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Search results; Over 1,000 homes in Simpson Bay

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Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 beds, 2.5 private bathrooms
10–15 Mar
,
4.96 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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Top guest favourite
Room in Simpson Bay
Sanctuary near Maho: Tropical beach vacation stay!
Individual host
1–6 Oct
5.0 out of 5 average rating, 9 reviews
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Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
8–13 Dec
5.0 out of 5 average rating, 84 reviews
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Top guest favourite
Flat in Simpson Bay
Simpson bay beach, spacious, beautiful views!
3 bedrooms, 3 king beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 157 reviews
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Guest favourite
Flat in Simpson Bay
2BR Escape - Walk to Maho and Simpson Bay Beach
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 31 reviews
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Top guest favourite
Villa in Simpson Bay
Surfsong Villa- Luxury Water Front Villa for 12
Business host
20–25 Sept
4.98 out of 5 average rating, 95 reviews
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Townhouse in Simpson Bay
"Suite Serenity" @ White Sands Villas
3 bedrooms, 6 beds, 3 bathrooms
19–24 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
Individual host
20–25 Sept
4.97 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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Superhost
Apartment in Simpson Bay
Maho Beach Oceanfront Getaway
1 bedroom, 2 beds, 1 bathroom
28 Sept – 3 Oct
4.67 out of 5 average rating, 231 reviews
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Top guest favourite
Flat in Simpson Bay
TropiCasa - Watch sunsets surf the waves, 1BR
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Apartment in Simpson Bay
The Beach Condo
2 bedrooms, 2 king beds, 2.5 bathrooms
18–23 Sept
4.99 out of 5 average rating, 83 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
18–23 Sept
4.93 out of 5 average rating, 80 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
19–24 Sept
5.0 out of 5 average rating, 24 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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Top guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 61 reviews
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Guest favourite
Apartment in Simpson Bay
SeaShores Beach Front 1 Brm Apt With Generator SXM
1 bedroom, 2 beds, 1 bathroom
20–25 Oct
4.95 out of 5 average rating, 58 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