🎯 STRisker: Bulletin - Southold, NY

A Deep Dive into Your Area’s STR Updates — Helping You Navigate the Ever-Changing Rental Landscape.

No More Shortcuts: Southold’s STR Crackdown Gains Momentum

Southold Town is cracking down on short-term rentals and this time, it’s going high-tech.

With the recent rollout of a software tool called Rentalscape, town officials now have real-time visibility into STR activity. The platform tracks when properties are being rented, making it easier for enforcement officers to catch violations of Southold’s long-standing rule: no rentals shorter than 14 days.

“We’re now able to proactively monitor and enforce the law,” said Assistant Town Attorney Ben Johnson. With Rentalscape’s help, officers can time their property visits for when renters are actually present, making citations more effective and court cases more enforceable.

Back in April, the town brought on a part-time code enforcement officer, specifically assigned to work nights and weekends—the peak window for STR activity. Johnson also confirmed that the town plans to send out warning letters soon to known violators, nudging them to comply before more citations roll in.

Currently, 40 cases related to illegal short-term rentals are active in Town Justice Court, and Southold has logged 25 to 30 convictions over the past two years. With Rentalscape in play, that number may climb quickly.

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But Southold isn’t just leaning on penalties. It’s also eyeing reform. Last August, a task force recommended that the town create a permitting system for rentals under 30 days. The proposed plan would allow homeowners renting their primary residence to apply for permits directly, while non-primary property owners would need to enter a lottery system, with a strict cap of 1% of homes per hamlet.

The Town Board expects to start working on these recommendations this fall signaling a potential policy shift from outright bans to more controlled, capped allowances. The aim? Balance the housing needs of full-time residents with the tourism economy that STRs support.

In a collaborative twist, Southold and Greenport Village Board members also met recently and agreed to coordinate their STR policies moving forward. By sharing draft code language, the two jurisdictions hope to create more seamless and enforceable rules across town and village lines.

Bottom line? Southold is stepping up its STR game with a combination of smart software, strategic staffing, and long-term planning. The message is clear: follow the rules, or the town will be watching.

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