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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, 241 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
5.0 out of 5 average rating, 7 reviews
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Superhost
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
19–26 Sept
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Apartment in Longboat Key
Secluded Bayside Gem with beautiful bay views
2 bedrooms, 3 beds, 2 bathrooms
3–10 Oct
4.97 out of 5 average rating, 72 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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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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Guest favourite
Apartment in Longboat Key
2 Salty by Duncan Real Estate
1 bedroom, 1 king bed, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 5 reviews
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Flat in Longboat Key
Fantastic Beach Condo
3 bedrooms, 4 beds, 2 bathrooms
14–19 Jul
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Apartment in Sarasota
Downtown Sarasota Condo. Pool/Gym and Bay Views!
2 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
New place to stay
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Top guest favourite
Apartment in Bradenton Beach
Bayfront • Rehabbed • Pickleball • Private Beach
2 bedrooms, 3 beds, 2 bathrooms
19–26 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Sarasota
Sun Coast Oasis-Heated Pool-Pool Table-Arcade
3 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 9 reviews
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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
19–26 Sept
4.96 out of 5 average rating, 26 reviews
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Home in Longboat Key
An Oasis at Little Gull Cottages
1 bedroom, 2 beds, 1 bathroom
6–11 Mar
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Bradenton Beach
Beachfront Corner Condo | Sunset Gulf Views
1 bedroom, 2 beds, 1 bathroom
9–16 Nov
4.98 out of 5 average rating, 58 reviews
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Top guest favourite
Home in Bradenton Beach
Gulf Front! Sunset Deck! + Walk to Bridge St Pier!
3 bedrooms, 5 beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 128 reviews
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Top guest favourite
Home in Holmes Beach
NEW! w/ Pool - The Pearl Unit 2 on AMI
2 bedrooms, 2 beds, 1.5 bathrooms
20–27 Sept
5.0 out of 5 average rating, 11 reviews
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Apartment in Sarasota
Sarasota Designer Waterfront Retreat * Paddleboard
2 bedrooms, 2 beds, 1.5 bathrooms
22–29 Sept