Toronto’s core is compact and the two useful subway lines cross in the middle of it, so the practical question is which line you are on.
Downtown — Financial District and Union
Beside Union Station, the CN Tower and the PATH.
Suits: short stays, business, winter visits — you can reach a great deal without going outdoors. Trade-off: it is an office district and empties in the evening. Restaurants are chains and expense accounts.
The Entertainment District and King West
West of the core, around King and John. Hotels, theatres, TIFF’s Lightbox and a dense bar strip.
Suits: nightlife, theatre, TIFF. Trade-off: genuinely loud at weekends. The King West club strip is a specific experience and rooms above it are not restful.
Old Town and the Distillery
East of the core, quieter, with the market and the Victorian streets.
Suits: walkers, and anyone who wants character without the King West volume. Trade-off: no subway station close — it is streetcars or a walk to King station.
West Queen West and Ossington
The best eating and drinking in the city, on the 501 streetcar.
Suits: anyone whose trip is about restaurants and neighbourhoods. Trade-off: no subway. The streetcar is scenic and slow.
The Annex and Bloor West
North of the university, on Line 2, with Victorian houses, Koreatown and the ROM nearby.
Suits: quiet, value, families, and anyone who wants a residential neighbourhood ten minutes from downtown by subway.
Yorkville
North of Bloor. Toronto’s expensive shopping district, with the luxury hotels.
Suits: the top end. Trade-off: priced accordingly and rather sterile.
Church-Wellesley and Cabbagetown
East of Yonge. The Village is Toronto’s gay neighbourhood and the centre of Pride; Cabbagetown beyond it is Victorian terraces and the largest such district in North America.
Suits: good value, on Line 1 or 2, walkable to downtown.
What to check before booking
Which subway line, and how far to the station. Toronto is bigger than it looks and streetcars are slow.
Noise, in the Entertainment District and King West particularly.
Air conditioning for July and August, which are humid.
The parking charge, which downtown hotels add at a substantial daily rate.
The Municipal Accommodation Tax, charged on top of the room rate along with HST — check whether a quoted price includes them.
Short-term rentals are regulated in Toronto: hosts must register with the city and may only let their principal residence. Legitimate listings display a registration number.
Seasons
TIFF in September is the peak and books out months ahead. Caribana at the start of August, Pride in late June and major conventions all spike prices.
January to March is cheapest.
The short answer
First visit: downtown or Old Town. Best all-round: the Annex. Eating and going out: West Queen West.
Apartments and hostels
Toronto has a good stock of serviced apartments, which for stays over three nights usually beat hotels — a kitchen matters in a city where restaurant bills carry tax plus tip.
Hostels cluster downtown and in the west end. Standards are reasonable.
Short-term rentals are regulated: hosts must register with the city and may only rent their principal residence, with a 180-night cap on entire-home lettings. Legitimate listings show a registration number, and enforcement is real.
Around the airport
There is a cluster of hotels near Pearson with shuttles. They are useful only for a genuinely early departure — the UP Express runs from about 5am and the airport is 25 minutes from Union, so most travellers do not need them.
The neighbourhoods to think twice about
Nothing central in Toronto is unsafe, but a few areas make poor bases. The area immediately around Yonge–Dundas Square is busy and charmless. Liberty Village, south-west of downtown, is a dense condominium district with no subway and a long streetcar ride.
Airport hotels are only worth it for a genuinely early flight, given the UP Express runs from about 5am.
The one thing that decides it
Ask yourself whether you want to walk out of your hotel into the city or take a subway to it.
If the former, stay in Old Town, the Annex or West Queen West, all of which are neighbourhoods with people living in them.
If you would rather be beside Union Station and the PATH and do not mind that the streets empty at six, the Financial District is efficient and, in January, genuinely sensible.
Seasons, restated
September is the peak because of TIFF, and hotel prices during the festival’s ten days are the highest of the year. Late June for Pride and the first weekend of August for Caribana both spike.
January to March is cheapest by a clear margin, and given how much of Toronto is indoors anyway, a winter trip costs substantially less for a largely unchanged itinerary.