11 Airbnbs in Toronto That Are Packed With Character

For a home away from home in Toronto, stay at a unique Airbnb
For a home away from home in Toronto, stay at a unique Airbnb | © Bill Brooks / Alamy Stock Photo
Photo of Sahar Aman
Staff Writer17 June 2019

Diverse, dynamic and dizzyingly big, Toronto is Canada’s biggest – and most multicultural – metropolis. Amid the concrete jungle, you’ll find a forest of cookie-cutter condos listed on Airbnb, but these character-packed properties will make your stay in The Six that little more special.

Oh, Toronto, home of the skyline-piercing CN Tower, the perpetually disappointing Maple Leafs (the hockey team, not the foliage) and Drake. And although Drizzy doesn’t put his pad on Airbnb when he’s off touring the world, there’s no shortage of stylish homes you can stay in when you’re visiting his hometown. From the historic row of houses of the Distillery District to the glitzy lofts of King West, Culture Trip has rounded up the coolest Airbnbs in downtown Toronto.

Vintage style apartment in the historic Annex

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Vintage Style Apartment in Historic Annex
This vintage-style apartment sleeps two guests | Courtesy of Nick / Airbnb

With stained-glass windows salvaged from the iconic Honest Ed’s discount store a couple of blocks down Bathurst Street, this one-bedroom apartment has history woven into its architecture. Heated floors, a metallic feature splashback and plenty of bespoke woodwork add contemporary comforts to this turn-of-the-century property, which is typical of the Annex, a bohemian neighborhood on the northern edge of downtown Toronto. Book this vintage apartment to stay within walking distance of the University of Toronto, the Royal Ontario Museum and the grand Casa Loma mansion. This district is also where Meghan Markle used to hang out when she lived in Toronto, so if play your cards right, you might bag yourself a prince.

Hip mid-century modern condo in trendy King West

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Hip Mid-Century Modern Condo in Trendy King West
This mid-century modern condo lies in the hip King West Village | Courtesy of Chris / Airbnb

This ground-level condo perfectly balances grunge and greenery, with its pendant lighting, polished concrete roof and distressed wooden floors overlooking a leafy private terrace through floor-to-ceiling windows that flood the living room with natural light. The industrial-chic 1950s-style furnishings suit the surrounds of the King West Village, an area that used to be the heart of Toronto’s textile industry before it began its transformation into the city’s Fashion District two decades ago thanks to a wave of upscale boutiques, galleries and eateries. It’s another affordable one-bed option just west of Toronto’s city center.

The coach house cottage near downtown

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The Coach House Cottage near Downtown
The cozy coach house cottage lies in the Leslieville neighborhood | Courtesy of Brett / Airbnb

The address says you’re only a 20-minute walk east of the skyscrapers of downtown Toronto. However, when you’re nestled on the comfy leather couch with a cup of tea and your feet up in front of the roaring fireplace, you could swear you were hiding in some remote log cabin in the Rockies. This tiny one-bedroom loft boasts more exposed timber than a virgin forest, an old-school log fire and a breezy outdoor hammock for summer. This cottage’s cozy feel extends to the neighborhood it calls home – laid-back Leslieville is littered with organic grocers, relaxed cafés, plus artisanal butchers, bakeries and cheese shops.

Play ping-pong with skyscraper views in a hip loft

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Play Ping Pong with Skyscraper Views in a Hip Loft
This large loft sleeps up to 12 people | Courtesy of Chris / Airbnb

Table tennis takes pride of place in this huge apartment smack bang in the center of the city, with the games room’s ceiling-length windows gazing out over the skyline beyond. Large groups will love this ultra-modern three-bedroom loft, which can accommodate as many as 12 guests. It comes complete with an eight-piece dining set, generous lounge area and access to a gym, pool and hot tub in the building. You couldn’t ask for a more convenient location in downtown Toronto, steps from CN Tower and the Rogers Centre across the street.

Stylish 1870s home near Distillery District and Old Toronto

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Stylish 1870s Home near Distillery District and Old Toronto
This two-level 1870s home near the Distillery District and Old Toronto features two bedrooms | Courtesy of Jay / Airbnb

From the outside, this Victorian-era property looks like all the other row houses that define the streets around Toronto’s historic Distillery District. From the inside, you’ll realize this 1870s home is one of the chicest – and most spacious – places to stay on the east side of downtown. The marble dining table, silk curtains and a Jonathan Adler chandelier provide some little touches of luxury in this charcoal-hued Airbnb. Due to its location, it’s easy to explore the mouthwatering stalls of St Lawrence Market as well as the red-brick heritage buildings and time-worn cobblestones of the Distillery District.

Feel energized in this vibrant Trinity-Bellwoods home

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Feel Energized in this Vibrant Trinity Bellwoods Home
This home is a colorful haven in Trinity-Bellwoods | Courtesy of Penny / Airbnb

While this Airbnb features eclectic furnishings, a heated-floor bathroom and a playful lounge room that’s always decorated with fresh flowers, the dazzling floral print illuminating the bedroom gives this place its mojo. And the vibrant colors don’t end in the bedroom, with brilliant shades of blue, gold and green infusing the rest of this quirky one-bedroom home. Trinity-Bellwoods – home to a large Portuguese-speaking population, and all the delectable Brazilian and Iberian restaurants that come with that – enjoys a prime downtown location, ringed by Little Italy’s pizzerias, hipster haven Kensington Market and the independent boutiques of Queen Street.

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  • Sun-kissed high-end King West condo

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    Sun Kissed High-End King West Condo © Airbnb
    This one-bedroom condo has some impressive features | Courtesy of Christopher / Airbnb

    The aesthetic of this one-bedroom condo has been taken straight out of a James Bond villain’s lair. The living room boasts a cowhide rug and a wood-burning fireplace while the opulent bathroom features a rain shower and imported Japanese toilet with a built-in bidet and a heated seat. The marble-clad kitchen has everything you could want. And then there are the jaw-dropping views, with the CN Tower practically sitting in the living room. Situated in the Fashion District on the doorstep of downtown Toronto, this sophisticated apartment is another great choice for budget travelers.

    East-downtown artist workspace in a historic building

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    This unique loft is brimming with character | Courtesy of Caroline / Airbnb

    This live-in artist workspace-turned-loft is situated on the east side of downtown – just a short walk away from the historic Distillery District. Far from Toronto’s typical tourist digs, the location offers a feel of the local life, replete with relaxed coffee shops and some of the best Vietnamese food in the city. The space is housed in a 100-year-old building and features 14-foot (4.2-meter) ceilings, exposed brick, original beams and windows that stretch the width of a wall.

    Luxury loft with views of the CN Tower

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    Luxury Loft King West
    This luxury loft in King West is ideal for a family getaway, with enough space for five people | Courtesy of Chris / Airbnb

    Located in Toronto King West’s trendy Fashion District, this stylish industrial space boasts wrap-around windows, stained-concrete ceilings and modern decor speckled with mid-century flourishes. With two bedrooms and bathrooms, this spacious loft is a perfect apartment for a group holiday or family getaway. Guests can make use of the barbecue grill if visiting during the warmer months and gaze at views of the CN Tower from the generous balcony that stretches the length of this stunning split-floor loft.

    Central Toronto penthouse with large balcony

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    This studio penthouse lies in the Fashion District | Courtesy of Ivy / Airbnb

    If you’re looking for a stylish city break in the Fashion District, this chic urban penthouse studio makes a fine choice for a group of three. This spacious and stylishly appointed condo lies just a stone’s throw away from Chinatown, giving you access to some of the best food and shopping in the city. Best of all, the flat comes with a large balcony – perfect for putting your feet up and relaxing in the late afternoon sunshine after pounding the pavements all day.

    Charming and private guest suite retreat

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    Private Guest Suite
    This private guest suite makes for an ideal couple’s getaway | Courtesy of Lauren & Shawn / Airbnb

    This secluded guest suite is conveniently located just off Bloor Street – a short walk away from Keele subway station and High Park. It’s a charming basement hideaway with a tastefully designed interior that’s reminiscent of a countryside spa retreat. The distressed wooden detail and wrought-iron bed give the space a cozy romantic feeling while the fridge and coffee-making facilities, HD TV and Bose sound system offer guests all the modern amenities they need for a comfortable stay.

    This is an updated version of an article originally created by Sahar Aman.

    These recommendations were updated on June 17, 2019 to keep your travel plans fresh.