Holiday rentals in Old Toronto

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Top-rated holiday rentals in Old Toronto

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Loft in Little Italy
5 out of 5 average rating, 12 reviews

New! 4-Storey Loft + Terrace in Little Italy

Charming 4-Storey Loft Pied-à-Terre with Private Rooftop Terrace – Loft conversion in a historic Victorian on a tree-lined street in one of Toronto’s most beautiful neighbourhoods. Bright, airy interiors with soaring 20 ft ceilings and a lofted second floor. Live like you're a local in the heart of Little Italy — steps from cafés, restaurants, local shops, food markets and TTC, with Ossington, King & Queen West a short walk away. Enjoy this cozy retreat in the ultimate best location in the city!

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, 47 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.

Top guest favourite
Flat in Kensington Market
4.95 out of 5 average rating, 20 reviews

Bright Kensington Market studio

Quaint and cozy, second floor studio apartment in Kensington Market. Set in a vibrant community, amid shops and sounds of market bustle. Bright in the mornings and especially lively during weekends If you’re sensitive: It’s an old building. Water temp and pressure takes a brief moment to adjust, as expected. Also there is no elevator, just stairs up to the apartment. It’s not a neighborhood for people who require silence. Light sleepers may want to bring their sleep mask and ear plugs

Top guest favourite
A garden path lined with stepping stones leads to a view of the Toronto skyline across the water. Green grass and plants surround a patio table and chairs, providing a serene setting with trees framing the picturesque scene.
Cottage in Toronto
4.94 out of 5 average rating, 71 reviews

Toronto Island Cottage

This beautifully furnished, bright, and airy cottage is located just eight minutes south of the city, on the picturesque Toronto Island. This is a unique opportunity to experience all that the islands offer in a stylish setting. Perfect for a staycation or vacation, the cottage is well-equipped with everything you need to make the most of your time. The serene community is accessible only by ferry or water taxi. The view of the Toronto Harbour and skyline is absolutely epic – enjoy!

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.”

Guest favourite
A cozy living space is highlighted by a flat-screen television on a light wood media console. An armchair and a small side table are positioned nearby, with a floor lamp providing soft illumination. Natural light enters through a small window, complementing the neutral wall color.
Guest suite in Parkview Hills
4.96 out of 5 average rating, 69 reviews

Fabulous home in Toronto

Welcome Home! We are delighted to open our doors and hearts to you, inviting you to experience a stay that combines the warmth of home with the luxury of a dreamy getaway. Nestled in the heart of Toronto/East York, our charming basement apartment offers a unique blend of modern convenience and homely comfort. Whether you are traveling for business, planning a romantic escape, or embarking on a family adventure, our carefully curated space is designed to cater to all your needs.

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, 6 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, 3 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.

Top guest favourite
Home in Toronto
5 out of 5 average rating, 7 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, 174 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 !

Guest favourite
Flat in Garden District
5 out of 5 average rating, 6 reviews

Modern Condo Steps from Eaton Centre & Sonkofa Sq

Located in the heart of downtown Toronto, this stylish condo is ideal for couples, solo travelers or small groups. This 1-bedroom, 1-bathroom condo comfortably sleeps 4 guests and features a queen bed, sofa bed, 55-inch TV, and a fully equipped kitchen. With top attractions and restaurants just minutes away, you’ll enjoy both comfort and convenience in the city’s vibrant core.

Popular amenities for Old Toronto holiday rentals

When is the best time to visit Old Toronto?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price₹7,645₹7,645₹8,089₹8,623₹9,423₹10,223₹10,401₹10,667₹10,490₹9,601₹10,134₹8,356
Avg. temp-3°C-3°C2°C8°C14°C20°C23°C22°C18°C11°C5°C0°C

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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