Boston councilors on Oct. 30 questioned city enforcement of the short-term rental ordinance, citing examples where residents said listings skirted rules through exemptions, platform workarounds and documentation that ISD said it must accept. The hearing before the Boston City Council Committee on Housing and Community Development opened with sponsor Councilor Gabriela Coletta Zapata saying the ordinance's intent was to "protect our city's housing stock, safeguard neighborhood stability, and ensure that our homes are not treated like hotels by absentee investors."

City Inspectional Services officials told councilors they use a combination of the Airbnb city portal, a vendor "scrubbing" tool (Host Compliance) and on-the-ground inspections to identify unregistered or noncompliant listings, but that operational and legal limits curb enforcement. Director Regina Hanson said the ordinance "has been credited with recently with reducing listings by up to 56%, but challenges' should remain," and acknowledged gaps in tracing hospital and corporate exemptions and in the timeline for taking down listings.

ISD described standard proof for a primary residence (utility bill, voter registration, state ID, deed or lease) and said owners sometimes supply documentation that meets those requirements even when neighbors report repeated short stays. "Some of the things that are provided to our office in terms of complaints such as the presence of suitcases [or] behavior of guests'aren't necessarily sufficient evidence" to rebut a submitted contract, ISD staff warned.

Councilors and ISD staff detailed operational constraints: a vendor scrubbing service returns documented stays on a monthly cadence; Airbnb allows a multi-week correction window after the city requests a block on a listing; and ISD lacked hearing officers for roughly four years after the pandemic, a gap that slowed ticket adjudication. Regina Hanson said she personally reviewed hundreds of applications this year ("903 applications already this year") and that renewal and coaching work can take substantial staff time.

Councilors pressed for tighter remedies and better technical integration. Members described tactics they said hosts and platforms use to avoid short-term rules, including moving listings to a 29-night minimum or relying on "hospital stay" and corporate contracts. Councilor Sharon Durkin noted a platform heat map that appeared concentrated in her District 8 and said she had met with Airbnb about compliance.

Public-safety and quality-of-life concerns drew comment from Boston Police Deputy Superintendent John Brown, who described the department's response to noise and party calls, tracking methods (service dispositions and incident reports) and escalation to detectives or community service offices when needed.

Speakers representing neighborhood groups urged policy changes. Ford Cavalieri of the Alliance of Downtown Civic Organizations said litigation and federal law (Section 230) complicate takedowns and that independent checks show many listings remain unregistered; he recommended adding licensing and inspection layers for exempt categories and tightening zoning and fire-safety oversight for properties operating like hotels.

ISD officials and councilors agreed to pursue a working session to review ordinance language, technology integration with platforms and possible budget or staffing changes. No formal legislative action or vote was taken at the hearing.