Key Takeaways
- An 83-year-old Oʻahu homeowner faces $600,000 in fines for allegedly advertising her unit as a short-term rental in error.
- Honolulu’s 2019 law allows fines of up to $10,000 per day for advertising an illegal STR, even without a completed booking.
- Operators should audit platform settings regularly — a platform-side error does not automatically protect hosts from municipal fine liability.
An 83-year-old Hawaii woman is now facing a jaw-dropping $600,000 in fines over a rental listing she says she never meant to run illegally.
The Oʻahu case is putting a spotlight on just how fast short-term rental enforcement can spiral, especially for property owners who may not realize they have crossed a local regulatory line.
According to Hawaii Public Radio, Sandra May filed a federal lawsuit Thursday challenging the fines issued by the City and County of Honolulu.
May had rented out her one-bedroom unit in Wilhelmina Rise to long-term tenants since the 1970s, but turned to an online vacation rental platform in 2019 after struggling to find a new renter.
The lawsuit describes May as “technologically illiterate,” adding another wrinkle to a case that could hit close to home for older owners, accidental hosts, and anyone trying to navigate increasingly complex STR rules.
Honolulu’s STR advertising laws
Honolulu passed a law in 2019 allowing fines solely for advertising an illegal short-term rental — with penalties of up to $10,000 per day the listing remains online. S
TR regulations outside resort zones are an absolute ban on Oʻahu, and May’s unit sits outside any resort-zoned area.
She received a first notice, worked with the platform to restrict bookings to stays of 30 days or longer, then received a second violation in 2021 despite making no changes herself.
Related: DEA searches Ohio STR tied to zoning lawsuit
“That’s why we’re headed to court, so that the court can assess whether the fine imposed against Sandra is grossly disproportionate to an accidental advertisement,” according to May’s attorney, Loren Seehase of the Pacific Legal Foundation.
The platform reportedly acknowledged the renewed availability was an internal error on its end, yet the city still allegedly demanded payment and filed a lien against May’s property last year when she couldn’t pay.
