroom, 2 beds, 1 bathroom
20–25 Oct
4.95 out of 5 average rating, 58 reviews
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Top guest favourite
Villa in Simpson Bay
Surfsong Villa- Luxury Water Front Villa for 12
Business host
25–30 Oct
4.98 out of 5 average rating, 95 reviews
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Superhost
Flat in Maho Beach
Turtle Den YOUR Maho Escape!
1 bedroom, 1 queen bed, 1 bathroom
29 Oct – 3 Nov
4.86 out of 5 average rating, 145 reviews
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Guest favourite
Apartment in Simpson Bay
SeaViews 2Brm Ocean Front Condo SXM
2 bedrooms, 2 beds, 2 bathrooms
1–6 Oct
4.92 out of 5 average rating, 36 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 Cole Bay
B224 - Amazing Lagoon-View Apartment with Balcony
1 bedroom, 2 beds, 1 bathroom
10–15 Oct
4.82 out of 5 average rating, 11 reviews
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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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Top guest favourite
Flat in Simpson Bay
TropiCasa - Watch sunsets surf the waves, 1BR
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds, 3.5 bathrooms
8–13 Dec
5.0 out of 5 average rating, 45 reviews
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Guest favourite
Apartment in Simpson Bay
1 Bedroom Seafront Flat D3
Individual host
1–6 Oct
5.0 out of 5 average rating, 18 reviews