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Search results; Over 1,000 homes in Longboat Key

Guest favourite
Home in Longboat Key
Summer House longboat key
3 bedrooms, 6 beds, 3 private bathrooms
5–10 Sept
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4.86 out of 5 average rating, 143 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
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
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
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
Superhost
Home in Sarasota
Waterfront Escape, Heated Pool, Near Lido Beach
3 bedrooms, 6 beds, 3.5 bathrooms
16–21 Sept
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
22–29 Sept
New place to stay
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
Home in Sarasota
Luxe Oasis In St. Armands Circle with Private Pool
4 bedrooms, 4 beds, 3 bathrooms
6–13 Sept
5.0 out of 5 average rating, 10 reviews
Luxe
Home in Sarasota
Lido Palms Walk to Beach, Pool & Spa, Rooftop
5 bedrooms, 6 beds, 5.5 bathrooms
6–13 Sept
Superhost
Home in Longboat Key
Waterfront Oasis: Private Heated Pool + Fire Pit
2 bedrooms, 2 king beds, 2 bathrooms
15–20 Apr
Guest favourite
Home in Holmes Beach
Black Pearl! NEW! Block and half to Beach!
4 bedrooms, 5 beds, 4 bathrooms
5–12 Sept
4.92 out of 5 average rating, 13 reviews
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
Home in Holmes Beach
Beach access + 2 min walk to Sand + Heated Pool!
4 bedrooms, 6 beds, 3 bathrooms
5–12 Sept
5.0 out of 5 average rating, 22 reviews
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
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 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