Southold cracks down on illegal rentals as new restrictions take shape

Southold Town is ramping up enforcement of its rental permit law, pairing new tracking software with a push to bring property owners into compliance as officials weigh broader restrictions on the market.

The crackdown efforts rely on the software program Rentalscape to identify properties operating without a valid rental permit and those advertised as short-term rentals, the town said in an April 23 announcement.

Officials are also advancing new short-term rental legislation that would bar property owners who rent out their properties without a valid rental permit from applying for a short-term rental permit, according to the release.

“This is an essential step in safeguarding the health, safety and quality of life for everyone who lives in or visits Southold,” Supervisor Al Krupski said.

Recent fatal incidents on the East End — including the November 2024 death of Edy Herrera in Mattituck — underscore the need for regular inspections and compliance with fire and safety codes, officials said.

It is illegal for someone to live in a dwelling if the property owner does not have a valid rental permit from code enforcement, according to Southold Town Code.

Short-term or transient rentals are prohibited by town code. They are defined as rentals of fewer than 14 consecutive nights and include any property listed on a short-term rental platform.

The town attorney’s office will notify property owners lacking a valid rental permit within the next two weeks, according to the release.

“Recipients are encouraged to respond within 30 days; failure to do so may result in fines and enforcement actions,” the release stated.

Property owners can either apply for a rental permit or cease rental activity and remove the listing from all platforms. Those who believe they are in violation but do not receive notice are advised to contact the town building department at 631-765-1802.