Homesharing in HOAs What Concerns Boards and How to Handle It

On any given day or night in Chicago, a stranger walks up to Craig Perry’s North Lawndale home, opens Perry’s door, hangs up his or her jacket, and relaxes in Perry’s bed while watching Perry's television and using his WiFi, before disappearing again without a trace. In a few days or weeks, the pattern repeats itself with another stranger, and another after that.

The parade of outsiders pleases Perry, 54, to no end. It’s thanks to these strangers that he was able to stop working as a computer consultant—and instead, is able make an income renting out his spare three-bedroom, one bathroom apartment in his brick two-flat via Airbnb Inc. He doesn’t plan on going back to his day job anytime soon—or stopping the rotating cast of travelers passing through his apartment. “There were hardships at the place I was working for, and I found that this was a wonderful alternative,” Perry says.

An Ideal Idea?

The media and political buzz surrounding so-called “home share” or “short-term rental” websites (primarily Airbnb, but also other similar services like or has been on the upswing over the last year or so. It sounds like a perfect arrangement; You go on vacation, and rent out your home while you’re gone—you get a house sitter who pays real money, instead of the other way round. Or, you stay home, and rent out your spare room—making a few hundred (or even a few thousand) dollars without doing anything more than washing your extra set of sheets and wiping down the counters. It’s all part of a growing trend called homesharing, which is taking Chicago (as well as other “destination cities”) by storm.

In the Chicago-area, you can rent anything from a “quiet place in Wicker Park” that the owner describes as a spare room with some storage and a fold-out bed for $45 per night to a $3,000 Lakeview luxury high-rise with a big-screen theater projector, a 24-hour business center and a full gym. Indeed, for renters and for those doing the renting, when it comes to homesharing, the sky's the limit in terms of what you can get for your money, and how much cash you can make.

But while thousands of apartment owners in cities like Chicago, New York, Boston and San Francisco love being able to monetize their units by renting an extra bedroom (or even their whole place, if they're out of town) to a visitor or tourist, condo and HOA boards and management are typically less enthused about the trend. A constant stream of non-resident visitors raises security concerns, adds wear-and-tear to common areas, and complicates the enforcement of house rules. Depending on the city, short-term rentals may also run afoul of zoning and hospitality laws.


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