Daily Regulatory Notes 07/22/2025
Cities address STRs. Chicago, IL applies tax to STR listings; Orange County, CA reviews enforcement; Largo, FL expresses frustrations over regulation; Ocean City, NJ approves 3% local tax; Londonderry, VT upholds rules. READ MORE.

Chicago is tightening the rules for short-term rentals, aligning them more closely with traditional hotels by extending the state’s Hotel Operators’ Occupation Tax (HOOT) to Airbnb and VRBO listings.
Starting July 1, 2025, hosts will pay a 6% tax on 94% of their gross rental income—on top of already steep local lodging taxes. At the same time, city tourism officials are pushing a plan to increase hotel taxes even further through a proposed Tourism Improvement District, raising the downtown rate to 18.9% for large hotels. While advocates argue this added revenue could fund much-needed tourism promotion to compete with giants like Las Vegas and New York, some hotel operators and event planners are concerned about rising costs driving business away.
As Orange County braces for a potential surge in short-term rentals tied to the 2026 World Cup and 2028 Olympics, a new Grand Jury report is sounding the alarm on outdated and inconsistent STR regulations across the county’s 34 cities.

The report warns that most cities are underprepared for what could be a repeat of the Paris 2024 Olympics, where STR listings doubled and nightly rates skyrocketed. Highlighting wide regulatory disparities and inconsistent enforcement, the report notes that while some cities have STR bans, others allow hundreds of permits—creating enforcement gaps and lost tax revenue.
In Largo’s Del Prado neighborhood, frustrations over short-term rentals have reached a boiling point as Pinellas County quietly pauses its newly required rental certificate process.

The ordinance approved earlier this year, mandates STR hosts obtain a certificate and pass inspection, but the county shut down the application portal to refine the process despite the July 31 deadline. The county confirmed it has received complaints on several of these properties, none of which have filed for compliance.
Ocean City has voted to impose a 3% local tax on short-term rentals booked through Airbnb and similar platforms aiming to capture more revenue from the increasingly popular booking method.
Councilmembers supporting the tax say the modest fee—about $75 on a $2,500 rental—will help offset the city’s rising costs tied to tourism without deterring visitors. But Airbnb raised legal concerns, stating that under state law, the tax should also apply to hotels and motels to ensure fairness. The new tax won’t take effect until 90 days from passage.
In a decisive town vote on Saturday, Londonderry residents chose to uphold stricter short-term rental rules aimed at slowing rental growth and preserving local housing for year-round residents.
The new regulations, originally adopted by the select board earlier this year, survived a repeal effort after residents voted 66–25 to keep them in place. The rules limit new non-owner-occupied short-term rentals to 50 nights per year and require a one-year waiting period before newly purchased homes can be used as short-term rentals unless the owner lives on-site.
In case you missed it:

READ: Daily Regulatory Notes 07/21/2025

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