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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
Home in Longboat Key
Artists Retreat, walk to the beach
2 bedrooms, 2 beds, 1 bathroom
27 Aug – 3 Sept
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
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
Flat in Longboat Key
Fantastic Beach Condo
3 bedrooms, 4 beds, 2 bathrooms
14–19 Jul
Superhost
Flat in Longboat Key
Sea Grape Inn#8- Beachfront Property
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
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
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, 43 reviews
Top guest favourite
Home in Anna Maria
Bean Pt. Bungalow - Half duplex w/private pool
3 bedrooms, 6 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 106 reviews
Top guest favourite
Home in Sarasota
Siesta Serenity ~ Pool/Waterslide/Waterfront
4 bedrooms, 5 beds, 4 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 22 reviews
Home in Holmes Beach
3BR Dog Friendly | Pool | Patio | Garage Parking
3 bedrooms, 5 beds, 2 bathrooms
21–28 Aug
New place to stay
Home in Indian Shores
Fragrance-Free Beach Retreat | Pool + Beach Access
3 bedrooms, 6 beds, 2 bathrooms
24–29 Aug
New place to stay
Guest favourite
Home in Holmes Beach
Steps to Beach - Prime Location - Beach Bungalow
3 bedrooms, 5 beds, 2 bathrooms
21–28 Aug
5.0 out of 5 average rating, 5 reviews
Place to stay in Longboat Key
Silver Sands Serenity – Unit 234 by RVA
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
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
21–28 Aug
5.0 out of 5 average rating, 10 reviews
Home in Bradenton
Casita Haven Retreat | Peaceful Coastal Getaway
3 bedrooms, 6 beds, 2 bathrooms
21–26 Aug
5.0 out of 5 average rating, 3 reviews
Home in Bradenton Beach
Island Breeze Escape
2 bedrooms, 3 beds, 2 bathrooms
21–28 Aug
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