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Search results; Over 1,000 homes in Longboat Key

Top guest favourite
Apartment in Longboat Key
Island Time: Open August 16th - 25th!
Studio, 2 beds, 1 private bathroom
16–21 Aug
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4.98 out of 5 average rating, 244 reviews
Superhost
Casa particular in Longboat Key
Seaside Cottage Retreat Steps Away From the Beach
2 bedrooms, 4 beds, 2 bathrooms
29 Jul – 5 Aug
Top guest favourite
Home in Longboat Key
Canal-Front Charmer with Private Beach Access!
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 6 beds, 2 bathrooms
26–31 Jul
Superhost
Apartment in Longboat Key
2 Salty by Duncan Real Estate
New place to stay, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Superhost
Home in Longboat Key
Waterfront Oasis: Private Heated Pool + Fire Pit
2 bedrooms, 2 beds, 2 bathrooms
15–20 Apr
Top guest favourite
Flat in Longboat Key
Waterfront 2BR 2BA | Pool - 10 min walk to Beach
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–8 Sept
Guest favourite
Home in Longboat Key
Private Island Beachfront Home
4.96 out of 5 average rating, 25 reviews, 4 bedrooms, 10 beds, 4 bathrooms
17–24 Jul
Home in Holmes Beach
TieDyeSky: Waterfall Pool, Steps 2 Beach, Elevator
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 7 beds, 3 bathrooms
21–28 Aug
Top guest favourite
Home in Cortez
Beach Retreat! Paddleboards, Bikes, & Beach Gear!
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Jul
Guest favourite
Home in Siesta Key
House on Siesta Key with Private Pool and Hot tub!
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 4 beds, 4 bathrooms
24–29 Aug
Top guest favourite
Home in Anna Maria
Prime Location! Waterfront! Walk to it all! Beach!
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 6 beds, 4.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Bradenton
The Florida Rooms
4.95 out of 5 average rating, 41 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
Home in Anna Maria
Heart of Pine Ave | 6 En-Suites | Heated Pool
New place to stay, 6 bedrooms, 8 beds, 6.5 bathrooms
15–20 Aug
Top guest favourite
Home in Bradenton Beach
Gulf Front! Sunset Deck! + Walk to Bridge St Pier!
4.98 out of 5 average rating, 118 reviews, 3 bedrooms, 5 beds, 1 bathroom
13–18 Aug
Home in Bradenton
Private Resort-Style Retreat Near IMG and AMI!
New place to stay, 6 bedrooms, 9 beds, 4 bathrooms
10–15 Aug
Superhost
Home in Sarasota
NEW! Lido Palms Walk to Beach, Pool & Spa, Rooftop
5 bedrooms, 6 beds, 5.5 bathrooms
21–28 Aug
Home in Longboat Key
An Oasis at Little Gull Cottages
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 2 beds, 1 bathroom
7–14 Nov
Top guest favourite
Home in Anna Maria
Bridge and Bay Escape - Brand New Listing!
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 5 beds, 5 bathrooms
31 Jul – 5 Aug
Top guest favourite
Home in Anna Maria
Steps to Beach | Anna Maria Island | Island Time
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 6 beds, 2 bathrooms
20–25 Jul