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Search results; Over 1,000 homes in Longboat Key

Top guest favourite
Home in Longboat Key
Beautiful Beach House
3 bedrooms, 4 beds, 2 private bathrooms
24–29 Aug
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4.97 out of 5 average rating, 112 reviews
Flat in Longboat Key
Beachfront Bliss | Walk to the Water- 104
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
New place to stay
Home in Longboat Key
Artists Retreat, walk to the beach
2 bedrooms, 2 beds, 1 bathroom
22–29 Aug
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
16–23 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Flat in Longboat Key
Sea Grape Inn#8- Beachfront Property
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Aug
Superhost
Home in Longboat Key
Waterfront Oasis: Private Heated Pool + Fire Pit
2 bedrooms, 2 king beds, 2 bathrooms
15–20 Apr
Luxe
Home in Anna Maria
Bridge and Bay Escape - Brand New Listing!
4 bedrooms, 5 beds, 5 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 9 reviews
Flat in Longboat Key
Fantastic Beach Condo
3 bedrooms, 4 beds, 2 bathrooms
14–19 Jul
Home in Holmes Beach
2-Min Walk to Beach• Heated Pool & Spa • No Stairs
4 bedrooms, 5 beds, 3 bathrooms
28 Aug – 4 Sept
New place to stay
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
Top guest favourite
Home in Bradenton Beach
Gorgeous 4BR w/Htd Pool | Walk 2 Beach | Boat Dock
4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 42 reviews
Guest favourite
Home in Longboat Key
Private Island Beachfront Home
4 bedrooms, 10 beds, 4 bathrooms
16–23 Aug
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Home in Bradenton Beach
New! Pool + Rooftop+ 2 Min Walk to Beach & Bay!
3 bedrooms, 5 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Holmes Beach
TieDyeSky: Waterfall Pool, Steps 2 Beach, Elevator
4 bedrooms, 7 beds, 3 bathrooms
12–19 Sept
5.0 out of 5 average rating, 6 reviews
Home in Tampa
Resort Backyard - Pool, Pickleball & Putting Green
4 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
New place to stay
Superhost
Home in Sarasota
Lido Palms Walk to Beach, Pool & Spa, Rooftop
5 bedrooms, 6 beds, 5.5 bathrooms
21–28 Aug
Flat in Holmes Beach
2BR Family Condo • Heated Pool • Steps to Beach
2 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
New place to stay
Top guest favourite
Home in Holmes Beach
Wonderful 3/2 close to beach! Heated pool!
3 bedrooms, 5 beds, 2 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Anna Maria
Casa Cay by Duncan Real Estate
3 bedrooms, 3 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 18 reviews