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Search results; Over 1,000 homes in Simpson Bay

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Top guest favourite
Flat in Simpson Bay
Lilly's Beach
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
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4.95 out of 5 average rating, 247 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
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 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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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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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
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
Villa in Simpson Bay
Surfsong Villa- Luxury Water Front Villa for 12
6 bedrooms, 6 king beds, 6 bathrooms
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
8–13 Oct
4.86 out of 5 average rating, 145 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
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
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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Guest favourite
Apartment in Little Bay
Maazoon -Luxury modern 3BR Apt for 6 – Central SXM
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.95 out of 5 average rating, 21 reviews
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Top guest favourite
Townhouse in Sint Maarten
Indigo Bay Villa Poolside - Ocean 14
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Oct
4.96 out of 5 average rating, 113 reviews
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Townhouse in Simpson Bay
The Drake's "Suite Serenity" @ White Sands Villas
3 bedrooms, 7 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Hotel in Upper Prince's Quarter
1BR Luxury Apartment | Ocean View
1 bedroom, 1 king bed, 1.5 bathrooms
1–6 Oct
4.92 out of 5 average rating, 25 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