The court order requests argue the tenants acted in a "clandestine and fraudulent manner" and "developed a scheme to avoid being unmasked."

In early June, “Catherine” made her way to a downtown Montreal condo complex and waited for the man who was supposed to meet her there. She had rented out a unit in the building on Airbnb and was now looking to pick up the keys.

A few minutes before arriving, the man called to tell her she needed to head to a neighbouring building instead: because of a problem with the listing, he said, the address she saw online wasn’t the right one.

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When they finally met up, the man quickly explained how to use the key card to enter the building, showed her to the elevator, and told her to leave the keys on the kitchen table at the end of her stay.

As she entered the unit — advertised online as “Downtown condo upscale 1” — it seemed more like a hotel room than someone’s home: it had just been cleaned, and the pantry, fridge, freezer, closets and cupboards were all mostly empty. The kitchen held only a few basic cooking items. A tourism magazine was on display in the living room.

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“Catherine” had rented the unit online for two nights for $900. But unbeknownst to the person lending her the keys, she was not someone looking for a place to stay while visiting the city, but rather an undercover GardaWorld investigator hired by the building’s management. Another investigator sat in a car parked outside, filming their transaction.

The condo complex in question, the Roccabella towers on René-Lévesque Blvd., prohibits short term rentals through its co-owners declaration and building rules.

After repeated attempts to deal with the issue through more traditional means, management hired the investigators in an attempt to catch people in the act.

Using the evidence collected through the investigation, the complex’s co-owners syndicate is now seeking court orders to get them to cease renting out the units online. They’re also seeking damages for other owners in the building.

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“There have been a number of people who didn’t understand the rules, hadn’t seen them or weren’t aware of them. We’ve always handled those cases,” said Serge Labelle of MC Finance, the company that manages the syndicate.

“But in this case, we had a situation where we knew it was recurring and we were maybe dealing with the beginning of a network that would do it on a larger scale,” he said. “They were well aware of the rules but still did it with impunity.”

The syndicate has filed injunction requests targeting three owners and two tenants (who signed one-year leases with condo owners) in connection with two units management believes have been rented out on Airbnb and similar online platforms.

For one of the tenants, the court documents allege, management first noticed he listed the unit on Airbnb under the username “Mtl Luxury” a few days after signing a one-year lease in June 2018. The rental page advertised the building’s shared pool, jacuzzi and gym as features that came with the unit.

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Management informed the tenant he was facing a $1,000 fine if he didn’t remove the listing, but when confronted about it, he insisted he wasn’t renting out the unit. They agreed to drop the fine.

When they found out he rented it again in October — they were tipped off when a stranger asked building staff where he should leave the keys on his way out — they again issued him a fine: $2,000 this time given the repeat offence.

The tenant refused to pay it, the documents say, and responded by telling management he wasn’t renting out the unit but had welcomed members of his church who came from Halifax for Thanksgiving weekend.

In a meeting soon after, he swore he would never rent out the apartment, and they again agreed to drop the fine. But his commitment, the documents state, “would turn out to be nothing but a tissue of lies.”

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Come April, complaints started accumulating about a continuous flow of people coming and going from the building, all carrying small suitcases.

An internal investigation in which it had an employee rent out the unit on Airbnb discovered the same tenant was still using the platform, leading to the GardaWorld investigation.

“We decided we needed to build a case, and that’s how we found out our suspicions were founded,” Labelle explained.

The court requests argue the tenants acted in a “clandestine and fraudulent manner” and “developed a scheme to avoid being unmasked.”

To go undetected, the documents say, they had someone else hand over the keys to renters, didn’t list the real address on Airbnb, had people meet nearby instead of at the complex itself and asked them to leave the keys inside the unit to not raise suspicions with reception.

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The syndicate is also seeking damages for other owners who’ve been affected by the “repeated presence” of strangers in the building.

“There have been complaints about the noise, people not knowing how to use the facilities, trash being left in hallways, the list goes on and on,” said Carmine Mangiante, director of building operations for the complex.

“We’re not the only building that has this problem,” Mangiante added, “but we’re trying to put a stop to it as much as possible.”

In June, the provincial government announced it will be introducing tougher regulations for online short-term rental platforms such as Airbnb. The regulations are expected to come into effect in the fall.

In Montreal, some boroughs have restricted short-term rentals in certain areas, but advocates continue to call for stricter rules , arguing the issue is driving up rent prices and eating away at the housing supply in central neighbourhoods.

Labelle said he’s encouraged by the steps the government is taking but, for him, bringing the matter to court is about sending a clear message that it goes against the building’s rules.

“It’s for the benefit of all owners,” he said. “It’s a plague, and in a case like this one, it’s completely unacceptable.”