The Key West Mystique

Key West Island News


Key West Island News connects Key West residents and friends of the island, fosters our One Human Family culture and advances understanding of shared goals for our island community

Real Key West

Key West vacation rentals | 5 takeaways from the community workshop

By Linda Grist Cunningham, editor and proprietor

Linda Grist Cunningham is editor and proprietor of Key West Island News and KeyWestWatch Media LLC. She and her husband, a park ranger at Fort Zach, live in Key West with their Cat 5s.


By the time last Friday that I got around to watching Thursday’s three-plus-hour community workshop on Key West vacation rentals, I knew these things for sure: No one set fire to city hall. The EMTs didn’t show up and no one was arrested. From all accounts, the vacation rental workshop was a most civilized affair.

Actually, it was. Civilized that is. Shockingly so, perhaps, given the volatile subject matter. A lot of Key West loves hating on vacation rentals about as much as they enjoy hating on cruise ships. But there it was on a three-hour video. Civilized. Most unexpected in these days of hair-trigger vitriol and cancellation.

There were a hundred or so locals, mostly connected to Key West real estate in some fashion (think homeowners, landlords, real estate agents, property managers, financial types and a flock of second-home owners who zoomed in (pun intended)) taking turns speaking, nary a raised voice, much less a fist, making points and nodding or shaking heads politely depending on points being made.

It was so fascinating to watch the old-fashioned respect among folks of differing minds that I almost forgot why I was willing sit through the video in the first place. I knew a bunch of the folks in the room and actually texted them as I watched to thank them for making good, albeit, perhaps, unpopular points.

The City Commission called the special workshop for Thursday, Sept. 8, to let the community vent over a proposed ordinance that kinda, sorta, absolutely did get slipped into the commission agenda for approval without a shred of community input.

The ordinance would have forbidden any homeowner who did not have the appropriate Key West vacation rental business tax receipt in placed by May 3, 2022, from ever renting their home for less than six months. Even I went into “Mary, Joseph and the Wee Donkey What Were They Thinking?” outrage mode over that one.

Key West vacation rentals
Fort Zachary Taylor State Park | The peninsula at sunset is a reminder that we do, indeed, live in Key West. And that’s worth the work.

I mean, I have no intention of turning my home into a vacation rental, but, seriously, I’m hard-pressed to figure out how that proposed wording isn’t some egregious property rights grab. Almost 600 local homeowners apparently have already been down to City Hall to get their business tax receipt just to “be on the safe side.” I haven’t, but maybe I’m thinking about it. Keeping options open, you know?

Anyway, there was some serious blow back to what a whole lot of folks considered an end run on vacation rentals and property rights. Smarter political heads on the city dais called the workshop and promised a revisiting of the ordinance. I did hear folks near the end of the video asking the city folks to promise that the May 3 deadline would disappear NOW. I suspect it already has, at least in principle. And, the mayor has promised more listening and talking before any ordinance makes it way to a vote.

Key West vacation rentals: Five takeaways

While its civility was noteworthy, more important were the key takeaways from the workshop. Here’s what I heard:

  • We are conflating a myriad of community woes and assigning blame to a vague definition of vacation rentals. As a community, we are staggering under an unsustainable load that includes skyrocketing home and long-term rental prices; our increasingly hollowed out middle class; a deteriorating, umbilical cord infrastructure that leaves us at the mercy of winds and water; and a culture shift from small hometown to mega destination. We are flummoxed at finding solutions; it’s easier to just blame vacation rentals — or cruise ships, for that matter. Are they part of the problem? Of course. Are they all of it? Hardly. Must they be part of the solution? Yes.
  • We don’t share the same definitions of vacation rentals. We tend to lump together (1) locals who rent their primary residences out for a month or two; (2) snowbirds; and, (3) second home owners who don’t rent their homes into the same bucket with investor-style LLCs that have but one purpose: Buy, renovate, rent for high dollar and flip post profit. If we’re to find an equitable solution, we’re going to need broadly understood vacation rental definitions.
  • We don’t really know the numbers. Oh, there were lots of numbers tossed around during the workshop, but their sources need to be bolstered by local, feet-on-the-ground research. Online fee-based data crunchers like AirDNA, which claims it tracks 10 million rentals across the country, and which the city used to show vacation rentals in Key West, pulls from publicly available sources and makes predictive analyses for a fee. Are they right? Perhaps. But until the city has its own data about who owns what, who rents what, when and where, we won’t know.
  • We aren’t enforcing the current vacation rental laws. One statement at the workshop brought a consensus of applause, nodding heads and even cynical laughter: Everyone knows who’s breaking the laws in every neighborhood and the city does nothing about it. Enforce the rules. Fine, really fine, those who happily consider our paltry fines the cost of doing business.
  • There was no one in that room who isn’t part of this community, who doesn’t understand the challenges. These are our neighbors; they live with the same frustrations. Though, there were one or two in the out-of-town Zoom group who kinda missed the points.

I came away from the workshop in a darn upbeat frame of mind. We need better management of our vacation rental landscape. That is clear. But we need to understand that even were we to magically turn every vacation rental and second-home property into housing for locals, our real challenge remains: We miss our sense of community.

Perhaps we need my mother’s reminder: “But you live in Key West. Now, go do something to make your island home better.”


Pin It on Pinterest