83-year-old woman wins battle against $590,000 fine after home was mistakenly listed for rent

Spending more than five decades building a life in one home nearly ended for 83-year-old Honolulu widow Sandra May after a short-term rental listing appeared by accident on her property. That was the reality for 83-year-old Honolulu widow Sandra May, whose property became the center of a legal battle after a short-term rental listing appeared by accident.

May had lived in the same home for 56 years and rented out an attached apartment to help manage her living expenses. However, a technical error caused the unit to appear available for short-term stays, leading the city to issue a massive penalty that threatened everything she had built.

According to Fox News, May was recovering in the hospital after a serious car accident when the city’s notices were sent. Because she did not respond in time, the fines continued to grow until they reached nearly $590,000.

A simple online mistake almost cost her the home she spent 56 years protecting

Honolulu regulations prohibit residents from advertising or renting properties for stays under 30 days outside approved resort areas. After the listing appeared, the city imposed a $10,000-per-day fine and eventually placed a lien on May’s property. The penalties also affected her ability to renew her driver’s license and vehicle registration.

Unexpected property disputes can sometimes leave owners dealing with consequences they never saw coming. In another unusual case, a New York farmer said authorities asked him to pay to remove an abandoned ATV that someone else had left on his land. 

May’s attorneys from the Pacific Legal Foundation argued that the apartment was never offered for illegal short-term rentals. They claimed the listing issue came from a glitch on the hosting platform. Her team explained that the daily rate was included only to help calculate costs if a guest extended a legal 30-day stay.

May later filed a federal lawsuit against Honolulu, which resulted in a settlement that reduced her fine by 95 percent. Attorney Loren Seehase argued that penalties should match the actual violation instead of becoming an amount that could force someone to sell their home.

Under the agreement, Honolulu will place a $30,000 civil lien on May’s property. However, the city will not pursue foreclosure during her lifetime. The amount will be handled through escrow if she sells the home or collected after her death through foreclosure.

A city spokesperson said the reduced penalty considered May’s age, medical situation, long connection to the property and limited involvement in the listing mistake. May said she never believed she had broken the law and expressed relief that the case was finally resolved.

The case has gained attention across Hawaii, where officials have issued more than $90 million in short-term rental fines across Oahu. Her legal team says the settlement highlights the need for limits on excessive government penalties.