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Search results; Over 1,000 homes in Siesta Key

Guest favorite
Villa in Siesta Key
Paradise Villa on Siesta Key
2 bedrooms, 5 beds, 2 private baths
Apr 26 – May 1
,
4.82 out of 5 average rating, 84 reviews
Superhost
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 3 beds, 2 baths
Aug 18 – 23
New place to stay
Top guest favorite
Home in Sarasota
Modern Home Heated Pool near Siesta & Downtown
3 bedrooms, 6 beds, 2 baths
Sep 28 – Oct 3
4.96 out of 5 average rating, 45 reviews
Top guest favorite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds, 5 baths
Sep 24 – 29
5.0 out of 5 average rating, 10 reviews
Home in Sarasota
Heated Pool Retreat | Siesta Key & Downtown
3 bedrooms, 5 beds, 2 baths
Sep 8 – 13
New place to stay
Top guest favorite
Home in Sarasota
Private Oasis: Mini Golf and firepit. 2 king beds.
3 bedrooms, 4 beds, 2 baths
Aug 22 – 27
5.0 out of 5 average rating, 46 reviews
Apartment in Siesta Key
Villa with private beach, 3 pools complex on beach
2 bedrooms, 3 beds, 1 bath
Aug 16 – 21
New place to stay
Guest favorite
Home in Sarasota
Private Heated Pool~Yacht Rental~BBQ~Near Water
3 bedrooms, 5 beds, 2 baths
Aug 22 – 27
5.0 out of 5 average rating, 31 reviews
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Cottage in Sarasota
Cozy Lido Key Studio Steps to Beach & Kayaking
1 bedroom, 1 king bed, 1 bath
Nov 6 – 11
4.98 out of 5 average rating, 59 reviews
Top guest favorite
Home in Siesta Key
Siesta Key Retreat 1mi to Beach!
3 bedrooms, 4 beds, 2 baths
Aug 23 – 30
4.96 out of 5 average rating, 45 reviews
Top guest favorite
Home in Sarasota
Quiet Family Home w/ Pool Near Pinecraft
3 bedrooms, 4 beds, 2 baths
Sep 20 – 25
4.83 out of 5 average rating, 40 reviews
Home in Sarasota
Private Beach•3 Heated Pools•2BR•Ground Floor
2 bedrooms, 3 beds, 2 baths
Aug 29 – Sep 3
New place to stay
Top guest favorite
Home in Sarasota
4BRHeated Pool•Fire Pit•Pool Table Mins Siesta Key
4 bedrooms, 7 beds, 2 baths
Sep 7 – 12
5.0 out of 5 average rating, 23 reviews
Top guest favorite
Home in Sarasota
Luxury Pool Family Paradise-Siesta Key Beach/DT
3 bedrooms, 4 beds, 2 baths
Aug 31 – Sep 5
4.96 out of 5 average rating, 145 reviews
Guest favorite
Home in Sarasota
Coastal Calm
3 bedrooms, 4 beds, 2 baths
Aug 22 – 29
5.0 out of 5 average rating, 6 reviews
Top guest favorite
Cottage in Bradenton Beach
Bradenton Beach Sunsets 2, Anna Maria Island, FL
1 bedroom, 2 beds, 1 bath
Aug 16 – 21
4.98 out of 5 average rating, 254 reviews
Top guest favorite
Home in Sarasota
The Sand Castle - Backyard Oasis Mins from Siesta!
3 bedrooms, 5 beds, 2 baths
Sep 27 – Oct 2
4.94 out of 5 average rating, 167 reviews
Top guest favorite
Condo in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
1 bedroom, 2 beds, 1 bath
Aug 24 – 29
4.96 out of 5 average rating, 67 reviews
Top guest favorite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds, 1 bath
Aug 28 – Sep 2
5.0 out of 5 average rating, 9 reviews