The advent of the share economy and its concomitant innovation has presented numerous regulatory challenges for all levels of government. Legislation and regulation typically lag far behind technological and societal development, often resulting in reactionary policies to address new challenges and opportunities. Short-term rentals are a prime example. We have seen the explosion in popularity of individual homeowners or investors utilizing popular websites to rent out rooms, single-family homes, and apartment units for short periods of time, often resulting in significant income to the property owners. This change often results in impacts to neighboring property owners and the community at large. Many local codes have not kept pace with these developments. We will discuss these short-term rentals, the efforts to regulate them, case law interpreting such efforts, and tips on fashioning regulation.