Key West Island News

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5 ways to avoid a Key West rental scam

by | 10/26/2018

The world of disappointment is littered with cliches. Sucker born every minute. Too good to be true. Key West has its very own: Ain't no sweet deals on vacation rentals in paradise.

High season starts the day after Christmas and for the next four months shivering mainlanders scour the internet looking for that sweet deal. Surely, if one looks hard enough one will find that perfect Key West cottage for the five-to-seven day excursion to the land of sun, sand and Hemingway.

Find it they do. Adorable little house with lush landscaping, a pool and all the trimmings, right smack in the middle of Old Town. Just look at those cute pictures, honey. Book it. Send the money. Get a receipt and a phone number. Head for Key West.

Oops. No house. Money gone. Police report. Deal-seeker scammed. Sigh.

A nice family of five showed up on my curb recently asking directions to the house they'd rented. Only the address didn't exist and the picture they had in hand matched a local resident's home -- definitely not for rent -- just up the street.

But we paid for it, they said. We even talked to the booking guy, but now he's not answering our calls. That's a too-familiar story in Key West, though dozens of vacation destinations know the drill, too. Report the scam to the local cops, alert the card company, get out another credit card, track down another place to stay and make one's way home. Poorer and a bit more enlightened about expecting something for nothing.

Be smart about your booking:

  1. Find a Key West rental company with a bricks-and-mortar location and a 305-area code. Check out the reviews. Call the local agent. There are plenty of reputable vacation rental companies in Key West. Many of the best are tied to local real estate companies. Craigslist and AirBnB aren't usually among them.
  2. Expect to pay top dollar. That means at least a couple-three hundred bucks a night for bare bones; double, triple and quadruple aren't unusual -- especially if you add on an Old Town location with pool, parking and space to maneuver.
  3. Plan to stay more than a couple nights. Most vacation home rentals in Key West require a minimum four-week stay. Local laws don't cotton to short-term rentals. If you want a quick trip, check out the hotels, inns and bed-and-breakfast accommodations.
  4. Be wary of offerings on websites like AirBnB where folks offer up their homes or a room to share. As great as they can be for some folks, Key West's ordinances don't allow local residents to rent out a room in their homes. Yes, you'll find some doing it. But unless they have a transient license and very few do, you're taking a significant risk.
  5. Check it out. Before you hand over your credit card, call the local chamber of commerce, the police or a local visitors center. They may be able to steer you away from a booking disaster.

Still, the best rule is the simple one: If it sounds too good to be true, it probably is.

(Originally published in 2014 -- but the message remains the same. If anything, rental scams have increased.)




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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