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Search results; Over 1,000 homes in Longboat Key

Top guest favourite
Apartment in Longboat Key
The Beach Condo #107 Beachfront Full View
Studio, 2 beds, 1 private bathroom
4–9 Oct
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4.87 out of 5 average rating, 209 reviews
Guest favourite
Flat in Longboat Key
Beachfront Bliss | Walk to the Water- 104
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Holmes Beach
Pineapple Paradise | Private Pool | Walk to Beach
2 bedrooms, 6 beds, 2 bathrooms
5–12 Sept
5.0 out of 5 average rating, 15 reviews
Home in Longboat Key
Artists Retreat, walk to the beach
2 bedrooms, 2 beds, 1 bathroom
4–11 Sept
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
4–11 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Sarasota
Waterfront Escape, Heated Pool, Near Lido Beach
3 bedrooms, 6 beds, 3.5 bathrooms
16–21 Sept
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, 48 reviews
Guest favourite
Apartment in Longboat Key
2 Salty by Duncan Real Estate
1 bedroom, 1 king bed, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 5 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
Apartment in Sarasota
Sarasota Designer Waterfront Retreat * Paddleboard
2 bedrooms, 2 beds, 1.5 bathrooms
5–12 Sept
New place to stay
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
Luxe
Home in Sarasota
Lido Palms Walk to Beach, Pool & Spa, Rooftop
5 bedrooms, 6 beds, 5.5 bathrooms
6–13 Sept
Home in Holmes Beach
Lakefront · Fishing ·Heated Pool ·Walk to Beach
3 bedrooms, 3 beds, 3 bathrooms
19–26 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, 108 reviews
Guest favourite
Apartment in Bradenton Beach
Charming Coastal Stay on Anna Maria Island
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 11 reviews
Superhost
Home in Longboat Key
Waterfront Oasis: Private Heated Pool + Fire Pit
2 bedrooms, 2 king beds, 2 bathrooms
15–20 Apr
Top guest favourite
Apartment in Holmes Beach
#terraceLIFE | 2 Blocks to Beach | Heated Pool
2 bedrooms, 4 beds, 2 bathrooms
9–16 Sept
4.88 out of 5 average rating, 112 reviews
Top guest favourite
Apartment in Siesta Key
❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 172 reviews
Top guest favourite
Home in Bradenton Beach
New! Pool + Rooftop+ 2 Min Walk to Beach & Bay!
3 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 13 reviews