Short-term rental official corrects counts and flags enforcement gaps
Summary
Jay Williams, the town official overseeing short-term rentals and zoning, told the board the town has 338 permitted short-term rentals (permitted) and about 478 active accounts in the tracking system, cited duplicate listings across platforms, and said the third‑party monitoring software underperformed, prompting a contract cost reduction and renewed review of enforcement options.
Jay Williams, introduced by the board as the official responsible for short-term rentals and zoning, briefed the Town of Web on the program's third year under the local law. Williams said the accurate permitted count is 338 and that the tracking system currently shows 478 active accounts — a discrepancy he attributed to duplicate listings on multiple sites and listings that remain on the town's radar while owners resolve inspection or repair issues.
Williams described the town's experience with a third-party software vendor intended to identify listings and manage renewals: the vendor initially proposed a $25,000-per-year package that fell short of expectations; the town negotiated the contract down to $10,000 per year as renewals approached. Williams said the town is performing renewal inspections and chasing noncompliant listings; enforcement options under review include issuing tickets or pursuing court actions. He said the town is gradually finding listings through Facebook and smaller local sites in addition to major platforms.
Board members asked about caps in neighborhood zones and whether accurate counts would affect long-term housing availability; Williams and board members agreed better enforcement and clearer data are needed before additional regulatory steps are taken.
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