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Search results; Over 1,000 homes in Longboat Key

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, 239 reviews
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, 6 reviews
Superhost
Apartment in Longboat Key
Sea Grape Inn #6- Beachfront Property
2 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
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
Superhost
Casa particular in Longboat Key
Seaside Cottage Retreat Steps Away From the Beach
2 bedrooms, 4 beds, 2 bathrooms
14–21 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
Guest favourite
Home in Holmes Beach
Pineapple Paradise | Private Pool | Walk to Beach
2 bedrooms, 6 beds, 2 bathrooms
19–26 Sept
5.0 out of 5 average rating, 15 reviews
Superhost
Flat in Longboat Key
Sea Grape Inn#8- Beachfront Property
3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Oct
Rooms in Longboat Key
Gulfside Getaway – Silver Sands Resort #235 by R
2 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Bradenton
The Florida Rooms
3 bedrooms, 3 beds, 2 bathrooms
29 Nov – 4 Dec
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Home in Bradenton Beach
New! Pool + Rooftop+ 2 Min Walk to Beach & Bay!
3 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 13 reviews
Superhost
Home in Sarasota
The Aviator | 7 Mins From SRQ | Pool | Giga Wifi
3 bedrooms, 3 queen beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 3 reviews
Luxe
Home in Sarasota
Lido Palms Walk to Beach, Pool & Spa, Rooftop
5 bedrooms, 6 beds, 5.5 bathrooms
14–21 Sept
Guest favourite
Apartment in Longboat Key
2 Salty by Duncan Real Estate
1 bedroom, 1 king bed, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Holmes Beach
Seaquel A Tropical Retreat - Private Pool Home
3 bedrooms, 3 beds, 2 bathrooms
29 Sept – 6 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Cortez
Heated saltwater CAGED pool ! NEW ! CLEAN !
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.98 out of 5 average rating, 60 reviews
Home in Cortez
Luxury Pet Friendly Waterfront Home in Resort Comm
3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Home in Anna Maria
Bean Pt. Bungalow - Half duplex w/private pool
3 bedrooms, 6 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 109 reviews
Superhost
Home in Longboat Key
Waterfront Oasis: Private Heated Pool + Fire Pit
2 bedrooms, 2 king beds, 2 bathrooms
15–20 Apr