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Search results; Over 1,000 homes in Simpson Bay

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Top guest favourite
Apartment in Simpson Bay
The Beach Condo
2 bedrooms, 2 beds, 2.5 private bathrooms
16–21 Sept
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4.99 out of 5 average rating, 83 reviews
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Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 69 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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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
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
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds, 3 bathrooms
9–14 Nov
4.99 out of 5 average rating, 336 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
16–21 Sept
4.95 out of 5 average rating, 109 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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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, 77 reviews
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Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
23–28 Dec
5.0 out of 5 average rating, 84 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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Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds, 3.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 45 reviews
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Guest favourite
Flat in Simpson Bay
Unit 7 - Luxury apartment by the sea
1 bedroom, 1 king bed, 1 bathroom
16–21 Sept
4.93 out of 5 average rating, 80 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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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
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds, 2 bathrooms
3–8 Nov
4.99 out of 5 average rating, 105 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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Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds, 5.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 29 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
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