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Search results; Over 1,000 homes in Simpson Bay

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Top guest favourite
Holiday home in Simpson Bay, Sint Maarten
High-end Waterfront 2-Bed Condo
2 bedrooms, 2 beds, 1.5 private bathrooms
18–23 Oct
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5.0 out of 5 average rating, 12 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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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
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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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
Hotel room in Simpson Bay, Sint Maarten
Azure Hotel Bay Suite
1 bedroom, 1 single bed
31 Oct – 5 Nov
4.87 out of 5 average rating, 275 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
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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Top guest favourite
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
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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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
Apartment in Simpson Bay, Sint Maarten
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds
1–6 Oct
4.92 out of 5 average rating, 26 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
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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Superhost
Flat in Maho Beach, Sint Maarten
Turtle Den YOUR Maho Escape!
1 bedroom, 1 queen bed
8–13 Oct
4.86 out of 5 average rating, 145 reviews
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Top guest favourite
Townhouse in Sint Maarten, Sint Maarten
Indigo Bay Villa Poolside - Ocean 14
2 bedrooms, 2 king beds
1–6 Oct
4.96 out of 5 average rating, 113 reviews
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Townhouse in Simpson Bay, Sint Maarten
The Drake's "Suite Serenity" @ White Sands Villas
3 bedrooms, 7 beds
4–9 Oct
5.0 out of 5 average rating, 4 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
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and pool access
3 bedrooms, 3 king beds
15–20 Oct
5.0 out of 5 average rating, 10 reviews