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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Apartment in Siesta Key
Beach & Pool Open! Direct Beachfront Condo! Sunset
2 bedrooms, 3 beds, 2 private bathrooms
29 Aug – 5 Sept
,
4.94 out of 5 average rating, 77 reviews
Superhost
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds, 5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Sarasota
Luxury Lido Key Heated Pool & Game Room
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Siesta Key
House on Siesta Key with Private Pool and Hot tub!
4 bedrooms, 4 beds, 4 bathrooms
19–24 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Siesta Key
Villa Fiesta - 312
2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Jul
New place to stay
Home in Sarasota
The Siesta Key Retreat - An Island Garden Oasis!
4 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
New place to stay
Guest favourite
Home in Sarasota
Dream's Corner Cove
3 bedrooms, 6 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Sarasota
LA Luxury & Heated Pool Oasis 12 min to Siesta Key
4 bedrooms, 2 beds, 3 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds, 1 bathroom
8–15 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Apartment in Sarasota
Direct Gulf View - Residence 505
4 bedrooms, 4.5 bathrooms
26–31 Aug
Top guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
4.93 out of 5 average rating, 58 reviews
Top guest favourite
Home in Sarasota
The Ashton Retreat
2 bedrooms, 2 double beds, 1 bathroom
26–31 Jul
4.96 out of 5 average rating, 51 reviews
Top guest favourite
Home in Sarasota
NEW Luxe Resort Home*XL Pool/Hot Tub*1 mi to Beach
3 bedrooms, 6 beds, 2 bathrooms
9–14 Aug
4.97 out of 5 average rating, 29 reviews
Home in Anna Maria
Heart of Pine Ave | 6 En-Suites | Heated Pool
6 bedrooms, 8 beds, 6.5 bathrooms
15–20 Aug
New place to stay
Guest favourite
Home in Sarasota
Big backyard hangout, firepit, large primary suite
3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Sarasota
The Palms Away
2 bedrooms, 2 beds, 1.5 bathrooms
5–10 Aug
5.0 out of 5 average rating, 33 reviews
Superhost
Home in Bradenton
Sleeps 24 · Heated Pool · Pickleball · Arcade
7 bedrooms, 12 beds, 5 bathrooms
7–12 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Sarasota
Coastal Luxe, SaltPool/heatSpa, 5 miles to Siesta
5 bedrooms, 10 beds, 5 bathrooms
23–30 Aug
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Home in Bradenton
Pool & Sand Volleyball | 3 Kings | Near AMI & IMG
4 bedrooms, 5 beds, 3 bathrooms
9–14 Aug
4.98 out of 5 average rating, 42 reviews