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Search results; Over 1,000 homes in Longboat Key

Guest favourite
Townhouse in Longboat Key
Updated Townhome, Secluded Beach + Pool
2 bedrooms, 4 beds, 2.5 shared bathrooms
4–11 Jul
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5.0 out of 5 average rating, 38 reviews
Home in Longboat Key
Artists Retreat, walk to the beach
2 bedrooms, 2 beds, 1 bathroom
17–24 Jul
Superhost
Apartment in Longboat Key
2 Salty by Duncan Real Estate
1 bedroom, 1 king bed, 1 bathroom
10–15 Jul
New place to stay
Top guest favourite
Home in Longboat Key
Canal-Front Charmer with Private Beach Access!
4 bedrooms, 6 beds, 2 bathrooms
9–14 Jul
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Longboat Key
North Longboat Modern Beach House Gem
4 bedrooms, 4 beds, 3.5 bathrooms
31 Jul – 7 Aug
Guest favourite
Home in Longboat Key
Private Island Beachfront Home
4 bedrooms, 10 beds, 4 bathrooms
5–12 Jul
4.96 out of 5 average rating, 25 reviews
Superhost
Home in Bradenton
Luxury Estate w/ Amazing Outdoor Space, Slps 24
7 bedrooms, 12 beds, 5 bathrooms
1–6 Jul
New place to stay
Guest favourite
Home in Sarasota
Luxe Oasis In St. Armands Circle with Private Pool
4 bedrooms, 4 beds, 3 bathrooms
7–12 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Anna Maria
Bridge and Bay Escape - Brand New Listing!
4 bedrooms, 5 beds, 5 bathrooms
31 Jul – 5 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Bradenton Beach
Gulf Front! Sunset Deck! + Walk to Bridge St Pier!
3 bedrooms, 5 beds, 1 bathroom
21–26 Jul
4.98 out of 5 average rating, 116 reviews
Home in Holmes Beach
TieDyeSky: Waterfall Pool, Steps 2 Beach, Elevator
4 bedrooms, 7 beds, 3 bathrooms
22–29 Aug
5.0 out of 5 average rating, 3 reviews
Home in Siesta Key
Waterfront Home Pool & Dock 5 Min to Siesta Beach
3 bedrooms, 4 beds, 2 bathrooms
18–23 Jul
Superhost
Home in Anna Maria
Steps to Beach | Anna Maria Island | Island Time
3 bedrooms, 6 beds, 2 bathrooms
20–25 Jul
5.0 out of 5 average rating, 3 reviews
Home in Siesta Key
House on Siesta Key with Private Pool and Hot tub!
4 bedrooms, 4 beds, 4 bathrooms
20–25 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Bradenton Beach
Walk to it all! Restaurants + Heated Pool +Beach!
3 bedrooms, 7 beds, 3 bathrooms
14–19 Aug
5.0 out of 5 average rating, 103 reviews
Superhost
Apartment in Bradenton Beach
Pickleball/Tennis • Beach Access •Newly Rehabbed
2 bedrooms, 3 beds, 2 bathrooms
30 Jul – 6 Aug
New place to stay
Top guest favourite
Home in Holmes Beach
Swell Life-Beach Front Home!
4 bedrooms, 6 beds, 4 bathrooms
15–22 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Sarasota
Pool • Walk to Beach • St Armands Circle•Sleeps 12
4 bedrooms, 6 beds, 3 bathrooms
4–11 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Flat in Longboat Key
Sea Grape Inn#8- Beachfront Property
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Aug