This is the question almost every owner arrives with, and for a large share of them it has already been answered by the rules rather than by the arithmetic.
Start with what you are allowed to do
A City of Toronto short-term rental registration is tied to your principal residence, so a condominium you own and do not live in generally cannot run nightly. If you bought a condominium as an investment and live somewhere else, the comparison below is usually academic: mid-term is the model available to you, and the useful question is how to run it well rather than whether to run something else.
It is worth being blunt about this, because a lot of management companies will take the unit on and let you find out later.
If you genuinely have the choice
Per night, short-term wins and it is not close. Across a year, the gap narrows considerably, and for some units it closes entirely. Four things move it:
- Occupancy. A nightly unit has gaps by design. A mid-term unit on a four-month booking has none for four months
- Turnover cost. Twelve cleans a month against one a quarter is a real number, and it comes out of the same pot
- Wear. A nightly unit ages faster. Furniture, linen and paint are all on a shorter cycle, and that spend is yours
- Your time, if you self-manage. Not nothing, and usually the reason people stop
What mid-term is actually like
Fewer, longer bookings from people who need somewhere to live for a defined stretch. Relocations, contract work, medical stays, insurance placements. They arrive with dates, they mostly keep to them, and they are out of the unit during the day.
The honest downside is the gap. Two three-month stays rarely meet to the day, and a three-week hole between them is a real thing rather than something to pretend away. It is worth quoting into your expectations rather than discovering in month five.
Most units end up doing both
Where a unit qualifies for nightly letting, the pattern that works is short-term through the warm months and one long guest through the winter. That is not a compromise between the two models. It is the best available version of each, used when it is strongest.