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Search results; Over 1,000 places

Guest favorite
Condo in Siesta Key
Seaside on Siesta Key Beach
3 min walk
May 16 – 23
4.99 out of 5 average rating, 67 reviews
Guest favorite
Condo in Siesta Key
NO Stairs, beachfront & short walk to the village!
10 min walk
Apr 27 – May 2
4.92 out of 5 average rating, 87 reviews
Guest favorite
Apartment in Siesta Key
Renovated beachside condo-direct beach access
2 min drive
May 26 – 31
4.95 out of 5 average rating, 37 reviews
Superhost
Apartment in Siesta Key
Sunset Sensation
6 min walk
May 4 – 9
5.0 out of 5 average rating, 3 reviews
Guest favorite
Condo in Siesta Key
Sarasota Surf & Racquet Club Siesta Key Condo
14 min walk
May 4 – 9
4.83 out of 5 average rating, 122 reviews
Guest favorite
Condo in Siesta Key
Sarasota Surf & Racquet Club Siesta Key Condo
2 min drive
May 18 – 23
4.91 out of 5 average rating, 78 reviews
Guest favorite
Apartment in Siesta Key
Siesta Key #1 Beach, pickle ball & tennis paradise
2 min drive
Aug 2 – 7
4.99 out of 5 average rating, 139 reviews
Guest favorite
Condo in Siesta Key
Walk to Siesta Key Village and Beach
4 min drive
Apr 28 – May 3
4.95 out of 5 average rating, 148 reviews
Superhost
Condo in Siesta Key
LUXECottage @Crystal Sands -Siesta Key Beachfront!
6 min walk
May 18 – 25
4.91 out of 5 average rating, 55 reviews
Guest favorite
Condo in Siesta Key
Amazing beach view! Entire unit renovated!
5 min walk
May 28 – Jun 4
5.0 out of 5 average rating, 17 reviews
Superhost
Condo in Siesta Key
Siesta Key Beach Escape
4 min walk
May 19 – 26
4.89 out of 5 average rating, 116 reviews
Guest favorite
Condo in Siesta Key
❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
5 min drive
Apr 28 – May 3
5.0 out of 5 average rating, 64 reviews
Guest favorite
Condo in Sarasota
Location,Location,Location-Beachfront-Siesta Key
5 min drive
May 6 – 11
4.97 out of 5 average rating, 66 reviews
Guest favorite
Apartment in Siesta Key
Siesta Sunset Condo
2 min drive
May 2 – 9
5.0 out of 5 average rating, 7 reviews
Guest favorite
Apartment in Siesta Key
Across from beach & walk to town
10 min walk
Apr 26 – May 1
5.0 out of 5 average rating, 15 reviews
Guest favorite
Home in Siesta Key
Lovely Siesta Key house near beach w/ heated pool!
10 min walk
May 10 – 15
4.94 out of 5 average rating, 68 reviews
Guest favorite
Home in Siesta Key
Beachfront 180-Degree View, Walk to Village!
3 min drive
Apr 20 – 27
5.0 out of 5 average rating, 22 reviews
Guest favorite
Home in Siesta Key
Beachfront home with private access, walk to town!
2 min drive
May 5 – 10
4.95 out of 5 average rating, 87 reviews