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Search results; Over 1,000 homes in Simpson Bay

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Guest favourite
Apartment in Simpson Bay
Paradiso - 2 bedroom Condo steps to Cupecoy Beach!
2 bedrooms, 2 beds, 2.5 private bathrooms
1–6 Oct
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5.0 out of 5 average rating, 11 reviews
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Guest favourite
Apartment in Simpson Bay
Five Star Luxury Beachfront Condo Private Hot Tub
2 bedrooms, 2 king beds, 2.5 bathrooms
3–8 Oct
4.94 out of 5 average rating, 88 reviews
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Top guest favourite
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds, 3 bathrooms
25–30 Oct
4.99 out of 5 average rating, 339 reviews
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Top guest favourite
Place to stay in Simpson Bay
Your floating B&B at SXM
Individual host
2–7 Dec
5.0 out of 5 average rating, 29 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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Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
1 bedroom, 1 king bed, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 254 reviews
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Guest favourite
Hotel room in Simpson Bay
Azure Beach Hotel Tiki Suite
1 bedroom, 1 double bed, 1 bathroom
11–16 Oct
4.84 out of 5 average rating, 154 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
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
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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Top guest favourite
Apartment in Upper Prince's Quarter
Serenity Seascape | 2BR Retreat, 270° Oceanviews
2 bedrooms, 2 king beds, 2.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 11 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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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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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
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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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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Top guest favourite
Flat in Simpson Bay
Vitamin sea 2
1 bedroom, 1 bed, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 29 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
10–15 Oct
4.97 out of 5 average rating, 38 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