As millions of visitors prepare to descend on Florida for Spring Break 2026, local governments are bracing for the annual surge in short-term rentals (STRs). But this year, many municipalities are running into a growing challenge: the visibility gap.
With fragmented regulations, high-rise density, and rapid-fire listings overwhelming traditional enforcement tools, counties and cities are increasingly finding themselves with a blind spot, unable to identify, track, and enforce STR regulations in real time.
Here is a look at why this gap exists, and how local governments can close it before the peak tourism season hits.
Florida is not just a popular destination; it is the single largest and most complex short-term rental market in the United States.
Consider the numbers from 2025 alone:
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Florida is not just another market, but the benchmark, according to Nick Del Pego our CEO. He notes that when you combine the largest inventory in the country with seasonal surges and fragmented local control, you create an environment where traditional tools simply cannot keep up.
Following Gov. Ron DeSantis' veto of Senate Bill 280, Florida remains governed by a patchwork of local ordinances rather than uniform statewide preemption. The City of Naples maintains a strict ban on rentals under 30 days, Monroe County focuses heavily on tax compliance, and the City of Holmes Beach prioritizes nuisance enforcement.
Because every jurisdiction is different, a one-size-fits-all compliance platform simply does not work. The enforcement challenge ultimately boils down to two major hurdles:
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The Vertical Blind Spot: |
Florida’s landscape of high-rise condominiums creates massive challenges for legacy data-scraping tools, which often fail to pinpoint specific units within large, vertically stacked buildings.
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Flash Listings: |
At Deckard Technologies, we believe local governments should not have to tolerate enforcement blind spots during their busiest season. That is why we have developed a system powered by a proprietary artificial intelligence engine that relies on forensic identification.
By scanning daily rather than weekly and incorporating computer vision, our system detects the flash listings and vertical units that conventional vendors miss. We pair this with 24-hour hotlines that empower residents to report noise, trash, and other violations in real time.
Del Pego explains that Deckard does not create new data. Instead, the team organizes and analyzes what is already public, functioning less like a filing system and more like a tech-first investigator.
Our technology is already making a measurable difference across the state:
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As part of our ongoing efforts to educate jurisdictions nationwide, Deckard is hosting an exclusive webinar featuring City of Naples Code Compliance Manager Bill Quinsey and Deckard Solutions Manager Garrett Lundberg.
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From Ordinance to Outcome: Optimizing Municipal STR Outreach Date: Wednesday, April 22, 2026 |
Your community's public trust relies on fair, consistent enforcement. Let us help you catch the invisible inventory.