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Search results; Over 1,000 homes in Longboat Key

Guest favourite
Townhouse in Longboat Key
Updated Townhome, Secluded Beach + Pool
2 bedrooms, 4 beds, 2.5 shared bathrooms
14–21 Sept
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5.0 out of 5 average rating, 41 reviews
Guest favourite
Flat in Longboat Key
Beachfront Bliss | Walk to the Water- 104
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
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
14–21 Sept
5.0 out of 5 average rating, 3 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
Top guest favourite
Apartment in Longboat Key
Secluded Bayside Gem with beautiful bay views
2 bedrooms, 3 beds, 2 bathrooms
3–10 Oct
4.97 out of 5 average rating, 72 reviews
Home in Longboat Key
Bayou and Beach Longboat Key Private Home
5 bedrooms, 6 beds, 4 bathrooms
21–26 Mar
5.0 out of 5 average rating, 4 reviews
Guest favourite
Apartment in Longboat Key
2 Salty by Duncan Real Estate
1 bedroom, 1 king bed, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 5 reviews
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 Longboat Key
Private Island Beachfront Home
4 bedrooms, 10 beds, 4 bathrooms
14–21 Sept
4.96 out of 5 average rating, 26 reviews
Home in Longboat Key
An Oasis at Little Gull Cottages
1 bedroom, 2 beds, 1 bathroom
6–11 Mar
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Holmes Beach
Best Deal Ever starts 9/16~Pool, Steps to beach!
3 bedrooms, 4 beds, 3 bathrooms
16–23 Sept
5.0 out of 5 average rating, 65 reviews
Superhost
Apartment in Longboat Key
Sea Grape Inn #6- Beachfront Property
2 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
Top guest favourite
Apartment in Bradenton Beach
Largest Pool • Private Beach Access • Pickleball
2 bedrooms, 3 beds, 2 bathrooms
14–21 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Holmes Beach
NEW! w/ Pool - The Pearl Unit 2 on AMI
2 bedrooms, 2 beds, 1.5 bathrooms
14–21 Sept
5.0 out of 5 average rating, 11 reviews
Room in Longboat Key
Oceanfront Oasis – Longboat Key 226 by RVA
2 beds, 1 bathroom
20–25 Sept
4.67 out of 5 average rating, 6 reviews
Top guest favourite
Home in Bradenton Beach
Gulf Front! Sunset Deck! + Walk to Bridge St Pier!
3 bedrooms, 5 beds, 1 bathroom
14–19 Sept
4.98 out of 5 average rating, 128 reviews
Apartment in Sarasota
Sarasota Designer Waterfront Retreat * Paddleboard
2 bedrooms, 2 beds, 1.5 bathrooms
22–29 Sept
New place to stay
Flat in Longboat Key
Fantastic Beach Condo
3 bedrooms, 4 beds, 2 bathrooms
14–19 Jul
Guest favourite
Home in Bradenton
Cottage on the canal
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 20 reviews