Holiday houses 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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Guest favourite
A modern entryway features a sleek bench against a wall, complemented by a large mirror. Natural light fills the space, leading towards an open living area with tall windows and wooden flooring, creating a welcoming transition to the main living space.
Loft in Church-Wellesley
4.74 out of 5 average rating, 154 reviews

Huge 2 Storey Loft W designer furniture and art

This one of a kind penthouse in downtown Toronto has 18ft high ceilings and furnished with designer furniture and art. No parties or loud gatherings are allowed here they will get cancelled. Only 4 people are allowed up to the unit total and is monitored by 24h concierge, they will check in each guest and only allow 4 up. 3 bedrooms one upstairs just a bed 1 king bed and one queen bed upstairs. The couch could sleep 1 ontop as well but is not a bed. Fire place and true luxury art with a 75" TV

Top Guest favourite
A modern two-story cottage is surrounded by lush greenery and trees. The exterior features a combination of natural wood and dark green siding. A covered porch is visible with a personal entrance and outdoor seating. Bicycles are parked nearby, enhancing the outdoor activities available.
Guest suite in Centre Island
4.94 out of 5 average rating, 213 reviews

Cozy small newly built Toronto Islands getaway

Escape to a modern cottage on Toronto Island Looking onto Lake Ontario is our newly constructed modern home. Enjoy our cozy private guest suite in our family home with a kitchenette, ensuite bathroom, and private entrance Just a quick ferry ride from the bustling downtown core come explore the Toronto Islands which is the biggest car-free community in North America; with beaches, trails & skyline views as well as an amusement park in the summer. We also have 2 bikes you can use to explore.

Guest favourite
A warm and inviting living area features exposed brick walls and a large wooden dining table surrounded by black chairs. Soft lighting from a vintage chandelier casts a gentle glow over a cozy sofa and a stylish entertainment unit, creating a sense of comfort.
Apartment in Annex
4.94 out of 5 average rating, 118 reviews

Luxurious Annex/Yorkville 1300 Sq Ft & Parking

Beautifully appointed, top quality furnishings & amenities , spacious Yorkville/Annex rental. Full 1300 sq foot. apartment located within a Heritage Victorian Brownstone! Exceptionally located, walking distance to subway, restaurants and all the sights! Walk to Casa Loma, Royal Ontario Museum & Yorkville. Parking, Wifi, Chromcast, Fibe TV, Local High Def TV included. Fully equipped gourmet kitchen. Air Conditioned. Digital safe for valuables. Treat yourself to pantry snacks, coffee & tea.

Top Guest favourite
A well-lit living area features a large window draped with light curtains, allowing natural light to fill the space. A stylish sectional sofa is positioned beside a contemporary coffee table adorned with decorative glass pieces. A TV and chest of drawers complete the inviting setting.
Home in Downtown Toronto
4.99 out of 5 average rating, 133 reviews

Stylish Home in Downtown Toronto, Walkable area

Discover Toronto from our newly renovated, spacious apartment with a private balcony on Queen Street W! Steps to trendy spots (bars, restaurants, attractions, groceries, LCBO) and easy streetcar access for city exploration. Enjoy morning Nespresso™ coffee with CN Tower views on the balcony. Key Locations: 2 mins walk to Queen St W and Portland St 8 mins walk to King St W and Portland St 13 mins walk to Trinity Bellwoods Park 13 mins walk to Art Gallery of Ontario 10 mins drive to CN Tower

Guest favourite
Apartment in Entertainment District
4.92 out of 5 average rating, 125 reviews

Stunning Skyline View Condo, Steps to CN Tower

Stay in the heart of downtown Toronto in this modern one-bedroom condo just steps from the CN Tower, Rogers Centre, and the waterfront. The unit features a comfortable queen bed in the bedroom and a sofa bed in the living room, perfect for couples or small groups. Enjoy skyline views through floor-to-ceiling windows or relax on the private balcony. The condo includes a full kitchen, smart TV, high-speed Wi-Fi, and in-suite washer and dryer. Guests also have access to a gym and outdoor pool .

Guest favourite
Apartment in Entertainment District
4.92 out of 5 average rating, 122 reviews

Toronto style condo

Welcome to Toronto! This spot is located in a prime location for all your travel needs. Great for a business or leisurely trip. We are located 5 minutes from the Rogers Centre/CN Tower, TIFF, and much more! BTW, Toronto's Nobu is next door! The bathroom is fully equipped, and the kitchen is fully stocked with everything you'd need to cook/bake for your and your family. We are close to public Transportation such as Streetcars & Subways outdoor/ indoor dining in the Entertainment District.

Top Guest favourite
A bright living room is highlighted by a cozy sofa and a sleek coffee table. Two yellow chairs face large windows, allowing natural light to fill the space. A flat-screen TV is mounted on the wall, and a decorative plant adds a touch of greenery.
Home in Roncesvalles
4.99 out of 5 average rating, 179 reviews

Luxury modern Victorian - private parking included

This recently renovated gem has all of the comforts of home, with a fully appointed kitchen that has everything you need to cook a great meal. Nespresso coffee and a selection of teas are also included. Two Smart TVs and a Bluetooth speaker for entertainment. Two comfortable beds and a spacious spa bathroom will make your stay feel like home. A work remote work set up is available for those who require it. The private backyard includes a gas BBQ and private parking is included.

Top Guest favourite
A sunset over the water is portrayed, with a golden sun reflecting on the calm surface. The horizon features a silhouette of trees, creating a serene atmosphere. Soft waves ripple gently in the foreground, enhancing the tranquil setting.
Apartment in Centre Island
4.95 out of 5 average rating, 110 reviews

Toronto Island Wonderland View

Toronto Islands are a 10 minute ferry ride away from downtown Toronto. Switch from the hustle and bustle of the city to the tranquillity of one of Toronto's most coveted parks. Unique to any other metropolitan city, Toronto Island has limited vehicle access. This car free area boasts 6 kilometres of nature walks, children and pet friendly access to beaches, Centre island amusement park, artist exhibitions, restaurants and even a nude beach. A perfect getway for the hybrid vacationer.

Guest favourite
An outdoor seating area is showcased, featuring a comfortable couch adorned with patterned cushions. Flanking the couch, two red chairs face a wooden fence, while a decorative lantern and potted plants add touches of greenery, highlighting the inviting atmosphere of this private space.
Home in Cabbagetown
4.94 out of 5 average rating, 597 reviews

Comfy Oasis In Historic Downtown Neighborhood

According to Airbnb, we are "One of the most beloved homes on Airbnb". Now in the top 5% of all listings on AIRBNB. Superhosts for 10 years! This renovated guest house features an open-plan kitchen, a spiral staircase to a beautiful and open loft suite, with custom furniture and decorating accessories (1 bed + 1 sofabed). Enjoy the beautiful garden in the summer, and sip any of the more than 15 different complimentary teas and coffees we offer. This guest house is FULLY equipped.

Guest favourite
A spacious sleeping area is furnished with a large bed covered in a white quilt, accompanied by neatly arranged towels. A desk with a computer is positioned nearby, while a decorative rug adds texture to the polished concrete floor. Exposed brick walls provide a touch of character.
Apartment in Cabbagetown
4.93 out of 5 average rating, 175 reviews

Modern Victorian

Modern stay in a Cabbagetown Victorian. Welcome to our renovated, self-contained basement apartment in the heart of Cabbagetown, Toronto. This chic space is ideal for solo travelers or couples. Our apartment is nestled in the charming Cabbagetown neighborhood, known for its Victorian houses, tree-lined streets, and vibrant atmosphere. Cafes, restaurants, and boutiques are within walking distance, and nearby parks offer tranquil escapes. Book now to experience the best of Toronto.

Guest favourite
A spacious living area features a light-colored sofa facing a large window, with natural light filling the space. A modern staircase leads to the upper level. Textured stone walls add depth, and a small wooden table is positioned next to a comfortable chair.
Loft in Entertainment District
4.83 out of 5 average rating, 269 reviews

Amazing 2 Storey Loft 3 BED In Central Downtown

This unique 2 storey loft is super stylish and a rare find in downtown Toronto. This two storey loft has amazing 9 foot high ceilings finished fully modern kitchen and bathrooms. This super luxurious loft is perfect for nights out or gatherings. Ottoman in the living room is a pullout as well as the chair upstairs in the bedroom, just inform if you want setup and the air bed in the master upstairs is also a twin Equipped with a balcony.

Top Guest favourite
Home in Corktown
4.99 out of 5 average rating, 245 reviews

Stylish 1870s Home near Distillery District & Old Toronto

Steps from the Distillery District this Top 1% listing is a beautifully restored 1870s row-house that blends historic charm with modern refinement. Thoughtfully designed throughout, it’s located at the Distillery District, St. Lawrence Market, and some of the city’s best cafés and restaurants. In the evening, unwind in the serene, charcoal-toned bedroom beneath the warm glow of a statement chandelier—your refined Toronto retreat awaits

Popular amenities for Old Toronto holiday rentals

When is the best time to visit Old Toronto?

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Avg. price$147 NZD$147 NZD$156 NZD$166 NZD$181 NZD$197 NZD$205 NZD$210 NZD$198 NZD$183 NZD$169 NZD$166 NZD
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Quick stats about holiday rentals in Old Toronto

  • Total holiday rentals

    Explore 16,850 holiday rentals in Old Toronto

  • Verified guest reviews

    Over 538,960 verified reviews to help you choose

  • Family-friendly holiday rentals

    5,610 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 3,230 rentals that welcome pets

  • Holiday rentals with a pool

    2,620 properties feature pools

  • Rentals with dedicated workspaces

    9,230 properties have a dedicated workspace

  • Wi-Fi availability

    16,570 of Old Toronto holiday rentals include Wi-Fi 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 Scotiabank Arena

Destinations to explore

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