Some residents, like Jean Cannon, feel the frustration of Siesta Key’s growing problem with transient visitors
After 24 years of living in the gulf-front townhouse of her dreams, Jean Cannon is putting it up for sale.
She’ll leave behind her lush, impeccable front-yard garden — the one she’s doted upon on a daily basis.
The endless deep-blue views and easy-access beach walks? They’ll be gone.
She’s doing this not because she wants to downsize, needs the money, or is trying to strike during a strong seller’s market.
No, it’s because she’s simply fed up with the chaos across the street.
“It has become way too much. I have been pushed out,” said the resident of the 500 block of Beach Road, between beach accesses 9 and 10. “I’m tired of calling the cops because of the noise, knowing there’s nothing they will do. That’s silly. I don’t want to be the grumpy old lady on the block.”
The rental of single-family homes for less than 30 days is illegal here, but it’s become a widespread reality on the Key and certainly in Cannon’s highly sought-after neighborhood. When two new, four-story buildings were built across the street from Cannon in 2014, complete with three large street-side balconies, the growing problem was suddenly right on top of her.
“There were some old Florida homes there and, when they began to tear them down, I thought ‘Great. They’re really upgrading the neighborhood.’ Well, that’s not what happened at all,” she said. “This is what I got instead.”
The first sign of trouble was when she saw advertisements out front stating that each house could accommodate 24 people.

Today, both structures are for sale with a sign noting “income producing” on them.
Meanwhile, a group shows up for the weekends, followed by another during the weekdays.
That cycle has been on nothing other than repeat.
“This spring season was especially bad,” Cannon said. “They would party and shout back and forth on the balconies, all six of them. And the voices and music carry like you can’t believe.
“Then there are the cars. They are everywhere, including the lawn. But the police won’t do anything if they aren’t blocking the sidewalk.
“It would be one thing if there was someone I could call. Like at a hotel, you call the front desk. But in this case, I have no idea who owns them.”
Cannon used to own a rental property in the Florida Keys, where owners had to register with the municipality, pass an annual fire inspection, and have their contact information mounted on a plaque outside the front door.
Sarasota County does not require such measures, but leaders are beginning to explore their options (see story below).
“Let’s face it, the county wasn’t prepared for this,” Cannon said. “Many of these (rentals) are not run legally, and we all know it.
“You’ve got hotels that aren’t really hotels. It’s all far too dense.”
That type of influx of people is hard on more than just the residents, she said.
“It’s also an assault on our environment,” said Cannon, who hopes to rent in the area so she can continue to work on the canal regeneration project on the Key. “If we don’t run things effectively here, we’ll lose this beauty we have.”
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It’s one thing to see illegal short-term rentals on the main drag in the heart of the island’s tourist area, where Cannon lives. But off the beaten path near Boyd Park?
Indeed, the Village and beaches are far from the Waterside East neighborhood where Victoria Popowick lives on the north part of the Key.
“This is as residential as it gets,” she said.
That’s why she was worried when “an army of workers” arrived in October to overhaul a large home near her Commonwealth Drive residence.
“The owners went to the neighbors and introduced themselves. They even gave us gifts. And that’s the last we’ve seen of them,” Popowick said. “Since then, the house has more than 20 people in it at a time. And they overload the waste receptacle the county gives everyone.
“Because of all the trash that sits out for days, we now have a big problem. My husband reached for a trash can that had a loose lid and a rat ran up his arm.”
Meanwhile, the noise at the backyard pool is so loud “it feels like it’s in my living room,” Popowick said. “They ruined my Christmas.”
When she contacted the out-of-state owners, they said they’d have their lawyer look into the situation.
“That was a big ‘F-you’ as far as I’m concerned,” Popowick said. “I’ve called the sheriff numerous times, but nothing happens. Sometimes I feel bad, because I know these people are on vacation and they’ve spent a lot of money. That house brings in as much as $1,600 a night.
“It’s the owners who are to blame. The county, too. There’s no regulation.”
Popowick also said her neighborhood is seeing a spike in break-ins.
“My neighbor just listed his house for sale last week. He’s had enough.”
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Just around the corner on Venice Lane, Jim Dragatsis is dealing with a similar scene with another large rental that sits next door.
“My twin 11-year-old girls couldn’t be in my own backyard during Easter because of all the swearing coming from the guests next door,” he said. “I mean, I live here. This is my home. I’m talking about selling. I’m not going to live next to this.”
Between 12 and 15 people occupy the home usually a week at a time, he said, but the parties bring dozens more. It’s owned by someone in Ohio, Dragatsis continued, and whenever the authorities are called the guests have been coached to respond that they are “friends of the owner” so they can avoid trespassing accusations.
Even Dragatsis’ canal is suffering from overload.
“A 27-foot boat pulled up with a bunch of people. That’s way too big,” he said. “And once, someone’s pontoon was tied up to my dock.”
The house was built in 2018 after the previous structire was torn down. Dragatsis said his research has shown that the owner is planning to sell the property to his son in order to get a clean record and void the list of complaints.
“It’s a trick they use, and it’s all just so blatant,” Dragatsis said. “It’s the Wild West. They do whatever they want. What they’re actually doing is disturbing people’s neighborhoods. I know I’m not alone.”
In fact, further research revealed a daunting situation, he said.
“I’ve been told there are 350 illegal rentals on Siesta Key,” Dragatsis said. “This is a tough position for us to be in.”
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Recently, longtime resident Joe Volpe watched a house down his street on the corner of Treasure Boat Way and Sandy Hook Road North go through an interesting transformation.
“They split it in half, and that’s as illegal as hell,” he said of the property just north of the Village. “They put walls inside and certainly didn’t pull any permits — had they applied for them, they wouldn’t have been allowed to do what they did.
“It now has two addresses. Even two mailboxes.”
It also has all the trouble synonymous with illegal short-term rentals, he said.
“After people leave at the end of the weekend, the trash sits out in this heat from Monday until it’s picked up on Wednesday,” Volpe. “And there are always parties. Thirty cars were here on the Fourth of July.”
Volpe said he’s even gotten into physical confrontations with guests when he approached them with his concerns.
Beyond the behavior, he’s worried about a lack of safety.
“They are essentially hotels, but they don’t meet any of the requirements,” Volpe said. “No fire escapes, lit exits, fire extinguishers, and those doors are not fire doors.
“We’re talking about a bunch of strangers living together. I doubt most of them could even give the address if they had to call 911 in case of a fire.”
A native of Michigan, Volpe has been keeping an eye on how his home state is handling the problem. He thinks its leaders found the right solution and hopes Sarasota County will do the same.
“They determined that they are hotels, or motels. And as such, they have to meet the requirements. And none of them can,” he said. “That’s how you get rid of them.
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As for Graham Clark, he’s taking a rather unorthodox approach to his fight against what are often loud and disrespectful short-term renters next door. The parties, he said, are often as large as 30 people.
“Asking them nicely to turn down the music doesn’t work,” said Clark, who moved to a house on Oxford Drive two years ago. “Believe me, I’ve tried.
So now, he fights fire with fire.
“They’ll have a radio blaring on the dock after midnight. So, I point my bass amp at them and blast the most offensive, the most vulgar, the raunchiest rap music I can find. Eventually, they’ll go back inside. It actually works.”
He’s also a resident of what is considered canal country, back near Palm Island, and he said the noise freely carries across the waterways for blocks.
Do his neighbors mind his method of battle?
“Actually, I’ll hear them shout ‘Go Graham, go!’ down the canal. They all know something has got to be done,” Clark said. “See? I’ve got back-up.”
He’s also had strangers’ boats docked on his property — “The boatlift at the rental is broken,” he said — and one day visitors went to Disney World for the day and left a non-stop barking dog out on the balcony.
“The lack of consideration is mind-blowing,” Clark said. “So, what I’m going to do is ruin their vacation.”
He chose the neighborhood because it appeared quiet. One house was for rent at the time, he said, but he never imagined it would become something of constant turnover.
“There’s a lady on the other side in her 80s,” Clark said. “I feel terrible for her.”
He actually doesn’t blame the owners as much as the rental companies that represent them. He often reads about complaints against them and their properties on the SeeClick.Fix.com app — a community bulletin board said describes itself as “bridging the communication gap between residents and their local governments.”
“Go to a location and you’ll see the code-enforcement listings (involving a property),” he said.
While Siesta Key residents deal with the potential arrival of as many as four new hotels, Clark said he thinks illegal short-term rentals should be the biggest concern.
“We should be asking the hotel people to put up some money to help create laws against these short-term rentals. They should be happy to do it, because these renters will instead go to their hotels. In return, the residents will stop showing up at meetings and slowing the process,” Clark said. “They are going to get their hotels. I don’t think they can be stopped.
“It is these illegal rentals that must be stopped.”