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

Vacation rental

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

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.


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.


  1. George

    I visited Key West back in the
    60s. Went to original Sloppy Joe’s. Is that the bar? Want to go back before I’m too old to travel. My wife and I are quiet people. Any ideas? Maybe we could rent a place near you. Promise no loud parties. Or cars parked in your space.

    • Linda Grist Cunningham

      Come on down. Start making plans for reservations and such now for next year!

  2. Todd

    I feel for you. I really do. Unfortunately, you live in a city that derives it’s revenue almost entirely from tourism. It has for 40 years. It only makes sense business and property owners would cater to this industry. This is the same in any tourist area around the country, Orlando, New Orleans, Deadwood SD, etc. The only way to avoid what you are experiencing is move to a bedroom community in a small town.

    • Linda Grist Cunningham

      Thanks, Todd, for the note. I do know you’re right about not being able to avoid the press of tourism. Key West was first and foremost a working town. Visitors began arriving with the completion of the Flagler Overseas Railway, then petered out as the economy tanked following the hurricane. The military was our biggest employer and most significant economic driver until the mid-1970s. So while we’ve always had tourists, it wasn’t until the 1980s that the most significant changes occurred to set the island on its path to becoming a tourist destination. So, yeah, we agree. I wish, though, that there were more “working town; real people” in the mix these days.

  3. Diane

    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.

    • Linda Grist Cunningham

      True. We could. But this is home.

  4. Bill

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

    • Linda Grist Cunningham

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

    • Davey B.

      We have owned and rented on Emma/ Front Street in Truman Annex every year since 1984. There are very few homes, townhouses or condos that aren’t rentals and, as I’m sure you know, if you have keys and pass through after 6pm it is incredibly quiet. By far the most quiet area on the island I have been.. I’d say the demographic of the renters in specific areas is more of the problem than the amount of rentals..

      • Linda Grist Cunningham

        Good point.

      • Mary

        My heart bleeds for you, not really. Try living on the Jersey shore with constant weekly rentals from May thug Sept. vacationers who think they’re entitled because they’re paying a fortune for a week, screaming kids and all. At least you have an off season with good weather(albeit hot) , here we’re suffering with frigid temps. I love KW but wouldn’t want it on a permanent basis.

  5. Dave Schiver

    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.

    • Linda Grist Cunningham

      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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