Executive Summary
Virginia Beach just made STR violations criminal misdemeanors with $1,000 fines, marking one of the harshest enforcement shifts in the U.S. New Orleans' Fifth Circuit ruling upheld the one-STR-per-block lottery system but struck down the corporate ownership ban, potentially opening a loophole for investors using multiple LLCs. Timmins, Ontario, launched mandatory online registration with a 4% accommodation tax and 60-day enforcement countdown. Dublin councils investigated 1,600 suspected illegal rentals over three years, with only 66 owners seeking proper planning permission despite over 1,000 active listings. San Diego's proposed Vacation Home Operation Tax could add $100-135 million in annual costs to whole-home STR operators, with a City Council vote coming October 22. Boulder approved festival-only licenses allowing up to 29 rental days per year for events like Sundance 2027, creating a new niche revenue opportunity.
New Regulations
Virginia Beach, Virginia, USA
Published: October 14, 2025
Regulation Category: Licensing
Summary: The Virginia Beach City Council has updated short-term rental regulations, reverting violations from civil infractions to criminal misdemeanors with fines starting at $1,000 for initial offenses and escalating to $2,000 for ongoing issues, effective immediately. Investors must obtain a zoning permit with a $500 annual fee (including $200 application), maintain $1 million insurance, provide parking, undergo inspections every five years, and remit a $2-per-night transient occupancy tax plus state lodging taxes monthly.
Source: Virginia Beach short-term rentals face criminal penalties for violations
Timmins, Ontario, Canada
Published: October 8, 2025
Regulation Category: Licensing
Summary: Timmins has rolled out a Granicus online platform for short-term rental owners to register as businesses, apply for annual licenses with pro-rated fees, and remit a 4% municipal accommodation tax on stays under 28 days, under a bylaw effective since January 2025. Enforcement starts within 60 days, enabling officers to track compliance in real-time, so investors should prioritize registration to avoid contact from bylaw officers and ensure seamless tax submissions.
Source: City launches online platform for short-term rental operators
New Orleans, Louisiana, USA
Published: October 7, 2025
Regulation Category: Zoning
Summary: The Fifth Circuit upheld most of New Orleans' 2023 short-term rental rules, including one STR per square block via lottery and on-site owner presence, but invalidated the corporate ownership ban as discriminatory, potentially allowing investors to use multiple LLCs to exceed ownership limits. The ruling affirms the city's regulatory authority while requiring permit numbers in ads, urging investors to consult on city responses and prepare for stricter enforcement on upheld provisions.
Source: Fifth Circuit rules on New Orleans' short-term rental laws
Dublin, Ireland
Published: October 13, 2025
Regulation Category: Zoning
Summary: Over the past three years, Irish councils, particularly in Dublin, have probed around 1,600 suspected illegal short-term rentals, with only 66 owners seeking planning permission since mid-2019 despite over 1,000 listings on platforms like Airbnb. Enforcement has primarily involved warning letters, but some owners face notices threatening legal action, signaling investors to verify compliance with local planning rules to avoid escalating penalties in high-pressure housing markets.
Source: Councils investigate 1,600 Airbnb-style lets suspected of planning breaches
Boulder, Colorado, USA
Published: October 10, 2025
Regulation Category: Licensing
Summary: Boulder City Council has approved a new festival short-term rental license allowing properties, including accessory dwelling units, to rent for up to 29 days per year during major events like the 2027 Sundance Film Festival, without the six-month residency requirement of standard licenses. Investors can hold only one license type at a time and must apply separately, providing an opportunity for event-driven revenue but with limits to prevent abuse in a market straining hotel capacity.
Source: Boulder Council Gives Final Approval to Festival Short-Term Rental License Ahead of Sundance
Developing Regulations
Magnetawan, Ontario, Canada
Published: October 13, 2025
Regulation Category: Occupancy
Summary: Magnetawan Township is reviewing potential updates to its short-term rental bylaw, including the possible elimination of the seven-day minimum stay requirement, which could open up more flexible booking options for property owners. This developing change aims to adapt to market conditions and address community concerns, potentially boosting occupancy rates but requiring investors to monitor council discussions for final implementation details.
Source: Magnetawan's short term rental bylaw set for key changes
San Diego, California, USA
Published: October 11, 2025
Regulation Category: Tax
Summary: San Diego's proposed Vacation Home Operation Tax targets whole-home short-term rentals and second homes not used as primary residences, potentially generating $100-135 million annually to fund public services amid a $258 million budget deficit. The measure heads to the City Council's Rules Committee on October 22, 2025, for ballot consideration, where investors should note it could increase operational costs while proponents argue it promotes fair housing contributions.
Source: Proposal to tax short-term vacation rentals could be headed for SD ballots