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Search results; Over 1,000 homes in Longboat Key

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Guest favourite
Home in Longboat Key
Summer House longboat key
3 bedrooms, 6 beds, 3 private bathrooms
8–13 Oct
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4.86 out of 5 average rating, 143 reviews
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Guest favourite
Flat in Longboat Key
Beachfront Bliss | Walk to the Water- 104
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.56 out of 5 average rating, 9 reviews
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Casa particular in Longboat Key
Seaside Cottage Retreat Steps Away From the Beach
2 bedrooms, 4 beds, 2 bathrooms
2–7 Jan
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Longboat Key
Waterfront 2BR 2BA | Pool - 10 min walk to Beach
2 bedrooms, 3 beds, 2 bathrooms
1–8 Oct
5.0 out of 5 average rating, 15 reviews
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Guest favourite
Apartment in Longboat Key
2 Salty by Duncan Real Estate
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 5 reviews
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Superhost
Home in Longboat Key
Waterfront Oasis: Private Heated Pool + Fire Pit
2 bedrooms, 2 king beds, 2 bathrooms
15–20 Apr
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Superhost
Flat in Longboat Key
Sea Grape Inn#8- Beachfront Property
3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Oct
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Guest favourite
Home in Longboat Key
Private Island Beachfront Home
4 bedrooms, 10 beds, 4 bathrooms
1–8 Oct
4.96 out of 5 average rating, 26 reviews
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Top guest favourite
Apartment in Bradenton Beach
Steps to Beach on Anna Maria | 2 Pools & Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
14–19 Nov
4.95 out of 5 average rating, 22 reviews
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Guest favourite
Home in Bradenton
Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI
5 bedrooms, 6 beds, 3 bathrooms
27 Oct – 1 Nov
4.96 out of 5 average rating, 151 reviews
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Rooms in Longboat Key
Gulfside Getaway – Silver Sands Resort #235 by R
2 bedrooms, 4 beds, 2 bathrooms
16–21 Oct
5.0 out of 5 average rating, 4 reviews
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Home in Sarasota
*BRAND NEW* heated pool, golf course views
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
New place to stay
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Home in Longboat Key
Bayou and Beach Longboat Key Private Home
5 bedrooms, 6 beds, 4 bathrooms
21–26 Mar
5.0 out of 5 average rating, 4 reviews
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Apartment in Sarasota
Sarasota Designer Waterfront Retreat * Paddleboard
2 bedrooms, 2 beds, 1.5 bathrooms
1–8 Oct
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Superhost
Apartment in Longboat Key
Sea Grape Inn #6- Beachfront Property
2 bedrooms, 4 beds, 2 bathrooms
8–13 Oct
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Superhost
Home in Bradenton
Sauna • Cold Plunge • Sports Court • Pool • Hottub
4 bedrooms, 7 beds, 3 bathrooms
10–15 Oct
New place to stay
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Top guest favourite
Home in Holmes Beach
Best Location! Heated Pool~Steps to Beach/Shops!
1 bedroom, 1 king bed, 1 bathroom
1–6 Dec
4.95 out of 5 average rating, 42 reviews
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Top guest favourite
Apartment in Bradenton Beach
Bayfront • Rehabbed • Pickleball • Private Beach
2 bedrooms, 3 beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Bradenton
Pool, Hot Tub, PickleBall, Firepit, 5 min to IMG
4 bedrooms, 5 beds, 3.5 bathrooms
2–7 Oct
5.0 out of 5 average rating, 11 reviews