Family-friendly holiday rentals in The Annex, Old Toronto

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in The Annex, Old Toronto

  • Total holiday rentals

    Explore 70 holiday rentals in The Annex, Old Toronto

  • Nightly prices starting at

    The Annex, Old Toronto holiday rentals start at $29 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,210 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 of The Annex, Old Toronto holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across The Annex, Old Toronto rentals

  • 4.8 Average rating

    The Annex, Old Toronto stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    The Annex, Old Toronto's top spots, include Royal Ontario Museum, Bata Shoe Museum, and Bathurst Station

Top-rated family-friendly rentals in The Annex, Old Toronto

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite
A modern suite features a spacious bed with a tufted headboard, complemented by light-colored bedding. A glass partition delineates the living area, which includes a round dining table and comfortable seating beneath large windows. A sleek workspace with a printer is also present.
Condo in Yorkville
4.9 out of 5 average rating, 319 reviews

Luxury Yorkville Escape | Condo in Prime Location

Discover refined living in this beautifully furnished apartment in Yorkville Toronto’s most glamorous & exclusive neighborhood. With new furniture & modern appliances, this space blends comfort with sophistication. Step outside and find yourself surrounded by luxury boutiques, acclaimed restaurants, chic cafes, & world-class art galleries. With Bay subway station just a 3 minute walk away, the entire city is at your fingertips. Elevate your lifestyle in a place where elegance meets convenience.

Guest favourite
The exterior of a tall, modern building is captured from a low angle, highlighting its sleek design and illuminated upper floors. A bronze sculpture of a horse stands prominently in front, set against expansive glass walls reflecting city views.
Apartment in Yorkville
4.9 out of 5 average rating, 115 reviews

Sweet Home in Yorkville, Toronto, free parking

Welcome to your home at Yorkville Plaza in the heart of downtown Toronto! Formerly the Four Seasons Hotel Condo, this suite has been newly furnished. The main bedroom is full of natural light and the den serves as a second bedroom or office. The living room sofa can be turned into a huge bed. You can sit beside fireplace or cook in the kitchen; you can watch spectacular city views or enjoy comforts from smart TV to smart toilet. Walking around in the historical old Yorkville Village is joyful!

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 Toronto
4.95 out of 5 average rating, 241 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
Condo in Downtown Toronto
4.95 out of 5 average rating, 172 reviews

Beautiful Petit Gem Ap. In Downtown! Walk Anywhere

Welcome to our lovely petit aparment in heart of downtown Toronto! Our place has everything you might need in order to enjoy the city, work remotely and have a great time when the weather outside is not the best! Located right in downtown, you can basically walk anywere fast: Eaton Centre, Dundas Square, U Toronta, etc. Enjoy many of the high end stores located in the area and also some of the best restaurants! The entire place is sensitized using UV lights and COVID 19 cleaning solutions.

Guest favourite
A spacious sleeping area features a brand new bed with a quilted beige coverlet, complemented by two bedside lamps. Exposed brick walls add character, while colorful artwork hangs above the bed. A cozy sofa is visible to the side, enhancing the inviting atmosphere.
Guest suite in Little Italy
4.89 out of 5 average rating, 184 reviews

Loft-Style Private Studio Little Italy/Ossington

From the exposed brick, to original artwork, to massive private bathroom with double vanity, this basement suite in our home has been renovated and decorated to feel like a loft. The double bed is brand new with a 16" mattress sure to deliver an excellent night's sleep. You will find a brand new, 42" smart TV resting on a unique mantlepiece refashioned from an antique upright piano, as well as a kitchenette with convection oven/air fryer, Keurig coffeemaker, and stainless steel mini fridge.

Guest favourite
A modern living area features a dark gray convertible sofa and a small dining table near the windows. Natural light enters through two large windows, framed by light curtains. A well-equipped kitchen is visible in the background, showcasing stainless steel appliances and a white countertop.
Apartment in Midtown
4.86 out of 5 average rating, 119 reviews

Cozy 1 Bedroom Unit in the Annex, Free Parking

Welcome! This cozy unit is a great place to stay if you want to be in the city without feeling like you're in a concrete jungle. Located in the Annex, it's a food haven for those that are interested in exploring different places to eat. It's also a 5 min walk away from the Bloor/Spadina subway station (or Bathurst station in the other direction), so it's great for commuting around to different areas of Toronto. Yorkville, the ROM, and Casa Loma are also under 10 mins drive from here.

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 Toronto
4.96 out of 5 average rating, 121 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.

Top Guest favourite
A cozy sleeping area is presented with a spacious bed, featuring soft bedding and decorative pillows. Nightstands flank the bed, providing small plants and ambient lighting. A calming nature print is displayed above the bed, enhancing the serene environment.
Home in Midtown
4.87 out of 5 average rating, 122 reviews

Annex Haven: 1 Bedroom plus Den

This centrally located private space is newly updated with new flooring, furniture, and bathroom. It includes a separate entrance with its own kitchen and laundry. Very quiet residential neighbourhood with old growth trees. Walking distance to Christie subway station or Dupont subway station. Be downtown within 20 minutes. Close to Koreatown and many great restaurants on Bloor Street. 5 min walk to 4 grocery stores and LCBO. Basement space not suitable for people over 6 feet tall.

Guest favourite
A stylish living space features an eye-catching geometric wallpaper, complemented by a contemporary wooden sideboard and a gray sectional sofa. A small round table and a two-person bar table are positioned near large windows that offer expansive city views.
Condo in Yorkville
4.93 out of 5 average rating, 218 reviews

Beautiful 1 Bedroom Yorkville Condo w/ Parking

Pamper yourself with everything Yorkville has to offer with this professionally decorated, NYC inspired condo at the heart of Toronto's most exclusive address with complimentary valet parking. Queen size bed, sofa bed in living room, 2 person bar table, work station and a 55" Smart TV to accommodate all your needs. Contemporary art by local artist throughout with high end furniture and Miele appliances. South facing lake/city views through expansive floor to ceiling windows.

Top Guest favourite
A dining area is presented with a wooden table set for meals. A textured vase holds an arrangement of greenery and foliage. Black-framed photographs adorn the wall, creating an artistic backdrop, while a pendant light offers soft illumination.
Apartment in Midtown
4.97 out of 5 average rating, 111 reviews

Renovated Modern 2 Bedroom Suite w/ City Views

Experience the city like a local in this newly renovated two-bedroom suite. This ample, bright, airy space has beautiful city line views. We are centrally located (steps away from Casa Loma and downtown) with plenty of options for food, drinks, and local shops. The area has excellent walkability and great transit access. 24km from/to Pearson Airport and 6km from/to Billy Bishop Airport

Guest favourite
The living room features a spacious leather sectional sofa facing a central coffee table. Natural light fills the area through multiple large windows. A brick fireplace adds warmth, while a staircase with glass railing leads to the upper levels. Potted plants bring a touch of greenery.
Home in Midtown
4.88 out of 5 average rating, 270 reviews

Bright, Stunning Victorian Townhouse in the Annex

Newly renovated, 3 level, 2-bedroom sun-filled unit, situated in the Annex. Brick fireplace, central air conditioning and heating, wooden floors and exposed brick. Steps away from Bloor St, coffee shops, restaurants, shops, galleries, parks and much much more. Short walk to Bathurst and Spadina Subway, Casa Loma, Yorkville, University of Toronto, and museums.

Top Guest favourite
A spacious outdoor deck is furnished with a large sectional couch and a glass table. The well-maintained garden is bordered by wooden fencing, featuring a lush green lawn, flowering plants, and a hammock hung between two trees, with a children's playhouse visible in the background.
Apartment in Midtown
4.98 out of 5 average rating, 101 reviews

Main fl Annex, private garden oasis, welcome dogs!

Entire main floor of a beautiful 100-year-old Victorian house with incredible 100-foot-long PRIVATE garden oasis - great for dogs!. Located in the heart of the Annex, one of Toronto’s oldest and most vibrant neighbourhoods with stately homes, leafy streets and loads of hip bars, cafes, and restaurants.

Popular amenities for The Annex, Old Toronto family-friendly rentals