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Search results; Over 1,000 homes in Longboat Key

Top guest favorite
Apartment in Longboat Key
Longboat Key-OCEAN FRONT- on the beach
2 bedrooms, 3 beds, 2 private baths
Sep 26 – Oct 1
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4.96 out of 5 average rating, 124 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
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
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
Top guest favorite
Condo in Longboat Key
Secluded Bayside Gem with beautiful bay views
2 bedrooms, 3 beds, 2 baths
Aug 22 – 29
4.97 out of 5 average rating, 72 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
Superhost
Home in Longboat Key
Waterfront Oasis: Private Heated Pool + Fire Pit
2 bedrooms, 2 king beds, 2 baths
Apr 15 – 20
Apartment in Longboat Key
Fantastic Beach Condo
3 bedrooms, 4 beds, 2 baths
Jul 14 – 19
Home in Holmes Beach
Bayfront Home:Dock, Heated Pool, Manatees
4 bedrooms, 6 beds, 3 baths
Aug 29 – Sep 5
5.0 out of 5 average rating, 3 reviews
Superhost
Apartment in Longboat Key
Sea Grape Inn#8- Beachfront Property
3 bedrooms, 4 beds, 2.5 baths
Aug 17 – 22
Home in Longboat Key
Lovely townhouse on Sarasota Bay
2 bedrooms, 3 beds, 2.5 baths
Aug 12 – 17
Top guest favorite
Townhouse in Holmes Beach
Townhouse 200 Steps to the Beach
2 bedrooms, 3 beds, 1.5 baths
Aug 14 – 21
5.0 out of 5 average rating, 27 reviews
Superhost
Condo in Longboat Key
Sea Grape Inn #6- Beachfront Property
2 bedrooms, 4 beds, 2 baths
Aug 12 – 17
Luxe
Home in Bradenton Beach
Dream State ~ Gulf Front/Across from Beach!
6 bedrooms, 7 beds, 5.5 baths
Aug 30 – Sep 4
5.0 out of 5 average rating, 22 reviews
Guest favorite
Home in Longboat Key
Private Island Beachfront Home
4 bedrooms, 10 beds, 4 baths
Aug 12 – 19
4.96 out of 5 average rating, 25 reviews
Top guest favorite
Condo in Holmes Beach
#terraceLIFE | 2 Blocks to Beach | Heated Pool
2 bedrooms, 4 beds, 2 baths
Aug 30 – Sep 6
4.88 out of 5 average rating, 110 reviews
Top guest favorite
Home in Sarasota
Siesta Serenity ~ Pool/Waterslide/Waterfront
4 bedrooms, 5 beds, 4 baths
Aug 30 – Sep 4
5.0 out of 5 average rating, 21 reviews
Top guest favorite
Home in Holmes Beach
Seaquel A Tropical Retreat - Private Pool Home
3 bedrooms, 3 beds, 2 baths
Aug 31 – Sep 7
5.0 out of 5 average rating, 8 reviews
Condo in Longboat Key
Harbor Villa Club 206 : Where Fun Meets Relaxation
2 bedrooms, 3 beds, 2 baths
Jan 9 – 16