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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
16–21 Aug
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4.87 out of 5 average rating, 206 reviews
Superhost
Casa particular in Longboat Key
Seaside Cottage Retreat Steps Away From the Beach
New place to stay, 2 bedrooms, 4 beds, 2 bathrooms
29 Jul – 5 Aug
Superhost
Flat in Longboat Key
Sea Grape Inn#8- Beachfront Property
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Aug
Superhost
Apartment in Longboat Key
2 Salty by Duncan Real Estate
New place to stay, 1 bedroom, 1 bed, 1 bathroom
10–15 Jul
Top guest favourite
Home in Bradenton
The Florida Rooms
4.95 out of 5 average rating, 39 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
Top guest favourite
Home in Sarasota
Sarasota Bay Retreat - HTD Pool, Dock, 4 Bedroom
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 5 beds, 2 bathrooms
24–31 Jul
Place to stay in Longboat Key
2BR Beachfront Escape – Silver Sands #259 by RVA
2 bedrooms, 4 beds, 2 bathrooms
11–16 Jul
Top guest favourite
Home in Longboat Key
Canal-Front Charmer with Private Beach Access!
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 6 beds, 2 bathrooms
9–14 Jul
Superhost
Flat in Bradenton
The Oasis at One Particular Harbor!
New place to stay, 3 bedrooms, 4 beds, 3 bathrooms
6–11 Jul
Top guest favourite
Apartment in Siesta Key
100 Yds to Beach+2 Blocks to Village | Heated Pool
5.0 out of 5 average rating, 8 reviews, 1 bedroom, 2 beds, 1 bathroom
22–27 Aug
Home in Longboat Key
Artists Retreat, walk to the beach
2 bedrooms, 2 beds, 1 bathroom
4–11 Aug
Top guest favourite
Home in Anna Maria
Bean Pt. Bungalow - Half duplex w/private pool
5.0 out of 5 average rating, 98 reviews, 3 bedrooms, 6 beds, 2 bathrooms
7–12 Sept
Top guest favourite
Home in Holmes Beach
NEW! w/ Pool - The Pearl Unit 2 on AMI
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
7–14 Aug
Top guest favourite
Apartment in Bradenton Beach
Prime Location! Beachfront Condo at Bridgeport
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 7 beds, 2 bathrooms
20–25 Aug
Guest favourite
Home in Sarasota
Luxe Oasis In St. Armands Circle with Private Pool
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 4 beds, 3 bathrooms
7–12 Jul
Top guest favourite
Flat in Longboat Key
Waterfront 2BR 2BA | Pool - 10 min walk to Beach
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–8 Sept
Top guest favourite
Home in Holmes Beach
Rate Sale8/15 Pool~StepsToBeach BeachEquip~Grill
5.0 out of 5 average rating, 62 reviews, 3 bedrooms, 4 beds, 3 bathrooms
15–22 Aug
Top guest favourite
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Jul
Apartment in Siesta Key
Newly Remodeled 2026-Just walk out on to the sand!
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug