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Search results; Over 1,000 homes in Simpson Bay

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Top guest favourite
Guest suite in Simpson Bay
Fig Paradis Penthouse
1 bedroom, 2 beds, 1 private bathroom
12–17 Oct, Individual host
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4.98 out of 5 average rating, 82 reviews
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Guest favourite
Apartment in Simpson Bay
Hamaka condo, a beachfront retreat on Simpson Bay
Business host
25–30 Sept
4.95 out of 5 average rating, 106 reviews
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Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 king beds, 2.5 bathrooms
10–15 Mar
4.96 out of 5 average rating, 109 reviews
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Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 69 reviews
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Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Middle Floor - Unit 2
3 bedrooms, 3 beds, 3.5 bathrooms
18–23 Sept
4.97 out of 5 average rating, 38 reviews
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Top guest favourite
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds, 3 bathrooms
21–26 Nov
4.99 out of 5 average rating, 337 reviews
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Top guest favourite
Villa in Simpson Bay
Waterfront "Bonjour" Beacon Hill St Maarten
4 bedrooms, 4 king beds, 4 bathrooms
18–23 Oct
4.97 out of 5 average rating, 92 reviews
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Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
23–28 Sept
4.91 out of 5 average rating, 58 reviews
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Top guest favourite
Guest house in Simpson Bay
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 queen bed, 1 bathroom
18–23 Sept
4.95 out of 5 average rating, 109 reviews
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Guest favourite
Flat in Simpson Bay
Top of the art penthouse
3 bedrooms, 4 beds, 3.5 bathrooms
1–6 Oct
4.95 out of 5 average rating, 113 reviews
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Guest favourite
Townhouse in Simpson Bay
Utopia A3 | Beachside Stay @ The Drake Residences
2 bedrooms, 3 beds, 2.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 8 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
29 Sept – 4 Oct
4.96 out of 5 average rating, 113 reviews
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Guest favourite
Flat in Simpson Bay
Private Pool- 5 min DRIVE to Maho Beach & Airport
1 bedroom, 1 queen bed, 1 bathroom
28 Sept – 3 Oct
4.96 out of 5 average rating, 78 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
18–23 Sept
5.0 out of 5 average rating, 29 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
Villa in Koolbaai
Sol y Mar - Beachfront Penthouse with private pool
3 bedrooms, 4 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 18 reviews
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Home in Koolbaai
Villa Where Dreams Meet the Sea
2 bedrooms, 2 king beds, 2.5 bathrooms
18–23 Sept
New place to stay
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Top guest favourite
Home in Koolbaai
Pelican key - BEACH FRONT Villa
Individual host
27 Sept – 2 Oct
5.0 out of 5 average rating, 48 reviews
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Top guest favourite
Flat in Simpson Bay
Apartment on the beach 2
Individual host
30 Sept – 5 Oct
4.86 out of 5 average rating, 208 reviews