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Search results; Over 1,000 homes in Longboat Key

Top guest favorite
Condo in Longboat Key
The Beach Condo #107 Beachfront Full View
Studio, 2 beds, 1 private bath
Aug 16 – 21
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4.87 out of 5 average rating, 209 reviews
Superhost
Casa particular in Longboat Key
Seaside Cottage Retreat Steps Away From the Beach
2 bedrooms, 4 beds, 2 baths
Aug 12 – 19
5.0 out of 5 average rating, 3 reviews
Home in Longboat Key
Artists Retreat, walk to the beach
2 bedrooms, 2 beds, 1 bath
Aug 12 – 19
5.0 out of 5 average rating, 4 reviews
Top guest favorite
Apartment in Longboat Key
Waterfront 2BR 2BA | Pool - 10 min walk to Beach
2 bedrooms, 3 beds, 2 baths
Sep 15 – 22
5.0 out of 5 average rating, 14 reviews
Superhost
Condo in Longboat Key
2 Salty by Duncan Real Estate
1 bedroom, 1 king bed, 1 bath
Aug 12 – 17
5.0 out of 5 average rating, 4 reviews
Top guest favorite
Apartment in Bradenton Beach
Beachfront Corner Condo | Sunset Gulf Views
1 bedroom, 2 beds, 1 bath
Oct 10 – 15
4.98 out of 5 average rating, 53 reviews
Guest favorite
Home in Holmes Beach
Pineapple Paradise | Private Pool | Walk to Beach
2 bedrooms, 6 beds, 2 baths
Aug 16 – 23
5.0 out of 5 average rating, 14 reviews
Top guest favorite
Home in Anna Maria
Bean Pt. Bungalow - Half duplex w/private pool
3 bedrooms, 6 beds, 2 baths
Aug 23 – 28
5.0 out of 5 average rating, 105 reviews
Superhost
Home in Sarasota
Sun Coast Oasis-Heated Pool-Pool Table-Arcade
3 bedrooms, 5 beds, 2 baths
Sep 9 – 14
5.0 out of 5 average rating, 4 reviews
Top guest favorite
Home in Bradenton
The Florida Rooms
3 bedrooms, 3 beds, 2 baths
Oct 26 – 31
4.96 out of 5 average rating, 45 reviews
Top guest favorite
Home in Bradenton
Heated Pool, 5 miles to the Beach, Sleeps 8
3 bedrooms, 5 beds, 2 baths
Oct 22 – 27
4.97 out of 5 average rating, 66 reviews
Top guest favorite
Condo in Bradenton Beach
Bayfront • Rehabbed • Pickleball • Private Beach
2 bedrooms, 3 beds, 2 baths
Aug 25 – Sep 1
5.0 out of 5 average rating, 8 reviews
Top guest favorite
Home in Bradenton Beach
Walk to it all! Restaurants + Heated Pool +Beach!
3 bedrooms, 7 beds, 3 baths
Aug 14 – 19
4.98 out of 5 average rating, 111 reviews
Top guest favorite
Home in Sarasota
Modern 4BR Home *Heated Pool & Spa*
4 bedrooms, 4 beds, 2 baths
Sep 7 – 12
4.95 out of 5 average rating, 197 reviews
Superhost
Home in Longboat Key
Waterfront Oasis: Private Heated Pool + Fire Pit
2 bedrooms, 2 king beds, 2 baths
Apr 15 – 20
Guest favorite
Home in Bradenton Beach
Bradenton Beach Getaway | Steps to Sand & Dining
2 bedrooms, 3 beds, 2 baths
Aug 16 – 21
5.0 out of 5 average rating, 7 reviews
Guest favorite
Home in Bradenton
New! Pickleball, Heated Pool, Game Room, Fire Pit
4 bedrooms, 6 beds, 2 baths
Aug 24 – 29
5.0 out of 5 average rating, 9 reviews
Rooms in Longboat Key
Gulfside Getaway – Silver Sands Resort #235 by R
2 bedrooms, 4 beds, 2 baths
Aug 20 – 25
5.0 out of 5 average rating, 4 reviews
Top guest favorite
Home in Bradenton
Heated Salt Pool•Mini Golf•Arcade•Spa•AMI 6mi•IMG
3 bedrooms, 5 beds, 2 baths
Aug 23 – 28
5.0 out of 5 average rating, 86 reviews