Family-friendly holiday rentals in The Annex, Old Toronto

Find and book unique family-friendly homes on Airbnb

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.
Apartment in Yorkville
4.9 out of 5 average rating, 314 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.

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, 220 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.

Top guest favourite
Home in Downtown Toronto
4.99 out of 5 average rating, 248 reviews

Stylish 1870s Home near Distillery District & Old Toronto

Visiting for fifa? Stop here...Steps from the Distillery District downtown, this Top rated listing is a beautifully restored 1870s row-house (townhouse) that blends historic charm with modern refinement. Thoughtfully designed throughout, it’s located downtown also close to 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

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.
Flat in Midtown
4.85 out of 5 average rating, 109 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.

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
4.86 out of 5 average rating, 109 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.
Apartment in Yorkville
4.93 out of 5 average rating, 208 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.

Guest favourite
A glass table is positioned near large windows, offering an unobstructed view of the city skyline. Two modern chairs are placed around the table, with a small potted plant and a decorative item enhancing the scene. The background features tall buildings and hints of greenery.
Apartment in Yorkville
4.89 out of 5 average rating, 173 reviews

Steps to Four Seasons Hotel Yorkville Condo

Unobstructed panoramic view in the heart of upscale Yorkville. Minute walk to Bay subway station, Whole Foods, ROM and U of T and high-end restaurants. Easy parking @ 74 Yorkville for $20 (daytime). Around the corner from Toronto's main luxury shopping hub, Yonge + Bloor. *Upscale neighborhood *Highspeed WIFI *Walk score of 96 *Transit score of 93 *Bike score of 98 (rentable Bixi bikes nearby) *Fully equipped kitchen *Full-sized washer/dryer *Gym in building

Guest favourite
Home in Downtown Toronto
4.9 out of 5 average rating, 131 reviews

Beautiful, bright 1 Bedroom in Victorian Home!

Feel at home in the heart of Toronto in this beautifully renovated century old Victorian main-floor suite on a quiet Kensington Market street. Enjoy an incredible bright solarium, spacious living room, fully equipped galley kitchen, and large bedroom with a king size bed. Private furnished backyard to enjoy. Walk to Kensington Market, Chinatown, Little Italy, U of T, and major hospitals. A stylish, comfortable home base perfect for exploring the city.

Top guest favourite
A bright living area features a navy sofa bed positioned across from a black TV stand with a flat-screen television. Natural light floods in from the sliding glass doors that lead to a balcony, with greenery from a nearby plant adding a touch of nature.
Apartment in Downtown Toronto
4.91 out of 5 average rating, 235 reviews

Cozy space in one of Toronto's best neighbourhoods

My place is a clean and quiet spot in the heart of Toronto's entertainment district. Location, location, location! Access the CN Tower, Ripley's Aquarium, The Royal Ontario Museum, The Art Gallery of Ontario and many more within a short walk or commute. The neighbourhood contains many restaurants and bars showcasing Toronto's cuisine and culture. My place is in the King West neighbourhood of downtown Toronto and is very convenient to access.

Guest favourite
An impressive view of a modern high-rise building is captured from below, showcasing the architectural details of the glass façade and concrete structure. A bronze statue stands prominently at the base, adding a cultural element to the urban landscape.
Apartment in Yorkville
4.9 out of 5 average rating, 182 reviews

Yorkville Toronto Breakfast Included

Entire apartment is yours to enjoy. I am the owner: I always clean-this is not multi operated. Laundry is carefully cleaned. New leather reclining sofa. I include breakfast groceries at no charge. Coffee, tea, milk, 2 apples, 2 oranges, 2 bananas, 4 bagels, cream cheese, strawberry jam, dozen eggs, butter, onion, tomatoes. Walk to Whole Foods, Starbucks. University.50" TV + 32 " TV, includes NETFLIX, AMAZON PRIME VIDEO, INTERNET.

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.
Flat in Midtown
4.97 out of 5 average rating, 102 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, 264 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.

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

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

  • Total holiday rentals

    Explore 80 holiday rentals in The Annex, Old Toronto

  • Nightly prices starting at

    The Annex, Old Toronto holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,090 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    80 of The Annex, Old Toronto holiday rentals include wifi 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 Spadina Station

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