There's lots to do in Siesta Key, Florida, beyond the beaches, which are some of the best in the state. Read on for our top picks for outdoor activities, shopping, and dining.

The 5-bed, 6-bath Siesta Key estate on Midnight Pass Road was listed for $31.5 million. In July 2025, the listing was removed ...

In related news, a waterfront mansion nearby in Sarasota County hit the real estate market for nearly $30 million earlier ...

Joe and Carla Italiano flew down to Siesta Key from their permanent home in Ontario, Canada, after Hurricane Milton, fearing the worst − but hoping for better − for the famous beach destination that ...

Siesta Key Beautification Alliance spokesperson wants Siesta Key to look like a resort-style area by updating sidewalks, ...

We’re not in the business of predictions, but we'd wager that a recent $9.25 million cash sale for a Siesta Key home will probably end up on our year-end list of the most expensive deals of 2024. What ...

A Herald-Tribune investigation into close contacts between Sarasota County officials and prominent local developers stemmed from the County Commission's handling of citizens' legal challenges to the ...

A holiday pub crawl might be the perfect escape for anyone tired of sitting at home with relatives you barely know — and ...

The Siesta Key cast shared nostalgic posts hinting at the end of the show for good. Pic credit: @madissonhaus/Instagram The Siesta Key: Miami Moves season finale just ended, and fans cannot stop ...

There were plenty of ups and downs in the past 12 months, and the Sarasota/Siesta Key Observer was there to capture it all.

There was something about MTV’s Siesta Key that intrigued me from the very first season. Perhaps it was because I felt personally invalidated by the show. Here were young, wealthy, beautiful ...