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Search results; Over 1,000 homes in Longboat Key

Top guest favorite
Condo in Longboat Key
Panoramic Gulf views from your balcony
1 bedroom, 3 beds, 1 private bath
Sep 23 – 28
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4.89 out of 5 average rating, 122 reviews
Superhost
Casa particular in Longboat Key
Heated pool and wrap-around balcony near beach
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 4 beds, 2 baths
Aug 12 – 19
Home in Longboat Key
Walk to the beach with a kayak
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 12 – 19
Top guest favorite
Apartment in Longboat Key
Bayfront views from a private patio
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 3 beds, 2 baths
Sep 15 – 22
Superhost
Condo in Longboat Key
Beachfront with direct Gulf walkout
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bath
Aug 12 – 17
Top guest favorite
Apartment in Bradenton Beach
Beachfront corner unit with Gulf sunsets
4.98 out of 5 average rating, 53 reviews, 1 bedroom, 2 beds, 1 bath
Oct 10 – 15
Guest favorite
Home in Holmes Beach
Retro flamingo house with a private pool
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 6 beds, 2 baths
Aug 16 – 23
Top guest favorite
Home in Anna Maria
Private saltwater pool near the beach
5.0 out of 5 average rating, 105 reviews, 3 bedrooms, 6 beds, 2 baths
Aug 23 – 28
Superhost
Home in Sarasota
Heated pool, arcade, and fire pit
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 5 beds, 2 baths
Sep 9 – 14
Top guest favorite
Home in Bradenton
Resort pool, spa, and fire pit
4.96 out of 5 average rating, 45 reviews, 3 bedrooms, 3 beds, 2 baths
Oct 26 – 31
Top guest favorite
Home in Bradenton
Heated pool and a stroll to the bay
4.97 out of 5 average rating, 66 reviews, 3 bedrooms, 5 beds, 2 baths
Oct 22 – 27
Top guest favorite
Condo in Bradenton Beach
Heated saltwater pool and private beach
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 25 – Sep 1
Top guest favorite
Home in Bradenton Beach
Heated pool, one block from Bridge Street
4.98 out of 5 average rating, 111 reviews, 3 bedrooms, 7 beds, 3 baths
Aug 14 – 19
Guest favorite
Home in Bradenton Beach
One block from the bay in Cortez
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 16 – 21
Superhost
Home in Longboat Key
Waterfront with a heated pool and dock
2 bedrooms, 2 beds, 2 baths
Apr 15 – 20
Guest favorite
Home in Bradenton
Heated pool, pickleball court, and game room
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 6 beds, 2 baths
Aug 24 – 29
Top guest favorite
Home in Bradenton
Heated pool, mini golf, and arcade
5.0 out of 5 average rating, 86 reviews, 3 bedrooms, 5 beds, 2 baths
Aug 23 – 28
Rooms in Longboat Key
Beachfront resort with a heated pool
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 4 beds, 2 baths
Aug 20 – 25
Guest favorite
Home in Holmes Beach
Beach views from the balcony, with pool
4.91 out of 5 average rating, 11 reviews, 4 bedrooms, 6 beds, 4 baths
Aug 15 – 22