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Search results; Over 1,000 homes in Longboat Key

Top guest favourite
Flat in Longboat Key
Longboat Key-OCEAN FRONT- on the beach
2 bedrooms, 3 beds, 2 private bathrooms
26 Sept – 1 Oct
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4.96 out of 5 average rating, 124 reviews
Flat in Longboat Key
Beachfront Bliss | Walk to the Water- 104
1 bedroom, 2 beds
23–28 Aug
New place to stay
Home in Longboat Key
Artists Retreat, walk to the beach
2 bedrooms, 2 beds
22–29 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Casa particular in Longboat Key
Seaside Cottage Retreat Steps Away From the Beach
2 bedrooms, 4 beds
16–23 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Flat in Longboat Key
Sea Grape Inn#8- Beachfront Property
3 bedrooms, 4 beds
17–22 Aug
Superhost
Home in Longboat Key
Waterfront Oasis: Private Heated Pool + Fire Pit
2 bedrooms, 2 king beds
15–20 Apr
Flat in Longboat Key
Fantastic Beach Condo
3 bedrooms, 4 beds
14–19 Jul
Top guest favourite
Flat in Longboat Key
Waterfront 2BR 2BA | Pool - 10 min walk to Beach
2 bedrooms, 3 beds
15–22 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Apartment in Holmes Beach
#terraceLIFE | 2 Blocks to Beach | Heated Pool
2 bedrooms, 4 beds
9–16 Sept
4.88 out of 5 average rating, 110 reviews
Top guest favourite
Home in Bradenton Beach
Gorgeous 4BR w/Htd Pool | Walk 2 Beach | Boat Dock
4 bedrooms, 6 beds
23–28 Aug
5.0 out of 5 average rating, 42 reviews
Superhost
Home in Sarasota
Lido Palms Walk to Beach, Pool & Spa, Rooftop
5 bedrooms, 6 beds
21–28 Aug
Home in Tampa
Resort Backyard - Pool, Pickleball & Putting Green
4 bedrooms, 5 beds
24–29 Aug
New place to stay
Flat in Holmes Beach
2BR Family Condo • Heated Pool • Steps to Beach
2 bedrooms, 4 beds
7–12 Sept
New place to stay
Top guest favourite
Apartment in Bradenton Beach
Bayfront • Rehabbed • Pickleball • Private Beach
2 bedrooms, 3 beds
25 Aug – 1 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Sarasota
Luxe Oasis In St. Armands Circle with Private Pool
4 bedrooms, 4 beds
17–24 Aug
5.0 out of 5 average rating, 10 reviews
Superhost
Apartment in Longboat Key
2 Salty by Duncan Real Estate
1 bedroom, 1 king bed
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Apartment in Longboat Key
Secluded Bayside Gem with beautiful bay views
2 bedrooms, 3 beds
22–29 Aug
4.97 out of 5 average rating, 72 reviews
Guest favourite
Home in Longboat Key
Private Island Beachfront Home
4 bedrooms, 10 beds
16–23 Aug
4.96 out of 5 average rating, 25 reviews
Guest favourite
Apartment in Holmes Beach
Direct Beach Access & Pool | 2B Full Oceanview
2 bedrooms, 3 beds
29 Aug – 5 Sept
5.0 out of 5 average rating, 5 reviews