01 - The Challenge

Enforcing STR restrictions without visibility

For the City of Naples, the challenge was not a lack of regulation. It was a lack of visibility.

Naples is a city of roughly 20,000 residents in Southwest Florida, located within Collier County. During peak winter season, the broader county sees nearly 100,000 seasonal residents and visitors between December and April, increasing pressure across the region. As short-term rental activity expanded across online booking platforms, enforcement became increasingly difficult to manage using traditional methods alone.

In the City of Naples, short-term rentals fall under the legal definition of “Transient Lodging Facility,” which includes any property rented for periods of less than 30 days, either through repeated short stays or by being advertised as such. Under the City’s Code of Ordinances, this type of use is prohibited in residential zoning districts and limited to specific commercial areas, making short-term rentals effectively restricted across most of the city. On paper, enforcement should have been straightforward. In practice, it was not.

Before adopting a more structured approach, the Code Compliance team relied on manual processes to identify violations. Staff searched booking platforms individually, reviewed listings one by one, and attempted to determine whether a property was actively renting.

02 - The Solution

From reactive enforcement to structured Outreach

To address these challenges, the City of Naples partnered with Deckard Technologies, leveraging its Rentalscape platform to gain visibility into short-term rental activity and identify potential violations at scale.

The shift began with a simple but critical step: identifying the full scope of potential violations and addressing them systematically. Instead of handling cases individually, the City launched a structured Outreach campaign through the Rentalscape system, targeting properties advertising rentals under 30 days. The first wave alone reached hundreds of properties, followed by ongoing monthly Outreach. 

This approach is reflected in the Outreach data. The initial Outreach effort began with 282 letters sent in a single month to properties identified as potential STR violations, notifying owners of the City’s regulations and compliance requirements. In the months that followed, the number of follow-up notices declined as more properties came into compliance or removed their listings. Over time, a smaller subset of properties required additional follow-up, with 125 receiving a second notice (See Figure 1)

03 - Results

A measurable reduction in STR activity

Following the implementation of structured Outreach efforts, the City of Naples reported a 30–40% reduction in active STR ads and non-compliant activity. During the initial Outreach campaign alone, 128 properties were removed from active violation status after receiving notices.

As outreach efforts continued, the City also observed a sustained decline in publicly visible STR listing activity (See Figure 2).

A lot of people just corrected that part right away. We didn’t have to spend any time chasing it down."

— Bill Quinsey, Code Compliance Manager, City of Naples.

"Rather than just looking at a map… we have the actual address. We can go right to that property."

 

Bill Quinsey, Code Compliance Manager, City of Naples.

Instead of guessing where to act, the team could prioritize properties showing clearer signs of ongoing activity, helping staff allocate time and resources more effectively.

"It definitely helped us narrow down our scope of work and figure out the context of the problem."

 

Bill Quinsey, Code Compliance Manager, City of Naples.

With an improved view of STR activity, enforcement evolved from a reactive process into a more consistent and informed approach to long-term compliance.

04 - What's Next

Sustaining compliance at scale

With greater visibility into STR activity, the City of Naples has shifted from reactive enforcement toward a more proactive and data-informed approach to long-term compliance. What began as a focused Outreach campaign has evolved into a more consistent and sustainable enforcement strategy.