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Search results; Over 1,000 homes in Longboat Key

Guest favourite
Apartment in Longboat Key
Beachfront Resort, Ocean View, Pool, Tennis, Gym
1 bedroom, 2 beds, 1 private bathroom
18–23 Sept
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4.89 out of 5 average rating, 227 reviews
Superhost
Casa particular in Longboat Key
Seaside Cottage Retreat Steps Away From the Beach
2 bedrooms, 4 beds, 2 bathrooms
29 Jul – 5 Aug
New place to stay
Top guest favourite
Home in Bradenton
The Florida Rooms
3 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.95 out of 5 average rating, 40 reviews
Superhost
Apartment in Longboat Key
2 Salty by Duncan Real Estate
1 bedroom, 1 king bed, 1 bathroom
10–15 Jul
New place to stay
Top guest favourite
Home in Holmes Beach
NEW! w/ Pool - The Pearl Unit 1 on AMI
1 bedroom, 2 beds, 1 bathroom
23–30 Aug
5.0 out of 5 average rating, 8 reviews
Superhost
Flat in Longboat Key
Sea Grape Inn#8- Beachfront Property
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Aug
Top guest favourite
Apartment in Bradenton Beach
Prime Location! Beachfront Condo at Bridgeport
2 bedrooms, 7 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Siesta Key
100 Yds to Beach+2 Blocks to Village | Heated Pool
1 bedroom, 2 beds, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Longboat Key
Canal-Front Charmer with Private Beach Access!
4 bedrooms, 6 beds, 2 bathrooms
9–14 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Holmes Beach
NEW! w/ Pool - The Pearl Unit 2 on AMI
2 bedrooms, 2 beds, 1.5 bathrooms
7–14 Aug
5.0 out of 5 average rating, 7 reviews
Superhost
Flat in Bradenton
The Oasis at One Particular Harbor!
3 bedrooms, 4 beds, 3 bathrooms
6–11 Jul
New place to stay
Top guest favourite
Home in Anna Maria
Bean Pt. Bungalow - Half duplex w/private pool
3 bedrooms, 6 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 98 reviews
Top guest favourite
Flat in Longboat Key
Waterfront 2BR 2BA | Pool - 10 min walk to Beach
2 bedrooms, 3 beds, 2 bathrooms
1–8 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Holmes Beach
Rate Sale8/15 Pool~StepsToBeach BeachEquip~Grill
3 bedrooms, 4 beds, 3 bathrooms
15–22 Aug
5.0 out of 5 average rating, 62 reviews
Top guest favourite
Apartment in Holmes Beach
A Coastal Retreat Steps From the Sea
2 bedrooms, 4 beds, 2 bathrooms
30 Jul – 6 Aug
4.98 out of 5 average rating, 105 reviews
Top guest favourite
Townhouse in Holmes Beach
Getaway Family Beach Townhome w/Pool!
2 bedrooms, 5 beds, 2 bathrooms
14–21 Aug
4.94 out of 5 average rating, 66 reviews
Place to stay in Longboat Key
2BR Beachfront Escape – Silver Sands #259 by RVA
2 bedrooms, 4 beds, 2 bathrooms
25–30 Jul
Top guest favourite
Apartment in Siesta Key
❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
1 bedroom, 1 king bed, 1 bathroom
30 Jul – 4 Aug
5.0 out of 5 average rating, 163 reviews
Apartment in Siesta Key
Newly Remodeled 2026-Just walk out on to the sand!
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug