TripAdvisor-owned vacation rental site FlipKey is dipping its toes into the New York market, but it may get them bit off before it gets a firm footing.

[Updated with quote from FlipKey, below]

Unlike the apartment share site Airbnb, which specializes in urban rentals, FlipKey has traditionally kept to vacation and second-home markets like Orlando, where local laws don’t restrict activity to such an extent. Despite the ubiquity of illegal sublets available on sites like Airbnb, New York City bans almost all cases of short-term rentals for less than 30 days.

According to the management of New York City’s largest rental complex, Peter Cooper Village/Stuyvesant Town, FlipKey is targeting residents with letters encouraging them to list their units on the vacation rental site.

In response to the FlipKey letter, management sent out an email today and posted a message on its Facebook page to warn residents of the ramifications they could face if caught subletting their units as short-term rentals:

Dear Residents,

We have recently been made aware of an advertisement sent to all residents by FlipKey encouraging you to rent your apartments while you are out of town.

Please remember that apartment rentals for fewer than 30 days are prohibited under NYC law and use of this service is a violation of your lease and your tenancy. Furthermore, short term rentals such as these are harmful to the PCVST community and negatively impact your neighbors.

Residents who are found to illegally rent their apartments in this manner are subject to penalties including lease termination and eviction.

PCVST is also exploring legal options against the company to ensure that FlipKey does not operate in our community.

Sublet requests and roommate changes are allowable but are subject to the rules in your lease and require Management’s prior approval.

In addition to the threat of eviction, fines from the city run into five figures, depending on the number of violations.

In response to questions from Skift about this particular matter, FlipKey’s COO and co-founder Jeremiah Gall responded, “FlipKey works with verified short term rental owners and suppliers who certify to FlipKey that they comply with local laws and regulations. When we are notified regarding non-compliance with these local rules and regulations, we will investigate appropriately.”

In February, a coalition of vacation rental sites led by HomeAway launched the Short Term Rental Advocacy Center. Its stated goal is protect the rights of providers, who seek to rent properties for 30 days or less, from restrictive local laws. The group says it has chapters in about 10 cities.

Photo Credit: View of PCVST from across the East River. Dan DeLuca / Flickr