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Search results; Over 1,000 homes in Longboat Key

Guest favourite
Cottage in Longboat Key
Bayside Bliss: 1BR Cottage on Longboat Key
1 bedroom, 2 beds, 1 private bathroom
19–26 Dec
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5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Longboat Key
Beachfront Bliss | Walk to the Water- 104
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 5 reviews
Home in Longboat Key
Artists Retreat, walk to the beach
2 bedrooms, 2 beds, 1 bathroom
2–9 Sept
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 bathrooms
2–9 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Longboat Key
Waterfront 2BR 2BA | Pool - 10 min walk to Beach
2 bedrooms, 3 beds, 2 bathrooms
15–22 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Apartment in Longboat Key
Secluded Bayside Gem with beautiful bay views
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 72 reviews
Superhost
Home in Longboat Key
Waterfront Oasis: Private Heated Pool + Fire Pit
2 bedrooms, 2 king beds, 2 bathrooms
15–20 Apr
Guest favourite
Home in Longboat Key
Private Island Beachfront Home
4 bedrooms, 10 beds, 4 bathrooms
2–9 Sept
4.96 out of 5 average rating, 26 reviews
Flat in Longboat Key
Fantastic Beach Condo
3 bedrooms, 4 beds, 2 bathrooms
14–19 Jul
Top guest favourite
Home in Holmes Beach
Best deal of year starts 8/29~Pool~Steps to beach!
3 bedrooms, 4 beds, 3 bathrooms
2–9 Sept
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Apartment in Holmes Beach
#terraceLIFE | 2 Blocks to Beach | Heated Pool
2 bedrooms, 4 beds, 2 bathrooms
9–16 Sept
4.88 out of 5 average rating, 112 reviews
Superhost
Apartment in Longboat Key
2 Salty by Duncan Real Estate
1 bedroom, 1 king bed, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Bradenton Beach
Gulf Front! Sunset Deck! + Walk to Bridge St Pier!
3 bedrooms, 5 beds, 1 bathroom
14–19 Sept
4.98 out of 5 average rating, 125 reviews
Superhost
Apartment in Longboat Key
Sea Grape Inn #6- Beachfront Property
2 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
Superhost
Flat in Longboat Key
Sea Grape Inn#8- Beachfront Property
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
Top guest favourite
Apartment in Siesta Key
Private Beach•3 Heated Pools•2BR•Ground Floor
2 bedrooms, 3 beds, 2 bathrooms
28 Nov – 3 Dec
5.0 out of 5 average rating, 7 reviews
Home in Longboat Key
Lovely townhouse on Sarasota Bay
2 bedrooms, 3 beds, 2.5 bathrooms
9–14 Sept
Top guest favourite
Home in Bradenton
The Blue Marlin
3 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 16 reviews
Apartment in Sarasota
Sarasota Designer Waterfront Retreat * Paddleboard
2 bedrooms, 2 beds, 1.5 bathrooms
4–11 Sept
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