From Ordinance to Outcome: Optimizing Municipal Short-Term Rental (STR) Outreach
Most jurisdictions that regulate short-term rentals share a version of the same frustration: the ordinance exists, the violations are well documented, and yet short-term rental operators still fail to follow the rules. The issue is rarely the rules themselves, but the gap between identifying violations and communicating them to operators clearly, consistently, and at scale.
On April 22nd, Deckard Technologies hosted a live webinar to talk through exactly that gap, and what closes it. Garrett Lundberg, Solutions Consultant at Deckard, was joined by Bill Quincy, Code Compliance Manager for the City of Naples, Florida, for a candid conversation about what modern short-term rental Outreach looks like on the ground.
Naples, a coastal city in Southwest Florida with roughly 20,000 year-round residents, sees a major seasonal influx each winter. With restrictions on short-term rentals under 30 days across most residential areas, City staff faced growing challenges keeping up with online STR activity using traditional enforcement methods alone.
Bill Quincy, Code Compliance Manager for the City of Naples, has been with the city for 20 years and took over this role about three years ago. He joined the webinar to talk about what that journey actually looked like. A few things stood out from his side of the conversation.
|
1
|
You can't enforce a problem you can't define. |
Bill's team didn't have a reliable answer to a question they were regularly asked by council and residents: How many short-term rentals are actually operating in the city? They were counting dots on a map. To address that gap, the city launched a targeted Outreach campaign, sending formal notifications to suspected STR operators to clarify the rules and prompt compliance.
"The workload has gotten to be more productive." — Bill Quincy, Code Compliance Manager, City of Naples
Not less work, but better directed work. The first Rentalscape letter campaign gave his team a real number to work from and a defined list of properties to act on.
|
2
|
Accuracy is non-negotiable. |
Bill was direct about what happens when Outreach goes wrong. Contacting someone who isn't actually in violation doesn't just waste time — it damages your credibility with the community. A false accusation, he noted, can do more harm than a missed violation. Every match Rentalscape makes is backed by evidence, and that accuracy is what makes the Outreach defensible.
|
3
|
Educational first. Always. |
Naples has a zero-tolerance policy, but Bill was clear that the first letter is never a threat; it's information. Most operators aren't trying to evade compliance; they genuinely don't know what's required. Opening with education before escalating is both a better practice and better community relations.
|
4
|
The internet is dynamic. Your Outreach has to be too. |
A one-time letter blast isn't a strategy. New listings appear constantly. Properties go on and off platforms week to week. Without continuously tracking new listings and following up consistently, any progress quickly erodes.
"Having the series of letters ongoing and following up is way better than just a one-time mailing." — Bill Quincy
The audience questions focused heavily on the operational side of short-term rental Outreach, especially around maintaining accurate enforcement over time.
Why did Naples see an increase in listings in November?
Seasonal demand plays a major role in STR activity in Florida markets like Naples. Operators may temporarily activate listings around peak travel periods, especially ahead of the winter season, then remove them again shortly afterward. The discussion highlighted why ongoing monitoring matters: listings can appear and disappear quickly, making one-time Outreach campaigns difficult to sustain on their own.
Should Outreach begin with education before citations are issued?
Both speakers emphasized that educational Outreach is the best starting point. Garrett explained that the first letter is designed to clarify local regulations and encourage voluntary compliance before enforcement escalates. Bill added that Naples uses these early communications to walk operators through the rules and help resolve issues before formal action is necessary.
Does Outreach data hold up in legal proceedings?
Bill explained that Naples has successfully used listing advertisements, reviews, and rental parameters during code enforcement proceedings. Garrett noted that maintaining documented evidence and Outreach history helps establish a clear compliance record before cases move forward.
More than anything, the webinar highlighted a broader shift happening across local governments: successful STR enforcement is no longer just about writing regulations, but about building Outreach and enforcement workflows that remain scalable, accurate, defensible, and sustainable as the STR landscape continues to change week to week.
For jurisdictions trying to move from reactive enforcement to proactive compliance, that operational structure matters just as much as the ordinance itself. Deckard's Outreach tools are designed to help jurisdictions turn policy into measurable compliance outcomes.