Executive Summary
Sausalito, California, is actively enforcing a short-term rental ban with fines up to $5,000 for repeat violations, requiring immediate removal of all listings under 30 days. San Diego's rules committee approved a proposal for a $5,000 annual tax per bedroom on short-term rentals and second homes, potentially affecting over 10,000 properties and generating $135 million yearly if the full council votes yes. Maui County is moving forward with Bill 9, which could convert 6,000 of the island's 15,000 short-term rentals into long-term housing, with a council vote expected in November. On the positive side, New York City Council is considering amendments that would allow homeowners to host up to four guests instead of two and permit locked-off private areas without physical presence, potentially easing current restrictions. Vail, Colorado, voters will decide in November on a 6% tax increase on short-term rentals to fund housing initiatives, with Airbnb contributing $30,000 to opposition campaigns. Village of Holly, Michigan, capped total short-term rental licenses at 50 for approximately 35 existing properties, with annual renewals on a first-come, first-served basis and no guarantee of year-to-year approval.
New Regulations
Sausalito, California
Published: October 23, 2025
Regulation Category: Zoning
Summary: Sausalito is enforcing a strengthened short-term rental ban by fining owners up to $5,000 for third violations of advertising rentals under 30 days, with recent identification of dozens of infractions including 16 in the past month. Short-term rental investors must immediately remove listings from platforms like Airbnb and VRBO, as the new rules close loopholes like minimum stay settings near 30 days.
Source: Sausalito readies enforcement of short-term rental ban
Town of Essex, Ontario, Canada
Published: October 26, 2025
Regulation Category: Licensing
Summary: The Town of Essex is notifying short-term rental property owners that initial three-year licenses are expiring and must be renewed under a revised bylaw that shortens the license term to one year with a $500 annual fee. Investors need to schedule fire inspections if not completed in the last three years to ensure compliance and avoid delays in renewal approval.
Source: Essex reminds short-term rental unit owners to renew
Village of Holly, Michigan
Published: October 22, 2025
Regulation Category: Licensing
Summary: The Village of Holly Council unanimously approved Ordinance 475, requiring short-term rental owners to register properties as businesses and renew licenses annually on a first-come, first-served basis, capping total licenses at 50 for the village's roughly 35 existing STRs. Investors with existing operations must cease non-compliance and complete paperwork, noting that licenses are not guaranteed year-to-year even for current holders.
Source: Village of Holly approves short-term rental ordinance
Glynn County, Georgia
Published: October 23, 2025
Regulation Category: Licensing
Summary: Glynn County is introducing a new online platform starting November 1 for managing short-term rental certificates, simplifying the process for obtaining or renewing them. This update benefits short-term rental investors by reducing administrative hurdles and processing times without altering core requirements.
Source: County streamlines process for short-term rental certificates
Developing Regulations
New York City, New York
Published: October 25, 2025
Regulation Category: Licensing
Summary: New York City Council Member Mercedes Narcisse has introduced Intr. 948A to amend Local Law 18, proposing to allow one and two-family homeowners to host up to four guests (up from two), exclude children from guest counts, and permit hosts to lock off private areas without being physically present during stays. Short-term rental investors should note that these changes, supported by Airbnb, aim to help Black homeowners maintain properties and counter predatory investors, potentially increasing operational flexibility if passed.
Source: Council member aims to ease Airbnb, Vrbo restrictions for homeowners
Vail, Colorado
Published: October 25, 2025
Regulation Category: Tax
Summary: Vail voters will decide in November on Issue 2A, proposing a 6% tax increase on short-term rentals to fund housing initiatives, with opposition backed by Airbnb's $30,000 contribution amid campaigns raising over $69,500 against it. Short-term rental investors, noting that one-third of residential units are STRs, should monitor the vote as the tax would apply without curbing operations but could raise costs if approved.
Source: Vail's proposed short-term rental tax draws big-money opposition, led by Airbnb's $30,000 contribution
Maui County, Hawaii
Published: October 23, 2025
Regulation Category: Occupancy
Summary: Maui vacation rental owners are challenging Bill 9, which seeks to convert about 6,000 of 15,000 short-term rentals into long-term housing, passed by the Housing and Land Use committee and awaiting a November council vote. Investors should be aware of arguments that units are unaffordable for long-term residents due to high costs like insurance and HOA fees, with proposals for hotel zones potentially exempting some properties from conversion.
Source: Maui Airbnb owners challenge vacation rental crackdown
San Diego, California
Published: October 23, 2025
Regulation Category: Tax
Summary: San Diego's rules committee approved a proposal for a $5,000 annual tax per bedroom on short-term rentals and non-long-term second homes, potentially affecting 10,644 properties and generating $135 million yearly. Short-term rental investors should track the full council vote, as opponents warn of economic harm and job losses while supporters prioritize local housing needs.
Source: San Diego considers tax on Airbnb and second homes
Bakersfield, California
Published: October 23, 2025
Regulation Category: Zoning
Summary: The Bakersfield Housing and Community Development Committee received an update directing city staff to draft an ordinance addressing short-term rental issues like noise, trash, and parking. Short-term rental investors should prepare for upcoming regulations that could impose new management requirements to mitigate neighborhood impacts once the draft is developed.
Source: City of Bakersfield to begin planning ordinance to manage short-term rentals — including Airbnb, VRBO