Toronto: registered, principal residence only, 180 nights.
Toronto's regime is the most publicized and the most mature. Short-term rentals under 28 days are permitted only in your principal residence, you must register with the city and renew annually, the registration number must appear on every listing, an 8.5 per cent Municipal Accommodation Tax applies, and entire-home rentals are capped at 180 nights per year. Fines for operating outside the rules reach $10,000 per offence for individuals.
We cover Toronto's rulebook in detail in our dedicated guide. The one-line version: fully workable for owner-occupants, closed for investment units under 28 days.