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The City of Boston is ramping up enforcement of some of the nation’s toughest rules on the booming short-term rental industry. And already officials have issued about 400 fines for violations.

City officials have cited nearly 200 addresses — from Seaport apartment towers to handsome Back Bay brownstones to modest two-families in Roslindale — for breaking new rules that effectively ban landlords from renting apartments by the night to tourists on platforms like Airbnb.

Now, on the eve of a Dec. 1 deadline for legal short-term rental hosts to register with the city, officials are watching to see if the regulations have the desired effect of easing Boston’s housing crunch by putting apartments that have become “de facto hotels” back into the general rental market.

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As of this week, about 700 people had been approved as hosts, under rules that allow short-term rental of spare bedrooms, owner-occupied units up to 90 nights a year, and extra units in owner-occupied two-families and three-deckers, said Dion Irish, the city’s commissioner of inspectional services. About 200 more have applications pending.

That’s a fraction of the 6,100 units in the city listed earlier this year on Airbnb. Irish said that’s an indication the rules, which essentially ban landlords from renting their apartments by the night, appear to be working.

“That’s exactly what we thought would happen,” he said. “This ordinance doesn’t prevent short-term rentals in Boston. It just restricts who can operate.”

The restrictions are aimed primarily at landlords and building owners who take apartments out of the general rental market and lease them instead to tourists — often a more lucrative proposition. That’s what owners of most of the 208 properties that have been fined since the rules took effect Sept. 1 were doing, Irish said.

He said he was hopeful the prospect of fines and a new partnership with Airbnb — starting Dec. 1 it will require hosts to display city registration numbers — will deter would-be scofflaws. The fines are $300 per violation.

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Still, advocates of the regulations note that other cities that have enacted tough new rules, including Cambridge, have sometimes struggled with enforcement. Determined operators who know how profitable short-term rentals can be will keep seeking ways to quietly continue, said Ford Cavallari, chairman of the Association of Downtown Civic Organizations.

“This whack-a-mole game is going to be really tough,” he said at a recent City Council hearing. “There’s going to be a lot of mole heads popping up, and we’ll need a lot of paddles to whack them back down.”

But the Boston rules appear to be making a difference.

Several large short-term rental operators in the city say they’re managing fewer units than they used to. Owners of big apartment buildings that have leased entire floors to corporate-housing providers have wound down at least some of those contracts, though several declined to be interviewed. And city officials say they’re optimistic that hundreds, perhaps thousands, of apartments that had been used as short-term rentals will go back into the general housing market, perhaps helping to curb rising rents.

That is the hope of housing advocates and neighborhood activists who, along with Boston’s hotel workers union, spent years pushing the City Council and Mayor Martin J. Walsh to crack down on short-term rentals. In 2018 they did, and in August the city settled a lawsuit by Airbnb challenging the regulations, which cleared the way for full enforcement.

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“You had these de facto hotels that were driving up housing prices, causing problems with late-night parties, trash, parking,” said City Councilor Ed Flynn, who represents Chinatown, the South End, and other neighborhoods where there have been many short-term rentals.

“This is a compromise that will help make sure Boston is always a city for everybody.”

But that compromise does not come without some victims.

As the short-term rental industry grew, it birthed a wave of small companies — property managers, bookers, cleaners — who specialized in the high-volume, quick-turnover business of readying apartments for new guests. Those people say they’re being clobbered by the strict limits on rentals.

Recognizing a need to accommodate families in town for a relative’s long-term hospital stay, Kama Cicero four years ago launched STARS of Boston, which eventually managed about 30 units for owners of small properties around the city.

Now the company is down to about 20 units, Cicero said, that often sit empty because the rules typically require a 28-night stay — far longer than most visitors need. That means less work for Cicero and the 10 people she hires to book, manage, and clean the properties.

“I can’t sleep at night. We have all these vacancies,” Cicero said. “Every month we’re going deeper and deeper into the red.”

Some of Cicero’s larger competitors are trying to find ways to exist within the new rules.

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Sonder, a San Francisco firm that at one point managed more than 300 short-term rentals in Boston, let go of about 125 units as the regulations took effect. Sonder wants to reclassify the rest as “executive suites,” a separate zoning category that allows for short stays but mandates hotel-level safety and disability access standards, and is seeking city permission to do so.

“We’ve spent over $500,000 making sure we can do the upgrades we need,” said Mason Harrison, a spokesman for the company. “We just want certainty.”

But some, like Flynn, worry that sort of reclassification is just a loophole that will entrench short-term rentals in buildings that are supposed to be helping to ease the housing crunch.

“That runs contrary to the spirit of the ordinance and would basically allow hundreds of units to continue like this,” he said. “We have to be very careful about approving exemptions.”

Irish agreed, and said that while there are legitimate, longstanding needs for short-term rentals — for hospital stays, visiting researchers, or business travelers in town for a few weeks — the business of renting apartments hotel-style to tourists en masse “will cease.”

He was optimistic that the new partnership with industry giant Airbnb — the result of months of legal wrangling — would help, as would a statewide registry being launched this year.

“People who are doing this should understand that we have a lot of effective enforcement tools at our disposal now,” he said. “They have to find a way to comply with the rules, or find a new line of business.”

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Tim Logan can be reached at tim.logan@globe.com. Follow him on Twitter at @bytimlogan.