Honolulu, Hawaii — An 83-year-old widow has secured a major legal victory after reaching a settlement with the City and County of Honolulu that dramatically reduced nearly $590,000 in fines stemming from what she says was an online rental listing mistake. The agreement allows Sandra May to remain in the home she has lived in for more than five decades while ending a legal battle that raised questions about excessive penalties and government enforcement.
Online Listing Error Triggered Massive Daily Fines
Sandra May, a retired homeowner, rents an attached apartment on her property to help supplement her fixed income.
According to court filings, the city alleged that her rental unit had been advertised for short-term stays, which violates Honolulu’s rules prohibiting rentals of less than 30 days outside designated resort areas.
The city imposed $10,000-per-day fines that continued for nearly two months, causing the total penalty to climb to approximately $590,000.
May’s legal team argued that the apartment was never actually available for illegal short-term rentals. Instead, they said the listing resulted from a website glitch that mistakenly displayed the property as eligible for shorter stays.
May later explained that she included a daily rate only to help calculate costs for guests staying longer than the required 30-day minimum.
She said she never believed she was violating local law.
Hospitalization Prevented Her From Responding
The situation became even more complicated because May was recovering from serious injuries following a car crash when the city began sending violation notices.
According to her attorneys, she did not initially receive or respond to those notices because she was hospitalized, allowing the daily penalties to continue increasing.
As the fines accumulated, the city placed a lien on her home, prevented her from renewing her driver’s license and vehicle registration, and advised her to seek legal representation.
Facing the possibility of losing the home where she had lived for 56 years, May filed a federal lawsuit challenging the city’s actions.
Settlement Reduces Fine by 95%
After months of litigation, both sides reached a settlement that significantly reduced the financial penalty.
Under the agreement, May’s total fine was lowered to $30,000, representing a 95% reduction from the original amount.
The city confirmed that the $30,000 civil fine will remain as a lien against her property, but officials agreed not to pursue foreclosure during her lifetime.
If the home is sold, the fine will be paid through escrow. Otherwise, it could be recovered after her death under the settlement terms.
In exchange, May agreed to dismiss her federal lawsuit and withdraw her administrative appeals.
Attorneys Say the Case Reinforces Constitutional Limits
May said the settlement brought tremendous relief after months of uncertainty.
She maintained that she did nothing wrong and thanked both God and her attorneys at the Pacific Legal Foundation for helping her through what she described as one of the lowest points in her life.
Her attorney, Loren Seehase, said the agreement reinforces an important constitutional principle that government fines must be proportionate to the alleged offense rather than financially devastating.
City officials said they considered May’s age, medical hardships, decades of residency, and limited role in creating the online advertisement before agreeing to reduce the penalty.
They also emphasized that Honolulu continues to treat illegal short-term rental advertising seriously, noting that $10,000-per-day fines remain the standard penalty for such violations.
According to May’s legal team, the case also highlights a broader enforcement issue on Oahu, where authorities have issued more than $90 million in fines for similar rental advertising cases.
What do you think? Should cities have greater flexibility when honest mistakes lead to massive financial penalties, or should strict enforcement remain in place? Share your thoughts in the comments below.
