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Search results; Over 1,000 homes in Longboat Key

Top guest favourite
Apartment in Longboat Key
Island Time: Open August 30th - September 3rd!
Studio, 2 beds, 1 private bathroom
9–14 Nov
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4.98 out of 5 average rating, 252 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
Home in Longboat Key
Waterfront Oasis: Private Heated Pool + Fire Pit
2 bedrooms, 2 king beds, 2 bathrooms
15–20 Apr
Superhost
Flat in Longboat Key
Sea Grape Inn#8- Beachfront Property
3 bedrooms, 4 beds, 2.5 bathrooms
18–23 Aug
Flat in Longboat Key
Fantastic Beach Condo
3 bedrooms, 4 beds, 2 bathrooms
14–19 Jul
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
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
Apartment in Longboat Key
Secluded Bayside Gem with beautiful bay views
2 bedrooms, 3 beds, 2 bathrooms
22–29 Aug
4.97 out of 5 average rating, 72 reviews
Guest favourite
Home in Sarasota
Luxe Oasis In St. Armands Circle with Private Pool
4 bedrooms, 4 beds, 3 bathrooms
19–26 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Longboat Key
Private Island Beachfront Home
4 bedrooms, 10 beds, 4 bathrooms
18–25 Aug
4.96 out of 5 average rating, 25 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, 110 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
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
6–13 Sept
Guest favourite
Home in Holmes Beach
Steps to Beach - Prime Location - Beach Bungalow
3 bedrooms, 5 beds, 2 bathrooms
18–25 Aug
5.0 out of 5 average rating, 5 reviews
Home in Longboat Key
Lovely townhouse on Sarasota Bay
2 bedrooms, 3 beds, 2.5 bathrooms
18–23 Aug
Superhost
Home in Clearwater
Beachfront Paradise Pet Friendly home
4 bedrooms, 7 beds, 3 bathrooms
18–23 Aug
Superhost
Apartment in Longboat Key
2 Salty by Duncan Real Estate
1 bedroom, 1 king bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 4 reviews