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Search results; Over 1,000 homes in Longboat Key

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Top guest favourite
Apartment in Longboat Key
Beachfront Resort, Ocean View, Pool, Tennis, Gym
1 bedroom, 2 beds, 1 private bathroom
26–31 Oct
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4.9 out of 5 average rating, 243 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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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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Flat in Longboat Key
Sea Grape Inn#8- Beachfront Property
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Oct
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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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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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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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Apartment in Sarasota
Sarasota Designer Waterfront Retreat * Paddleboard
2 bedrooms, 2 beds, 1.5 bathrooms
1–8 Oct
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Room in Longboat Key
Oceanfront Oasis – Longboat Key 226 by RVA
2 beds, 1 bathroom
15–20 Oct
4.67 out of 5 average rating, 6 reviews
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Apartment in Longboat Key
Sea Grape Inn #6- Beachfront Property
2 bedrooms, 4 beds, 2 bathrooms
8–13 Oct
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Top guest favourite
Flat in Bradenton Beach
Beachfront Corner Condo | Sunset Gulf Views
1 bedroom, 2 beds, 1 bathroom
9–14 Nov
4.98 out of 5 average rating, 59 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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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, 152 reviews
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Home in Bradenton Beach
Beachfront · Heated Pool & Spa · Balcony Views
4 bedrooms, 5 beds, 4 bathrooms
25–30 Oct
New place to stay
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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, 12 reviews
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Superhost
Home in Bradenton
NEW! Sleeps 12~Heated pool~Sauna~Gym~Games~Bar
3 bedrooms, 8 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Apartment in Bradenton Beach
Largest Pool • Private Beach Access • Pickleball
2 bedrooms, 3 beds, 2 bathrooms
4–11 Oct
5.0 out of 5 average rating, 17 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