Main Road in Southold on Saturday. The town is considering...

Main Road in Southold on Saturday. The town is considering changes that would stiffen penalties for violations of the short-term property rental law and ban separate pool rentals. Credit: Randee Daddona

Southold officials may stiffen penalties for homeowners who rent their properties for less than two weeks and add a provision to town code banning the separate rental of amenities like residential pools, backyards and private sports courts.

The legislation is under consideration as nine cases involving short-term property rental violations landed in the town's court in recent weeks. 

“As these are discovered or reported, they are investigated,” deputy town attorney James Squicciarini said in an interview. “We are certainly acting on all complaints."

The current short-term rental law restricts house rentals to 14 days or more. It doesn't address separate rentals of pools and other amenities.

Under the proposal, fines for renting amenities separately would be between $3,000 and $10,000. The same penalty would be apply to short-term home rental violations — with one exception.

If a home's 14-day lease rate is higher than $10,000, then town officials would penalize any homeowner who rented a home for a shorter term with a fine that matches the lease rate.

For second offenses, town officials would revoke permits and issue fines of up to $20,000. Violators also could face up to 15 days in jail. 

The current penalty for violating the short-term rental law is a $500 fine.

A search of, a site that connects pool owners with renters, shows pools for rent in Southold at hourly rates ranging from $40 to $100.

Supervisor Scott Russell said that under the proposed code, such a use "would be considered a commercial use in a residential zone" and "not permitted."

Russell said the town received “quite a few” complaints about pool rentals last summer. Town officials didn't issue any violations, but two homeowners got warnings and now are in compliance with the current code, according to the supervisor.

The proposed law would require homeowners who rent their properties to display their rental permit number on any advertising, social media listings or websites and also mandate the permit's posting on the property itself.

More than 800 Southold properties are listed on Airbnb.

There are 945 rental permits on Southold's books, according to town building department data, although it's unclear how many of those properties are solely short-term rentals.

The town set a hearing on the proposal for Aug. 29.

At least one other Long Island town is considering a similar crackdown.

In Brookhaven, which has a ban on short-term house rentals that are less than a month, town officials have proposed code changes that would ban property owners from online advertising for those leases and from renting out their pools. The revised code also would impose increased fines for violators.

Brookhaven officials postponed a vote on the measure in May when a hearing drew opposition from residents who said the rentals help them pay property taxes and that most renters don't cause disruptions. 

Separately, in Southold Russell is pushing for leniency in commercially zoned areas of town to allow for rentals of less than 14 days. He also wants to tighten restrictions in residential areas by increasing rental minimums to 30 days. 

He said both those restrictions could help offset the cost of pricey hotels while potentially opening up long-term rental opportunities amid a housing shortage.

“I do think there’s a need for that and I think the commercial zone can address that,” Russell said.

But other Southold town board members said a 30-day rental minimum would price working-class tourists and some families out of the market.

“It pushes this area into a high-end, one-percenter vacation spot,” said Councilmember Sarah Nappa. “If we’re looking at these rentals that are thirty, forty, $50,000 a month, that’s not sustainable for a middle class family.”

With Carl MacGowan

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