83-year-old wins settlement after Honolulu slapped her with $590K fine over website glitch

An 83-year-old widow can keep her Honolulu home after reaching a settlement with the city over nearly $600,000 in fines stemming from what she says was an online rental listing error.

Sandra May, a retiree, rents an attached apartment on her property to supplement her fixed income. After her rental unit was accidentally advertised online as available for short-term stays, the city fined her $10,000 a day for nearly two months.

Because May was hospitalized following a serious car crash, she did not initially see the city’s notices, allowing the fines to balloon to $590,000. Under Honolulu ordinances, it is illegal to rent or advertise residential properties for periods of less than 30 days outside designated resort zones.

Attorneys representing May from the Pacific Legal Foundation argued the unit was never actually available for short-term stays and that the listing stemmed from a website glitch on the hosting platform. Despite efforts to resolve the issue, the city placed a lien on May’s home, blocked her from renewing her driver’s license and vehicle registration and told her to “get an attorney.”

May filed a federal lawsuit against the city and recently reached a settlement that reduces her total fine by 95%, allowing her to remain in the home where she has lived for 56 years.

“Winning this case is an enormous relief because it resolves all of the city’s violation charges and excessive fines,” May told Fox News Digital. “While the case ended in a settlement, I don’t personally feel guilty of doing anything wrong.”

May said her rental listing included a daily rate alongside a minimum 30-day rental so that if a guest wanted to stay longer than a month, it would be easier to calculate the extra days.

“To me, that was simply common sense,” she added. “The city viewed it differently, but I never believed I was violating the law.”

May added that she was grateful to God and her legal team at the Pacific Legal Foundation for stepping in at “the lowest point in [her] life.”

Loren Seehase, an attorney with the Pacific Legal Foundation, said the settlement resolves all of May’s outstanding charges, including three additional violations the city issued after the organization became involved in her defense.

“Under the Eighth Amendment, fines must be proportionate to the alleged offense, not whatever the government thinks it can get away with demanding,” she said in a statement. “This outcome reaffirms that principle and ensures Sandra can keep her home, which the City’s initial demands would have forced her to sell.”

Scott Humber, communications director for the City and County of Honolulu, confirmed that May agreed to a reduced penalty of $30,000. Under the terms, the city will record a $30,000 civil fine lien against her home, but will not initiate foreclosure during her lifetime. The fine will be paid through escrow if she sells the property, or through foreclosure following her death.

Humber noted that the settlement factors in May’s age, her medical hardships, her decades residing at the home and her “limited personal involvement in creating her advertisement.”

As part of the agreement, May dismissed her federal lawsuit and agreed to withdraw her administrative appeals.

“The Department of Planning and Permitting takes short-term rental violations seriously and imposes significant fines for such violations,” Humber said in a statement. “Fines for advertising a property as an unpermitted short-term rental on Oahu are typically $10,000.00 per day.”

“However, the Department may not have all of the relevant facts at the time of determining the daily fine rate for a particular violation and may adjust the total daily based on factors that become known to the Department after a fine has been assessed,” the statement continued. “After performing this review and learning of Ms. May’s unique circumstances, the Department was able to reach an agreement with Ms. May on the appropriate penalty for her conduct.”

May’s attorneys said her case highlights a broader issue on Oahu, where the city has issued more than $90 million in fines for similar rental advertising violations.

Seehase told Fox News Digital the settlement “sends a clear message to Honolulu and municipalities across the country” that “governments cannot impose crushing financial penalties without constitutional limits.”

“No homeowner should face losing their home over penalties that are grossly disproportionate to the alleged violation,” she said.