The Great Airbnb Crackdown

Last year, a massive blaze consumed several illegal Airbnb units in Montreal and killed seven people. The tragedy shone a harsh light on the Wild West of Airbnb in Canadian cities—and the battle to regulate it has just begun.
CAITLIN WALSH MILLER
Fire 5 alarms 135 rue du PortOld Montreal

April 4, 2024

As soon as Nathan Sears checked into his Airbnb in March of 2023, he knew something felt wrong. The door to his unit was so flimsy he thought he could kick it down. The building’s front entrance was unlocked, open to anyone who might wander in. He called his wife, Araceli, and gave her a video tour—he didn’t want to leave any valuables inside, he said. It didn’t feel safe.

But the Airbnb was in a prime location, on the second floor of a beautiful, three-storey limestone heritage building in Old Montreal, at 135 rue du Port. It was just a 20-minute walk from the venue for the conference that Sears—a young academic in the field of existential risk—was in town to attend. And it was a steal, at $58 a night. Sears didn’t know that, of its 14 units, nine were being used as short-term rentals, all of them illegally operated. 

Nor, in all likelihood, did An Wu, a 31-year-old neuroscientist with the University of California who was also in Montreal for a conference. She was staying on the third floor, as were Saniya Khan, from Michigan, and Dania Zafar, from Toronto, childhood friends in town for a one-day trip. Alina Kuzmina and Simone Mereu—a couple in their twenties from Cornwall, Ontario, who were visiting for a concert—were in the basement. It was down there, just after 5:30 a.m. on March 16, that they were woken by an explosion. Smoke curled under their door and flames crackled in the hallway. The pair broke a window and crawled onto the street. Once outside, Kuzmina turned toward the building in time to see someone jump from an upper storey.

That was probably Eduardo Chairez or Pedro Pozos. The two young men, visiting from Indiana, were staying with two other friends in a unit on the second floor. They had woken to smoke so dense they couldn’t see. One member of their group groped along a wall until he reached a window. He smashed it, slicing an artery in his arm, and the four crawled out onto a ledge. Chairez and Pozos jumped, sustaining minor injuries. The other two were rescued by firefighters, minutes before flames engulfed the second storey.

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Somewhere behind the flames were Charlie Lacroix, from the Montreal suburb of Terrebonne, and Walid Belkahla, from Laval. The 18-year-old friends had booked a windowless room deep inside the building. They called 911 twice. “Come get us,” Lacroix told the dispatcher. “We can’t get out.”

Patrick Brasseur was getting ready for work when he heard the explosion that woke Kuzmina. The 54-year-old construction worker was one of the building’s few long-term tenants. He’d lived at the rue du Port building for more than three decades, and so was among the few who knew about its long history of fire safety violations. There were no fire doors and insufficient alarms. The third-floor fire escape was only accessible via a vacant, locked apartment. The door to the staircase nearest to him was padlocked shut. Brasseur had been so concerned about fire that he’d made his own escape rope and kept it tied to a radiator by his window—though he couldn’t use it the morning of the blaze because he couldn’t find it through the suffocating smoke.

It took 130 firefighters a full day to tame the fire, which gutted the building. Nathan Sears’ parents, Randy and Beth, were in Spain when they found out their son was missing. Two days later they were in Montreal, along with other relatives. Together, the families spent six, seven, eight hours a day at the site, in frigid March temperatures, watching drones photograph the wreckage from the air as police officers and firefighters dismantled the unstable structure.

Altogether, seven people died that night, including Wu, Khan, Zafar, Belkahla, Lacroix and Sears. Six of them were staying in illegal Airbnb units. It took 11 days for searchers to recover their remains. The body of 76-year-old Camille Maheux, a renowned photographer and another long-term tenant, was the first to be identified. Nine days later, search dogs located Sears’ body in the basement—he likely slid off his bed and fell through the collapsing structure. 

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Nathan Sears, pictured here with his sister, Brittany, was among the seven people who died in the fire.

The tragedy stunned the city. Old Montreal is a small neighbourhood, less than one square kilometre. Its cobblestone streets and chic boutiques are popular with tourists—so popular that, a few years ago, locals began to feel they were being squeezed out by landlords turning apartments into short-term rentals, or STRs, listed on platforms like Airbnb. In 2018, the borough of Ville-Marie, which includes Old Montreal, banned most commercial STRs. Hosts who rented out their own homes were in the clear, but multiple-property owners were banned from operating full-time tourist rentals in investment properties. That was on top of provincial legislation introduced two years earlier, which required STR hosts to license their units, paying a one-time fee of $250 and a small hotel tax. Yet at the time of the fire, there were over 3,500 Airbnbs in Ville-Marie, according to the data-tracking site Inside Airbnb, which is run by a community activist in New York. More than 60 per cent were hosted by people who had multiple listings, suggesting they were commercial operations. Only 11 per cent were licensed.

In the aftermath of the tragedy, Emile Benamor, the building’s owner, disavowed involvement with the Airbnbs. Instead, he placed blame on a tenant, Tariq Hasan, to whom he leased at least seven apartments in the building. (Hasan declined an interview request made through his lawyer; Benamor’s lawyer did not respond to repeated calls and emails.) Mayor Valérie Plante, in turn, condemned the units as illegal, but also said it was the province that was responsible for inspecting provincial licensing; a spokesperson for Revenu Québec, the agency in charge of those inspections, said that its mandate was not to enforce municipal regulations. Plante also accused Airbnb itself of washing its hands of responsibility; the company issued a statement, saying, “Our thoughts remain with those impacted by this tragedy.” 

Randy Sears first considered legal action during the eight days that he stood vigil in the winter cold, waiting for his son’s body to be unearthed. He knew Nathan was a vigorous young man—if there was an escape, he’d have found it. He reached out to Annette Lefebvre, a personal injury lawyer with over three decades of experience. Two weeks after the fire, he spoke to Lefebvre and her associate Melissa Lonn by phone. A day after that, they filed a $22-million lawsuit against Benamor, Hasan and Airbnb, alleging that the rental units—owned by Benamor, operated by Hasan and advertised and made available for booking on Airbnb—were unsafe and illegal. 

More than 15 years after its debut, Airbnb has transformed the way we travel, allowing people to experience new destinations and unique accommodations. In the early years, it was cheaper than hotels, and it became the default option for plenty of millennials, budget travellers, and families and groups looking for space to spread out. But as investor-owned Airbnbs spread to meet demand, they also transformed our cities. Critics blame Airbnb for driving rents up and vacancy rates down and for hollowing out residential buildings, especially in tourist areas like Old Montreal. And like other big tech disruptors that rose alongside it, the company has a long history of outmaneuvering regulation. In Montreal, in particular, Airbnb faced some of the earliest STR regulations in Canada, only to operate more or less in defiance of them for years.

Lefebvre and Sears’ suit could change that. Despite years of controversy—and assaults and deaths—the company has never been held liable in court for injuries sustained in a rental. Instead, it’s spent millions over the years on out-of-court settlements. The suit could be precedent-setting in another way as well. Last October, Lefebvre and Lonn added the city of Montreal as a defendant, on the grounds that it failed to enforce its own rules regulating Airbnb. A victory could be a piercing wake-up call for other cities, coming just as a new wave of crackdowns begins to take shape in communities around the world—and creating an existential risk to Airbnb as we know it.

Airbnb’s origin story is the stuff of Silicon Valley lore. In 2007, Brian Chesky and Joe Gebbia were design-school grads struggling to make rent in San Francisco. A huge design conference was coming to town, and hotels were booked solid. The entrepreneurial duo bought some air mattresses and threw together a quickie website where conference-goers could rent space on their floor for $80 a night. The pair hosted three guests for a few days, cooking breakfast and playing tour guide. Thus was born AirBed & Breakfast.

In 2008, Chris Sacca, a venture capitalist who had backed Uber and Twitter, passed on funding the startup. It was too dangerous, he told them: “Somebody’s going to get raped or murdered, and the blood is gonna be on your hands.” Sacca was an outlier. Three years and one important name change later, Airbnb was a Silicon Valley unicorn—a startup valued at more than $1 billion.

That year, a San Francisco host’s house was ransacked by guests. She claimed that after she wrote a blog post about the incident, one of Airbnb’s co-founders asked her to remove it, as it might have jeopardized an upcoming round of funding. The move backfired when the host blogged about that interaction. The whole thing got its own Twitter hashtag, #ransackgate. In response, Airbnb instituted a $50,000 host guarantee to cover damage caused by guests, and established a dedicated trust and safety team.

But the incidents didn’t end there. In 2011, a host raped two women in Barcelona. In 2013, a Canadian woman died of carbon monoxide poisoning in a Taipei Airbnb. In 2015, another woman was raped, this time in New York City by a man who had a duplicate set of keys for her rental. Another woman was assaulted by a host in L.A. in 2017; the next year, an American woman was murdered in Costa Rica by a security guard at the complex where she was staying. When I asked Airbnb about these incidents, the company responded that it could not comment on specific cases, but added that fewer than 1 in 1,000 stays results in a safety report from a host or guest. Criminal incidents are rarer still.

Even those horror stories that grabbed headlines have done little to slow the company’s extraordinary growth. By 2017 there were approximately 70,000 hosts in Canada alone; two years later, there were more than six million listings worldwide. That was more, the company bragged, than the number of rooms owned by the top six global hotel chains combined.

By then, many cities had grown wise to the fact that Airbnb hosts were turning residential buildings into de facto hotels. The first wave of municipal regulations targeting the company, in the mid-2010s, mostly aimed at getting it to collect hotel taxes. In response, Airbnb got litigious. It took Florida’s Palm Beach County to court three times over five years to avoid paying. It sued Vienna, Boston and Miami. Elsewhere—in Tennessee, in Texas—it lobbied politicians and helped draft bills that prohibited banning STRs. Whenever it faced regulation, Airbnb made a similar argument: it allowed regular people to rent out their homes for extra money, providing value to users and hosts. And that was true. For some people, renting out a basement or a spare room helped pay the mortgage or the rent in Canada’s increasingly expensive housing markets.

But those hosts eventually took a backseat to a different kind of operator. According to David Wachsmuth, an associate professor of urban planning at McGill University, “full-time” short-term rentals—booked for 60 days or more per year, and unlikely to be occupied by long-term tenants—increased by more than 50 per cent in Canada’s three largest cities between 2015 and 2016 alone. By that time, commercial property managers, some of whom owned hundreds of units, brought in a third of the company’s revenue, despite accounting for just eight per cent of listings. According to Wachsmuth’s research on the company’s impact on housing markets, Airbnb took 13,700 homes off the market in Montreal, Toronto and Vancouver in 2017.

Fairbnb Canada is a non-profit that advocates for stricter STR rules. According to its data, in 2019, commercial operators accounted for 42 per cent of Toronto hosts, and nearly three-quarters of Airbnb’s revenue in that city. That same year, Wachsmuth estimated commercial STRs had taken 740 units out of Halifax’s housing market. He found that if all of them were to become long-term rentals, the city’s 1.6 per cent vacancy rate, blamed for skyrocketing local rents, would have climbed to a healthy 2.8 per cent.

In a decade, Airbnb has created a new class of landlord-entrepreneur, propelled by irresistible financial incentives: charging $100, $200, $300 a night, especially in popular neighbourhoods and tourist areas, is a lot more profitable than renting to one tenant for $2,000 a month. According to a recent study by Desjardins on the impact of STRs on housing, the average annual income for a short-term rental in Montreal is today $50,000, twice that of a traditional apartment. And as the financial opportunities have grown, so have the incentives to sidestep the growing but weakly enforced rules intended to protect housing stock—and to ensure the safety of tenants, long- or short-term.

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Emile Benamor owned the building at 135 rue du Port, along with nearly two dozen other properties in Montreal. His real estate portfolio is likely worth more than $25 million. (Photo by Edouard Plante-Frechette via La Presse)

Emile Benamor, the owner of 135 rue du Port, spent the first few decades of his career working as a lawyer in the youth division of the Court of Quebec. He had a reputation for handling a large number of files. According to an investigation by Quebec’s La Presse, one lawyer filed a complaint to the Quebec bar against him, suggesting he couldn’t possibly handle so many cases. In 2013, the convictions of two of his teenaged clients were overturned after the Court of Appeal found that Benamor had pressured them into pleading guilty. By then, he’d branched out into traffic violations and ran a payday loan company called Loans SOS. In 2021, he was found guilty of tax evasion after failing to declare $470,000 in income from a telemarketing scam. The Quebec bar limited his right to practise, but he’d mostly stopped working as a lawyer anyway, shifting his focus instead to his real estate portfolio, which today comprises at least 15 buildings and may be worth more than $25 million, based on municipal property assessments. That list includes 135 rue du Port, which Benamor bought in 2009 for about $1.6 million. 

Soon after his purchase, Benamor allegedly began a campaign of harassment, concocting reasons to evict tenants and relist the units at higher rents. Catherine Joyal lived in the building with her boyfriend, Piotr Torbicki, from 2009 to 2012. She says that Benamor repeatedly barged into their basement unit early in the morning, sometimes accompanied by six or seven men. He would yell that they had to leave, one time even sitting on the edge of the bed with Joyal, who was only partly clothed under the covers.

Joyal also suspects Benamor stole mail sent to her and Torbicki by the provincial housing tribunal. Benamor was trying to get them evicted and, after they missed a hearing, the tribunal ruled in his favour. The couple appealed the decision, explaining that they never received the notice of appearance, and it was reversed. Joyal told the judge she thought her mail was being stolen; the next day, she says, a pile of opened letters from the tribunal appeared on her doorstep.

In 2016, Quebec passed its first STR rule, requiring owners to obtain a certificate from the province’s Ministry of Tourism and pay a small tax. That didn’t dissuade Benamor from getting into Airbnbs. Investigative journalism outlet Ricochet reported last year that he signed a lease in 2017 with a tenant in another building, specifying that “the landlord allows short-term sublets and Airbnb rentals.” Those units were unlicensed, despite Quebec’s new rule. (A year later, less than five per cent of Montreal’s roughly 12,500 Airbnb listings had licences. Across the whole province, only 18 violations were identified; zero fines were issued.) In 2018, some boroughs, including Ville-Marie, introduced their own bylaws, restricting commercial STRs to limited stretches of major streets—none of which were in Old Montreal. This made the units in Benamor’s building illegal twice over, provincially and locally. By 2019, five of the 10 neighbourhoods in Canada with the highest concentration of Airbnb listings were in Montreal. 

The city was far from alone in the struggle to translate bylaws into enforcement. In communities worldwide, Airbnb was sidestepping regulation. In 2015, a report by the state’s attorney found that nearly three-quarters of New York City’s Airbnb units were illegal. In response, the company said it would voluntarily share numbers with the city. Days before it was due to do so, it purged 1,000 listings likely owned by investors, skewing the picture in its favour. In Barcelona, in 2018, the city government struck a data-sharing agreement that required Airbnb to provide more information about hosts’ identities and locations, but up to 70 per cent of the data Airbnb supplied was incorrect or incomplete. That same year, Vancouver passed a bylaw requiring listings to include a licence number. Airbnb removed non-compliant listings, but it also allowed hosts to use a loophole: properties were listed as being in nearby suburbs, though they were actually in the city of Vancouver itself, and could be found on the platform’s map of the city. 

Tariq Hasan, the tenant who would later rent multiple units at 135 rue du Port, hosted his first STR in April of 2019, in a high-rise building near downtown. According to an interview he gave that year on a podcast for STR investors unearthed by Ricochet, he was soon managing five units across three locations, making triple what he did at his day job as a software engineer. He was able to scale because of the partnership he had with a landlord: “I met a real estate investor who didn’t mind people taking his apartments and putting them up for short-term rental.” Eventually, Hasan was running Airbnbs for Benamor at 135 rue du Port and at least two other Benamor buildings.

At the same time, the Montreal fire department was compiling a file several inches thick on 135 rue du Port. Starting in 2009, fire inspectors flagged a string of recurring violations, including non-functional fire alarms, a lack of smoke detectors, a dead-end hallway and problems with escape routes and evacuation plans. Benamor expanded a third-floor unit into the hallway, blocking access to the emergency staircase, in violation of Quebec’s construction code, yet the plans were approved by the city. For over a decade, notices of infraction were sent, mostly by one city inspector, Geneviève Tremblay. Few violations were addressed, and there were barely any consequences for Benamor. He paid a $714 fine in 2010 for problems related to firewalls, which slow the spread of flames. Charges related to the fire alarm system and evacuation routes were issued in 2013, but later withdrawn. In 2014 and 2018, Geneviève Tremblay requested the file be forwarded for judicial proceedings. Both requests were refused; the reason for the 2018 refusal was simply “moratorium.” That was a reference to a years-long suspension on enforcing safety standards, due in part to lack of staff training, a lack of clarity around compliance and other systemic turmoil within the department.

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For more than a decade, fire inspectors flagged multiple violations at 135 rue du Port—including missing smoke detectors, a dead-end hallway and blocked escape routes—few of which were ever addressed.

Even as the safety problems mounted, 135 rue du Port kept pulling in money, as more units were converted to STRs. Inside Airbnb estimates revenue from individual listings, and though Airbnb itself disputes its data, it doesn’t provide its own, and the site has become a widely used resource for academics, journalists and local governments. According to its estimates, the rue du Port basement unit that Alina Kuzmina and her husband scrambled out of the morning of the Old Montreal fire had, in the year prior, brought in $16,000. The second-storey unit that the Indiana students leapt from generated $19,000. The windowless room that trapped Charlie Lacroix and Walid Belkahla earned more than $13,000. The unit Nathan Sears died in was less valuable, only earning about $2,500. 

Inside Airbnb has information on eight of the building’s nine STRs. Their total revenue in 2022 was nearly $175,000. If all 14 units in the building had been rented as Airbnbs, they could plausibly have bought in more than $300,000 altogether. On the regular market, the units would have had to rent for an average of $1,800 per month to accomplish that—far more than ones in the building were commanding. Patrick Brasseur’s rent, for example, was only $750 a month.

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76-year-old Camille Maheux, a renowned photographer and a long-term tenant at 135 rue du Port, was the first to be identified among the dead.
An Wu
Neuroscientist An Wu, like Nathan Sears, was in Montreal for a conference. She was among the seven people who died the night of the fire.

Annette Lefebvre, Randy Sears’ lawyer, has seen a lot of death and dying in her career. In order to pay for law school, she worked for years as a nurse, including in Toronto and California. She then studied law at McGill and was called to the bar in 1991. In more than 30 years of practice, she’s exclusively represented plaintiffs against doctors and hospitals, insurance companies, landlords and property owners. But she says the Airbnb case is different. “It’s given me nightmares,” she says. “To know that you can’t escape the smoke and you’re going to be burned to death? I can’t think of a more horrific way to die.” 

After Lefebvre and her associate Melissa Lonn spoke with Randy Sears, they correctly assumed that since most of the fire’s victims had been in Airbnbs, their families would be scattered around the world. They proposed a class-action lawsuit—something they could get on the books fast, filling in the blanks later. They already had a good lead plaintiff in Randy Sears himself: a devastated but impassioned and articulate father. 

Airbnb has taken many steps over the years to insulate itself from legal repercussions. In the U.S., by far its largest market, a 30,000-word user agreement binds hosts and guests to confidential arbitration to resolve disputes and requires them to waive the right to class actions or jury trials. Canadian users aren’t bound by these clauses, thanks to consumer protection laws prohibiting them. But in Canada and globally, the company has always sought to settle away from the public eye. And it has the budget to do so: according to a 2021 investigation by Bloomberg Businessweek, the company spends an average of $50 million annually on payouts to hosts and guests, including legal settlements. Airbnb reportedly offered the family of the Canadian who died from carbon monoxide poisoning in Taipei $2 million to resolve the matter. The woman who was raped in New York in 2015 reportedly received $7 million. The family of Carla Stefaniak, the woman murdered in Costa Rica in 2018, settled for an undisclosed amount. In 2019, five people died when a gunman opened fire at an out-of-control party in California. Airbnb agreed to pay funeral costs for the victims, but then began haggling. “They don’t care anymore, because the news cycle has moved on,” a lawyer for one of the victims’ families told Bloomberg.

After Lefebvre and Lonn filed the class action, news about the suit appeared online—and their phones began to ring. Survivors and relatives of the deceased reached out, telling their stories. That’s when a pattern emerged: windows that were glued shut. Doors too hot to touch. Hallways filled with smoke. No fire alarms. No escape. “It was the same story, over and over,” says Lonn. “No one who survived walked out the front door.”

It was becoming clearer to Lefebvre and Lonn that the role of the city itself, after more than a decade of allegedly negligent inspections and enforcement, was crucial to the case. They refiled the suit last October, as a joint action on behalf of 47 plaintiffs: survivors, the dead and relatives. Last August, Montreal police announced that the fire was being classified as arson. Traces of gasoline were found in a basement stairwell and in October, La Presse reported that a suspect, a 63-year-old career criminal named Denis Bégin, had already been in custody for months on unrelated charges. But for the moment, Lefebvre says, the source of the fire is incidental to the lawsuit: “The building was a fire trap, and the city turned a blind eye to its own fire safety rules and short-term rental regulations.”

Lefebvre and Lonn are also adamant that Airbnb should have known about the building’s problems. A guest they spoke to who stayed there in 2022 complained to the company that her unit’s windows were glued shut; a customer representative responded and said that her concerns were reported, and the case was closed. In any case, the units were illegal. “If Airbnb had been doing its due diligence,” says Sears, “Nathan wouldn’t have found this building on the internet. Nathan and the others would be alive today.”

As it so often has, Airbnb expressed an interest in settling out of court. The plaintiffs were willing to consider it. By the time this is published, the plaintiffs may have received the offer and decided whether or not to accept it. Regardless, the action against Benamor, Hasan and the city will proceed.

In the past few years, the housing crisis has spread far from our biggest cities, becoming a nationwide emergency. As a result, communities are feeling heightened urgency to get STRs back onto the long-term market. Airbnb isn’t the primary driver of Canada’s housing undersupply, of course—but, says researcher David Wachsmuth, unlocking the units currently used as commercial STRs should be low-hanging fruit. The federal government estimated in 2020 that in Montreal, Toronto and Vancouver alone, nearly 19,000 properties were being used as full-time STRs, a number that has almost surely increased since. Wachsmuth puts the current figure nationally at about 50,000, though that is a very rough estimate. Meanwhile, in 2023, Canada’s national rental vacancy rate fell to 1.5 per cent, the lowest since tracking of the metric began in 1988. So cities have begun rolling out bigger guns—or rather, bigger bylaws.

In 2021, Toronto passed a requirement that Airbnbs can only be rented out of a host’s primary residence, which would theoretically end commercial STRs. The results have been mixed. Inside Airbnb still shows nearly 6,000 Toronto STRs on Airbnb, 40 per cent of which are listed by hosts with multiple properties. Reporting by the Toronto Star this January found that some property management companies have encouraged clients to change the address on their driver’s licence to that of their investment property, to make it appear as if they’re renting out their own home. “We have families that have four or five units, and every member of their family is, on paper, living in a different apartment,” said one sales representative for a company called GlobalStay, a property management outfit that specializes in STRs. 

Ottawa and London instituted their own rules in 2022, and Hamilton, Charlottetown and Halifax did last year—though, like Montreal, Halifax still permits commercial STRs on certain mixed-use main streets. Regulations are even trickling into rural communities. The township of Muskoka Lakes, in Ontario’s cottage country, is considering a licensing system for STRs to clamp down on rambunctious guests, restrict rentals to a minimum of seven days and limit how frequently a property can be listed. Muskoka Lakes mayor Peter Kelley told CBC this February that some people are “literally running unsupervised commercial resort hotels.”

The strongest set of rules yet will start to take effect this May in British Columbia, where the provincial government estimates 16,000 units are potentially being used as STRs. There, a sweeping set of measures called the Short-Term Rentals Accommodation Act will restrict STRs to a host’s residence or a secondary suite on the property. A handful of small towns and tourist hot spots are exempt. There will be higher fines for violators, including platforms like Airbnb, and an obligation for hosts to publicly list licence numbers.

Andy Yan, an associate professor in urban studies at Vancouver’s Simon Fraser University, says the key aspect will be enforcement: “Will platforms like Airbnb accept the legislation, or become an obstacle to it?” For the time being, Yan anticipates the latter. The financial incentive to maintain the status quo is simply too great. In B.C., for example, the top 10 per cent of hosts—the biggest commercial operators—earned more than $65 million last June alone, more than half the platform’s revenue in the province that month. 

Even following last year’s fire, Montreal’s STR operators didn’t fall into mass compliance. In the immediate aftermath, Airbnb disabled listings that didn’t include a registration number. More than 7,000 disappeared. But of the 2,800 that remained, more than 2,200 were using licence numbers shared with another listing. Last September, Quebec tightened its rules further, taking direct aim at the platforms with fines of up to $100,000 per illegal listing. Still, 75 per cent of short-term listings active in December were operated by hosts with multiple listings, and nearly 1,900 used a licence number also used by a different unit, according to data from Inside Airbnb. Nathan Rotman, Airbnb’s regional policy director for Canada, told me that the company has verified that every listing is in compliance with provincial law, but a spokesperson for the city of Montreal said this only means that the company verified there was a number in the registration field—not that it’s unique to that listing.

Montreal is attempting to beef up enforcement. Last August, the city launched a new four-person squad to assess properties and hand out fines of up to $2,000 for individuals. They can also bump cases up to Revenu Québec. But it’s a reactive system, driven by complaints. When the squad first launched, it got dozens of tips monthly. Now it’s only three or four. Without specific complaints, the squad conducts a digital scavenger hunt, looking at listing photos and descriptions to determine which may not be in compliance. There are higher-tech options, however. London, Ontario, uses Host Compliance: AI-enabled software that identifies addresses, and estimates occupancy and rental revenue. In 2023, it helped sniff out 123 unregistered listings. Burnaby, B.C., uses it too, and estimates 15 to 20 per cent of its listings are breaking the rules.

No city in Canada has yet gone as far as New York, which last September essentially banned most STRs, restricting all rentals to 30 days or more unless the host is actually present. This model hasn’t been the mainstay of Airbnb’s business for years, since not long after Chesky and Gabbia were cooking breakfast for Airbnb’s first guests in their San Francisco apartment. 

The New York ban has been a success in reducing short-term rentals. As of this February, there were only 4,500 STRs in the city’s five boroughs, compared to 22,000 before the ban. But many of those that disappeared became so-called “medium-term rentals,” listed for 30 days or more. In an interview last fall with the Financial Times, CEO Brian Chesky indicated that the company wants to push into longer-term housing, serving business travellers, families relocating, people in need of somewhere to stay during disruptive home renovations, and so on. This has already created worries about a shadow rental market—it’s unclear what tenant protections apply to guests in these situations. In 2022, a Swiss couple and their children planned a nearly year-long relocation to Toronto for work. Unable to find accommodation due to the city’s housing crunch and their lack of Canadian credit, they booked an extended stay at an Airbnb. It was cancelled halfway through, and Ontario’s Landlord and Tenant Board upheld the eviction, ruling that the family didn’t qualify as tenants and weren’t entitled to the protections that come with that designation, because they booked on an STR platform. There are also concerns that if STRs are pushed off of established apps like Airbnb, they’ll make their way to other corners of the internet, where there are fewer protections and regulations for hosts and guests. In New York this past fall and winter, some STRs began popping up elsewhere—on WhatsApp and Signal groups, and on sites like Craigslist and Facebook Marketplace. 

Andy Yan at Simon Fraser believes that as the company inevitably reacts to changing rules and public pressure, it has the opportunity to shift its model and become part of the legitimate housing system. But that will require transparency and co-operation, he says. B.C.’s new legislation mandates that platforms share data with the province. And increased transparency is the focus of landmark rules currently being adopted by the European Parliament, which will require that platforms verify the accuracy of property details on their listings and do random checks. 

Sears still talks to his son every night. (“He hasn’t answered, yet.”) He asks Nathan if he’s at peace and what’s on his mind. He asks what he would have done with the past year of his life—Nathan was always busy. When he was working on his master’s thesis, he was raising funds to start a watchdog NGO to monitor the sale of small arms. Through his studies in international relations and his interest in existential security, he knew that people won’t necessarily honour a treaty just because they signed it. Sears has inherited some of his son’s weariness, but his resolve as well. “Who else is going to make sure Airbnb does what it says it will?


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This story appears in the April issue of Maclean’s. You can buy the issue here or subscribe to the magazine here.