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Search results; Over 1,000 homes in Simpson Bay

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Superhost
Apartment in Simpson Bay
Oceanfront w Pool | Maho Beach area
1 bedroom, 2 beds, 1.5 private bathrooms
24–30 Sept
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4.8 out of 5 average rating, 192 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
Flat in Simpson Bay
SeaBliss 3BR Palm Beach Condo Simpson Bay
3 bedrooms, 3 beds, 3 bathrooms
25–30 Sept
4.98 out of 5 average rating, 42 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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Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 69 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
19–24 Sept
4.93 out of 5 average rating, 80 reviews
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Guest favourite
Flat in Simpson Bay
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.94 out of 5 average rating, 32 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
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
Flat in Simpson Bay
Apartment on the beach 2
Individual host
30 Sept – 5 Oct
4.86 out of 5 average rating, 208 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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Guest favourite
Flat in Simpson Bay
2BR Escape - Walk to Maho and Simpson Bay Beach
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
4.9 out of 5 average rating, 31 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
19–24 Sept
4.95 out of 5 average rating, 109 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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Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds, 5.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 29 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 Sint Maarten
Indigo Oceanfront Condo Poolside - Unit 1
3 bedrooms, 3 beds, 3.5 bathrooms
28 Sept – 3 Oct
4.98 out of 5 average rating, 48 reviews
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Guest favourite
Flat in Simpson Bay
Unit 3 - Luxury apartment by the sea
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
4.85 out of 5 average rating, 55 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
20–25 Sept
5.0 out of 5 average rating, 24 reviews