Fourteen candidates enter for five hotly-contested Islamorada Village Council seats this November. With the most candidates seen in the village’s history, the hopefuls consist of incumbents and newcomers, Conchs and longtime residents and men and women of all backgrounds. Now through Election Day, the Upper Keys Weekly will ask the candidates questions on key issues facing the village.

Answers are printed exactly as submitted by candidates, with responses limited to 75 words.

The Upper Keys Weekly asked the candidates: How would you go about addressing the issue of illegal vacation rentals in the village?


Buddy Pinder

I am confident that the Village Code’s Compliance Officers, the Planning Director and the Village Manager are utilizing all tools available to identify illegal vacation rental activity within the village and to cite them according to the limits of state and local laws. Until the State of Florida supports local government efforts to regulate vacation rentals within their jurisdictions, the village’s efforts are hindered. Through the village’s membership in the Florida League of Cities and through our state lobbyists, I would seek changes in laws that have limited local government home rule authority over vacation rentals in the State of Florida so that full-time residents and property owners enjoy an enhanced quality of life.

Sue Miller

The enforcement effort should be enhanced and communicated broadly so the entire community knows illegal vacation rentals aren’t tolerated. Fines were established by resolution in 2009. Some owners consider the fine the cost of doing business. Fines need to be a true deterrent, perhaps a multiple of advertised weekly rental rate. Some rental rates are as much as $1,000 – $3,000/night! Keep improving monitoring practices. Have community volunteers monitor online advertisements to assist code enforcement.


Mark Gregg

I would continue improving our current enforcement efforts using our newly acquired specialty software that tracks illegal vacation rental advertising and create a special code enforcement unit with enhanced investigation techniques and capabilities to gather better evidence for more successful prosecutions with increased fines equal to the revenue received by the violators from illegal rental activity. I would also support the creation of neighborhood citizen groups to report suspected illegal rentals to a hotline.

Mary Barley

First, we must be serious about this problem, and I have not seen anything from the village that suggests we are. Purchasing software doesn’t solve the problem, actions do. Staff must be instructed to search carefully, not just for key words like “weekly” to find the ads that are out there with follow up that nips it in the bud. Monetary punishment can be a detriment to renting illegally, including agents who rent illegal units.


Pete Bacheler

Vacation rentals without proper licenses should be sought out, given red tags then taken to code compliance hearing before the special master and fined. The fine should increase if the homeowner continues to rent. If the property zoning does not allow vacation rentals the fine should be more severe as county/state sales taxes need to be paid.

Elizabeth Jolin

The Village recently purchased software to begin to manage this problem but it doesn’t seem to have been utilized to its fullest extent. The Council has to take responsibility for this by requiring its implementation and then requiring accountability from staff. Illegal rentals take away revenue from the Village, affect traffic patterns, quality of life, and diminish the affordable housing rental pool.


Casey Watkins

Build our influence at the state level to change the statue disallowing local governments to ban short-term rentals. HOAs have the ability in the language of their contracts to eliminate short term rentals in their associations. Anyone conducting vacation rentals and failing to register with the DBPR, should be fined the maximum allowed for each occurrence.

Henry Rosenthal 

It is essential to strengthen the ordinance and to aggressively enforce the law. Having purchased software from RentalScape, for $25,000, the following progress of enforcement is as noted:
From March 2021 to February 2022, $51,000 in fines have been issued. From March 2022 to present, $75,000 in fines have been issued. Thanks to the staff.

Deb Gillis

Deb Gillis

Raise fines. Follow up as to the effectiveness of the company being used. Publish the success rate for stopping the illegal activity. Success may be as simple as informing the owner of the law or as complicated as taking them to court. More success rate exposure will help curtail others. Utilize Monroe County and Tax Collectors efforts. Follow up on requiring Airbnb and others to provide client list. Investigate other avenues of identification besides advertisements.

John Timura 

John Timura

Triple the fines. Hire 2-4 more officers. Make a spreadsheet of advertised properties and cross reference the list to see who does not have a permit. Give each officer a list of properties to investigate. Serve violators through the legal process, and publish a list of names/ addresses in the local media, then follow the legal process. Use the revenue from violators to pay for the department. Surpluses can be directed to a new fund that could subsize workforce rents.

Angel Borden

Adjust value of homes “allowed” to rent. Give amnesty, help illegal homeowners get legal. Writing more tickets is “No Solution.” Help everyone go legal and pay taxes benefiting all the keys. Original rental restrictions protected motels and hotels and aren’t needed as “everyone has found the keys.” Home rental licenses dictated by area is confusing, outdated and unfair. This is not Cuba and if you sell your license should not be taken.


David Webb

Code Enforcement knocks on the door of a home owned by residents of Miami, two cars in the driveway with Wisconsin plates. Greeted with, “Oh, we’re not renting, we’re family.” The approach I have tried to take deals more with the negative impacts of the issue. Lost tax revenue to the County/State, noise and disruptive activity caused by renters. Islamorada resident’s “Right to quiet enjoyment of life” has to be aggressively protected.

Tom Rafanello

This is about enforcement, penalties, and ensuring everyone knows the Village will not tolerate illegal rentals. First, the Village must access its current ability to identify and enforce existing violations. Second, if insufficient, we should retain a third-party vendor that works for a percentage of collected fines. Finally, the penalties must be increased so that they cannot be viewed as a cost of doing business that is eclipsed by the rental rates. Strong enforcement works.

Sharon Mahoney 

The illegal vacation rentals is one of our biggest problems. The village paid for a software that was to help the situation… has it? We need larger fines , we need to look at the number of code enforcement officers we have on this issue, more officers or maybe make it the sole job for one or two. A program where there could be a call in by residents concerned a home is being used as an illegal rental we follow through having it checked out. Finally the fines need to be paid if not paid in a set time the fine goes up.

Jim McCarthy is a Western New Yorkers who escaped the snow and frigid temperatures for warm living by the water. A former crime & court reporter and city editor for two Western New York newspapers, Jim has been honing his craft since he graduated from St. Bonaventure University in 2014. In his 3-plus years in the Keys, Jim has enjoyed connecting with the community. “One of my college professors would always preach to be curious,” he said. “Behind every person is a story that’s unique to them, and one worth telling. As writers, we are the ones who paint the pictures in the readers minds of the emotions, the struggles and the triumphs.” Jim is past president of the Key Largo Sunset Rotary Club, which is composed of energetic members who serve the community’s youth and older populations. Jim is a sports fanatic who loves to watch football, mixed martial arts and golf. He loves to hit the links and play some softball with his Make A Play team. He also enjoys time with family and his new baby boy, Lucas, who arrived Oct. 4, 2022.