Siesta Key

Siesta Key, frequently rated the #1 beach in the United States, has long been a destination for retirees and visitors. The island is about 8 miles long, and the western shore is covered in beautiful quartz sand.

But it is so much more than that.

While it might seem incongruous at first, those who choose to live there are fortunate to have route choices to get on and off the island, and to their homes, away from the main drag of Siesta Key where you are most likely to find the tourists and visitors having a really good time. With a relatively long history (and our only unsolved murder, that of Harry Higel, local resident and developer, back in 1921). 

On Sunday evenings as the sun prepares to go down, an informal group has been forming for something like 40 years near the lifeguard shacks, and thus begins the Drum Circle. It grew from just a few locals having a good time, to a group of many many performers (drums, didgeridoos, etc) and dancers every Sunday. (you can see it towards the end of the posted video)

As I write this, the lowest priced property on the island is listed for sale at $325,000, a studio condo in a complex that has direct beach access and you can do weekly rentals there. The lowest priced single family home listed today (July 2026) is $750,000 for a storm damaged home. NOTE: in Florida, there is something called in short hand as the "50% rule," and generally speaking, if you buy a property in a flood zone (ALL the islands and bay front / near bay front properties are going to be in flood zones) and you want to improve the property, if the value of the improvement will exceed 50% of the value of the "improvements" (home) on the property, then the entire improvement must be brought up to current code. 

So, in the example of the single family home mentioned above, the tax assessor's office values the "improvements" at $90,000 (with a land value of $626,000) so if you wanted to improve the existing structure and those improvements would cost $45,000 or more, you would encounter the 50% rule and be required to bring the entire structure up to code. (I'd recommend you consider discussing this with a real estate attorney if you are looking to buy a property on one of the islands, particularly one you might be inclined to renovate)