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Living in Key West: How long before vacation rentals overtake my neighborhood?

by | 03/23/2021

I live on the quietest block on the quietest street in the quietest neighborhood in Key West. Now that the Conch Train has been re-routed, hours can pass without a car and there’s only the occasional nocturnal, rowdy visitor wandering back to the hotel.

It’s so quiet I can hear the idiot with that ridiculous train horn clear across the island. It’s so quite I can hear Evening Colors at sundown from the Navy out at the waterfront. It’s so quiet I feel the need to apologize to the neighbors when Cat 3 (Jersey) and Cat 5 (Michael) do that darn drama queen screeching over some imagined territorial slight. It’s so quiet happy hour guests know what I mean when I say “inside voices, please.”

The question is, though, how long will it last? Inexorably my block will fall to the rapacious demand for vacation home rentals that has crept steadily from Old Town proper into the surrounding residential neighborhoods. Bahama Village, the Meadows, the Casa Marina District and Midtown are shifting — and New Town won’t escape.

Vacation home rentals change the tenor of our residential neighborhoods. Old Town is a lost cause, I’m afraid. Transient and monthly vacation rentals, the proliferation of houses-turned-commercial and second-home owners who aren’t in-house much of the year have combined over a couple decades to turn Old Town into a visitors’ vacation district, leaving behind so much of its residential feel.

With apologies to my real estate friends, I cringe when I see “right in the middle of everything that makes Key West magical” in a real estate listing for a single family house in Old Town. That’s not a home; it’s a vacation rental in the making.

There’s little to be done with transient rentals. Those are the houses, condos and rooms that are licensed to rent for a day or two or a week or so. More hotel than home. There are only so many transient licenses out there and no more are being issued. So, except for the games people play with them (that’s for another day), if you’re living next door to a transient rental, well, good luck.

It’s the monthly rentals, which require no license, that shift our neighborhoods. Not all monthlies, mind you. There are plenty of wonderful visitors living peacefully in my neighborhood. And, as much as I wish they were year-round residents, I’ve accepted the good folks who spend a month or two living among us.

But. When a monthly rental becomes a revolving door during the month, when there’s no such thing as “inside voices” during a profanity-laced party at midnight, when cars are parked willy-nilly and left in residential spaces for days on end, when there’s no property manager acting on complaints — and when code enforcement is so strapped it can’t do anything — well, that’s not a neighborhood long-term residents want to live in anymore.

Key West’s city commissioners in 2003 thought they were reining in rentals with an ordinance that said:

“The city commission finds that short-term or transient rentals affect the character and stability of a residential neighborhood. The home and its intrinsic influences are the foundation of good citizenship; although short-term tenants no doubt are good citizens generally, they do not ordinarily contribute to activities that strengthen a community. Therefore, the city intends by these regulations to establish a uniform definition of transient living accommodations, and to halt the use of residences for transient purposes in order to preserve the residential character of neighborhoods.”

In 2003, Key West implemented new rules in an attempt to clean up transient rental abuse and manage the nascent vacation rental market. They’re pretty benign: You have to have a transient license to rent your property by the day or week; you can rent your space for a month without a license. Both require a minimal fee and minimal “business tax receipt” license. Technically, you’re supposed to pay the bed tax. There are penalties for disregarding the rules, though enforcement is too often spotty. And, of course, there’s a thousand and one ways for scofflaws to be creative.

That 2003 date is important because Florida legislators remain hellbent on preempting control of vacation rentals across the state. Each year legislation that would overturn local ordinances wends through the Florida legislature and each year it gets one step closer to passage. This year as in years past, there’s a carve-out that grandfathers Key West’s local control. Ordinances in place before 2011 have been — so far — exempt from state takeover. I’m not holding my breath that state takeover won’t happen.

I usually try in my last paragraphs to come back around to a more uplifting ending. Kinda hard to do with this one.

Linda Grist Cunningham

Proprietor & Editor

Linda Grist Cunningham is proprietor and editor of KeyWestWatch Media LLC and Key West Island News. She is a nationally recognized legacy newspaper editor and publishing executive with more than 40 years of professional experience.

Cunningham is a veteran journalist who relocated to Key West in 2012, when legacy media proved itself too cumbersome to change with and adapt to today’s information world. She built her new media company business plan, packed up four cats (now the Cat 5s) and a husband and launched her digital solutions company for small businesses and not-for-profits. Key West Island News went live in 2018.

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  1. You shouldn’t have to put up with those noisy intrusive tourists. It’s your neighborhood and you should be able to live in peace.
    Sell it and move out to a nice quiet place on the mainland.

    • True. We could. But this is home.

  2. It totally screw my hood on the 11 block of Whitehead slowly but surely rentals and guest house took over

    • I know a lot of us share that experience. It makes it hard to build a neighborhood.

  3. Sounds like a case of “I got mine, now shut it down so no one else comes in!”. We’ve been “Intruding” in your neighborhood’s for 12 years. Seems no one one has an issue taking my money. I’m glad the friends we have made over the years aren’t as elitist as you.

    • Dave, that wasn’t my intent at all. None of us are unwelcoming to the folks who come here with shared respect for our community and our neighborhoods. What we lament are the disrespectful renters who either don’t know or choose to disregard that this is our home. I can’t imagine a time when anyone would be happy to have houses in their neighborhoods become rowdy, careless party places.


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