Holiday rentals in Old Toronto

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Top-rated holiday rentals in Old Toronto

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Top guest favourite
The exterior of the laneway house features a modern design, characterized by large windows and a dark facade. It is surrounded by mature trees and a well-maintained yard, creating a serene atmosphere. A stone pathway leads to the entrance, inviting guests into the space.
Home in Parkdale
5 out of 5 average rating, 48 reviews

Stylish Oasis: an architect's unique laneway house

Come and experience our laneway house in the heart of Parkdale, Toronto! This brand new (2022) laneway house has been beautifully designed by the homeowner/architect with amazing attention to detail. It is modern and bright with windows on all 4 sides of the house. It’s inviting, clean and nestled in a park-like setting. It’s also completely private and quiet. Close to Roncesvalles Ave, High Park, Sunnyside Beach, Queen Street and venues such as BMO Field, Exhibition, and the Budweiser Stage.

Guest favourite
Home in Summerhill
5 out of 5 average rating, 10 reviews

Summerhill Designer 2BR Home • Must See • Sleeps 4

✦ Design-forward retreat with a sunlit living room—large leather sofa, lounge chairs, wall-mounted TV, and a sleek linear fireplace. Glass-top dining for four flows to a chef-ready galley kitchen with wall oven, quartz counters, and a breakfast bar for two; slide the doors to a private, greenery-framed deck. Two serene bedrooms (king + queen). Spa bath with walk-in shower, and soaking tub. In-home laundry, hardwood floors and fast Wi-Fi. Modern and thoughtful decor—perfect base for your stay.

Top guest favourite
The living area features a modern design with a comfortable sofa accented by patterned pillows. A marble dining table is surrounded by elegant chairs. A striking chandelier hangs above, while a large round mirror reflects the ambient light from windows dressed in soft curtains.
Home in Corktown
4.99 out of 5 average rating, 236 reviews

Stylish 1870s Home near Distillery District & Old Toronto

“Rated a Top 10 listing by BlogTO and frequently featured as a must-stay in Toronto. Love thoughtful details? You’ll find them here in this stylishly remodeled 1870s rowhouse. Start your day at St. Lawrence Market, wander through the pedestrian-friendly Distillery District, and explore nearby cafés, restaurants, and bars. In the evening, retreat to the plush, charcoal-hued bedroom and drift off under the glow of a tiered Restoration chandelier. The perfect Toronto stay awaits.”

Top guest favourite
A stylish living room is filled with various plants and natural light. A comfortable sofa is flanked by two chairs, with a small coffee table in front. A large artwork is displayed on the wall, and a decorative rug is laid on the floor.
Flat in Annex
5 out of 5 average rating, 42 reviews

Grande Victorian Retreat

Enjoy a stylish, luxury experience at this centrally located apartment on the main floor of a Victorian home. Walking distance to CasaLoma, Royal Ontario Museum, University of Toronto, Yorkville Village Shopping! Only a 2 minute walk to the TTC. The space Living Room: Smart TV and High-speed internet. Bedroom: Queen-sized bed, large walk-in closet, Smart TV. Kitchen: Fully-stocked to make your extended stay feel like home. Bathroom: Large walk-in shower, Washer dryer unit.

Guest favourite
Flat in Toronto
5 out of 5 average rating, 7 reviews

Charming Designer Suite in Leslieville

This walk-out lower-level suite feels airy and inviting, with portions above grade and 7-foot ceilings that fill the space with natural light. Recently designer-renovated, it features brand new flooring, a sleek modern kitchen, and thoughtful decor throughout. Just a 30-second stroll to the streetcar, nestled on a quiet, tree-lined street. A short walk from the heart of Leslieville with trendy restaurants, quirky coffee shops & breweries, plus right across from Greenwood Park.

Flat in Playter Estates-Danforth
5 out of 5 average rating, 4 reviews

Digs on Danforth

Enjoy easy access to everything from this perfectly located home base. In a quiet residential area steps from bustling greektown, on the subway line, walk to restaurants, coffee, bars, live music etc. Separate entrance to bright, newly renovated one bedroom basement apt. fridge, hot plate, toaster oven, microwave. Washer/Dryer. Parking available if needed. * basement apt with separate entrance; family with small kids live upstairs. Only registered guests allowed in the suite.

Guest favourite
Private room in Annex
4.94 out of 5 average rating, 777 reviews

Downtown Toronto Private Apartment in the Annex

This 1900s vintage-style modern private apartment is in the lower part of our house in the Annex which showcases stained-glass windows from the famed Honest Ed's store. No part of this space is shared. Heated floors, AC provide comfort year round. Summerhill Market for freshly prepared meals and salads is in the next block across the street. Close to Bathurst subway and bus station. Free underground parking, 3.1 KM away. Paid parking at 10 Walmer Rd. Parking is 1.5 KM away.

Top guest favourite
Private room in Dovercourt Village
4.94 out of 5 average rating, 291 reviews

The GREEN Room in the trendy Ossington-Bloor area

The Green Room (with no kitchen or laundry but with a small fridge, kettle & coffee maker) is spacious and beautifully decorated. We are a 5 minutes walk to the subway and everything is in this area - all types of restaurants, cafes, a mall, trendy stores, etc. If you like to walk, you can walk downtown, to Chinatown, Koreatown, the UofT, even High Park. I love meeting people from all over and will be available to talk and help you out as needed.

Superhost
Flat in Entertainment District
5 out of 5 average rating, 4 reviews

Unbeatable Location, Endless Vibes, CN Tower View!

This modern condo in Toronto’s King West neighbourhood offers a private, peaceful escape in the heart of the city. Walk to the Entertainment District, Rogers Centre, and the trendy shops and dining spots on Queen Street. Professionally decorated and cleaned between each stay, you’ll enjoy a fresh, stylish retreat with no shared spaces. Perfect for those seeking comfort and convenience in downtown Toronto.

Guest favourite
A modern living area showcases floor-to-ceiling windows offering city views. A sleek black sofa with decorative cushions is paired with two white chairs. A marble feature wall serves as a backdrop for a fireplace, complemented by a round coffee table accessorized with decor.
Flat in Entertainment District
5 out of 5 average rating, 23 reviews

Rare One of a Kind Sub-Penthouse + Parking

Welcome to our luxurious downtown sub-penthouse retreat. Designed with comfort and style in mind, this spacious home features two queen beds and a cozy sofa bed, making it ideal for families or groups. Enjoy cooking in the sleek, fully equipped kitchen, and unwind with modern amenities throughout. Whether you're visiting Toronto for business or leisure, this is the perfect home base for your stay.

Top guest favourite
Home in Toronto
5 out of 5 average rating, 10 reviews

Cozy Modern Studio in Toronto’s Upper Beaches

Bright Modern Studio in Upper Beaches Enjoy this newly renovated, cozy studio with a full kitchen, private bathroom, and separate entrance. Bright, quiet, and modern, it’s perfect for one or two guests. Includes in-unit laundry, Wi-Fi, and all essentials. Located in a peaceful Upper Beaches neighborhood, close to cafés, parks, transit, and the lake — your relaxing Toronto getaway awaits!

Top guest favourite
Private room in Davisville Village
5 out of 5 average rating, 176 reviews

Mid town Toronto LGBTQ Friendly Chic & Comfortable

This urban chic place is perfect for solo, or couples/friends on vacation or business. Centrally located in mid-town Toronto between two subway stops (St Clair and Davisville on Line 1) plus 24 hour bus service, you are only 15 minutes from downtown or a 8 minute drive. On street parking is free! I look forward to hosting you in Toronto, the world’s most multicultural city !

Popular amenities for Old Toronto holiday rentals

When is the best time to visit Old Toronto?

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Avg. price$112 SGD$112 SGD$118 SGD$126 SGD$138 SGD$150 SGD$156 SGD$160 SGD$151 SGD$141 SGD$148 SGD$122 SGD
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Quick stats about holiday rentals in Old Toronto

  • Total holiday rentals

    Explore 16,330 holiday rentals in Old Toronto

  • Verified guest reviews

    Over 522,810 verified reviews to help you choose

  • Family-friendly holiday rentals

    5,340 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 3,090 rentals that welcome pets

  • Holiday rentals with a pool

    2,540 properties feature pools

  • Rentals with dedicated workspaces

    8,900 properties have a dedicated workspace

  • Wifi availability

    16,070 of Old Toronto holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Old Toronto rentals

  • 4.8 Average rating

    Old Toronto stays are highly rated by guests – averaging 4.8 out of 5!

  • Nearby attractions

    Old Toronto’s top spots include CN Tower, Rogers Centre and Toronto Eaton Centre

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