An 83-year-old widow will retain ownership of her Honolulu home following a settlement with the city that significantly reduced a nearly $600,000 fine. The substantial penalty originated from what her legal team described as an accidental online rental listing error.

Sandra May, who relies on renting an attached apartment on her property to supplement her retirement income, was fined $10,000 daily for almost two months. The city's fines were levied after her rental unit was erroneously advertised online for short-term stays. Honolulu ordinances prohibit renting or advertising residential properties for periods shorter than 30 days, except in designated resort zones.

May's hospitalization after a car accident meant she initially missed the city's notices, allowing the fines to escalate. Attorneys from the Pacific Legal Foundation, representing May, contended that the unit was never actually available for short-term rentals and that the listing resulted from a glitch on the hosting platform. Despite attempts to resolve the issue, the city placed a lien on May's home, blocked her driver's license and vehicle registration renewals, and advised her to seek legal counsel.

May filed a federal lawsuit against the city, and the recent settlement resolves all outstanding charges, reducing her total fine by 95%. Under the terms of the agreement, May will pay a reduced penalty of $30,000. The city will record a civil fine lien of $30,000 against her property, with the condition that foreclosure will not be initiated during her lifetime. The fine is to be paid through escrow upon sale of the property or through foreclosure after her death.

“Winning this case is an enormous relief because it resolves all of the city’s violation charges and excessive fines,” May stated. She explained that her rental listing included a daily rate alongside a minimum 30-day rental period for ease of calculation for longer stays, which she considered common sense. “The city viewed it differently, but I never believed I was violating the law,” she added.

Loren Seehase, an attorney with the Pacific Legal Foundation, emphasized that the settlement upholds the Eighth Amendment's prohibition against disproportionate fines. “This outcome reaffirms that principle and ensures Sandra can keep her home, which the City’s initial demands would have forced her to sell,” Seehase said.

City and County of Honolulu communications director Scott Humber acknowledged that the settlement takes into account May's age, medical hardships, long residency at the home, and her limited personal involvement in creating the advertisement. The city's Department of Planning and Permitting typically imposes fines of $10,000 per day for advertising unpermitted short-term rentals. Humber noted that the department may adjust fines based on newly acquired facts and that in May's case, a review of her circumstances allowed for an agreement on an appropriate penalty.

Attorneys for May highlighted that her case is representative of a broader issue on Oahu, where the city has issued over $90 million in fines for similar rental advertising violations. They stated the settlement sends a message to municipalities that financial penalties must have constitutional limits and that homeowners should not face losing their property over penalties disproportionate to the alleged offense.