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Search results; Over 1,000 homes in Longboat Key

Top guest favourite
Apartment in Longboat Key
Island Time!
Studio, 2 beds, 1 private bathroom
16–21 Aug
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4.98 out of 5 average rating, 245 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
Home in Longboat Key
Waterfront Oasis: Private Heated Pool + Fire Pit
2 bedrooms, 2 beds, 2 bathrooms
15–20 Apr
Apartment in Longboat Key
Harbor Villa Club 206 : Where Fun Meets Relaxation
2 bedrooms, 3 beds, 2 bathrooms
9–16 Jan
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
Superhost
Apartment in Longboat Key
2 Salty by Duncan Real Estate
New place to stay, 1 bedroom, 1 bed, 1 bathroom
8–13 Aug
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
Top guest favourite
Home in Bradenton Beach
Dream State ~ Gulf Front/Across from Beach!
5.0 out of 5 average rating, 20 reviews, 6 bedrooms, 7 beds, 5.5 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Sarasota
Luxe Oasis In St. Armands Circle with Private Pool
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 4 beds, 3 bathrooms
31 Jul – 5 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
Guest favourite
Home in Holmes Beach
Pineapple Paradise | Private Pool | Walk to Beach
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 6 beds, 2 bathrooms
16–23 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
Superhost
Home in Sarasota
New. Luxury Home. Near Siesta Key. Heated Pool.
New place to stay, 4 bedrooms, 5 beds, 2 bathrooms
21–26 Jul
Top guest favourite
Home in Bradenton Beach
Gulf Front! Sunset Deck! + Walk to Bridge St Pier!
4.98 out of 5 average rating, 119 reviews, 3 bedrooms, 5 beds, 1 bathroom
13–18 Aug
Flat in Siesta Key
Villa with private beach, 3 pools complex on beach
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
16–21 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
Guest favourite
Home in Holmes Beach
Black Pearl! NEW! Block and half to Beach!
4.91 out of 5 average rating, 11 reviews, 4 bedrooms, 5 beds, 4 bathrooms
29 Aug – 5 Sept
Superhost
Home in Indian Rocks Beach
Bahia Beachin' Intracoastal Pool Home
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
16–21 Jul