Family-friendly vacation 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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Guest favorite
A modern living space features a green sofa paired with yellow accent chairs. Large windows provide a view of the city skyline. A kitchenette is visible, showcasing sleek cabinetry and a countertop. Natural light brightens the room, highlighting the cozy decor.
Condo in Yorkville
4.88 out of 5 average rating, 127 reviews

Scenic View! Luxury entire condo/Toronto Downtown

This unit has amazing view & Great location Luxurious area in Toronto Yorkville ! Everything is near by. Walking distance U of T campus, Royal Ontario Museum, HI-END shopping malls , restaurants and subway -1bedroom + Den -Queen bed + 2 sofa bed -High speed wifi -SmartTV (Access to Netflix or YouTube) -Cable TV -All in one Printer (Wireless) -Fully equipped kitchen (no oven) -Washer + Dryer -Iron+Ironing board -Bidet seat equipped on toilet -Gym -Paid Parking is available in the building

Guest favorite
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
4.89 out of 5 average rating, 308 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 favorite
A cozy living area features a grey sofa and two matching armchairs, all positioned on a neutral area rug. A modern arc floor lamp provides soft lighting, while framed art adorns the walls. A small glass side table sits beside the sofa, enhancing the space's functionality.
Apartment in Annex
4.93 out of 5 average rating, 211 reviews

Cute Private Apartment near University of Toronto

This cozy main floor apartment with private walk out patio, located on a quiet street in the beautiful Annex neighbourhood. Free parking Laundry in building Shared backyard 5 minute walk to subway (Christie Station) 5 minute walk to Bloor Street, the restaurants and bars of Korea Town, and historic Christie Pits Park. Walking distance to University of Toronto and George Brown College Casa Loma campus. There are a lot of great restaurants, bars and local grocery stores within a short walk.

Guest favorite
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
4.88 out of 5 average rating, 139 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.

Top guest favorite
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, 584 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 favorite
The master bedroom features a queen-sized bed adorned with a plush white comforter and a cheerful yellow accent pillow. Expansive floor-to-ceiling windows provide unobstructed views of the Yorkville skyline, allowing natural light to illuminate the space.
Apartment in Yorkville
4.9 out of 5 average rating, 109 reviews

Yorkville 29th Floor Celebrity Suite GREAT VIEW

This top floor Yorkville celebrity suite corner suite has unobstructed views of Yorkville from the Queen sized bed in the master bedroom. Steps to UofT campus, and less than 5mins walk from 3 subway stops. Luxury shopping and stores like Whole Foods, Louis Vuitton, Holt Renfrew, Nespresso, Dolce+Gabbana, Tiffany at your front door. Perfect for business or leisure. The building has a gym on the 3rd floor. The suite sleeps up to 4 people in 2 areas. The sofa bed in the living room.

Guest favorite
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, 148 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.

Top guest favorite
Home in Corktown
4.99 out of 5 average rating, 232 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 favorite
A cozy living area features a grey sofa adorned with colorful cushions, complemented by a glass coffee table sitting on a softly patterned rug. Two wooden chairs provide additional seating. Natural light filters through a nearby window, highlighting the hardwood floors.
Home in University
4.82 out of 5 average rating, 182 reviews

Two story home & garden in vibrant neighbourhood

Newly renovated heritage home in the heart of one of Toronto's most vibrant neighborhoods. Perfect for families, the home features hardwood floors, lots of natural light, and very comfy beds. Conveniently located steps from the subway on a residential street, you are close to many great restaurants & blocks from the U of T and Kensington market. Not far from Scotiabank arena & Rogers centre - for concerts and sporting events. Patio and garden are yours to enjoy. Pets welcome.

Guest favorite
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.
Condo in Yorkville
4.88 out of 5 average rating, 160 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

Superhost
A living area is presented with two blue armchairs positioned beside a low coffee table. A flat-screen TV is mounted on the wall above a gas fireplace. Light filters in through a large window, illuminating built-in shelves filled with decorative items.
Townhouse in Yorkville
4.81 out of 5 average rating, 100 reviews

Stunning Yorkville Townhome Backing onto Park

Situated in the heart of Yorkville, this 3 bedroom 2.5 bathroom townhouse with views overlooking Ramsden Park, is the ideal oasis for families, couples, or people travelling for work. The space features a bright sun-filled interior featuring a gas fireplace, WIFI, Smart TV with all apps and fully equipped kitchen. The home backs onto green space with a wonderful back deck and eating area.

Guest favorite
A bright living area features a comfortable grey sofa paired with a patterned armchair. A large mirror reflects the light, enhancing the open feel. Decorative art pieces and indoor plants add a touch of warmth, while large windows allow natural light to fill the space.
Home in Wychwood
4.81 out of 5 average rating, 179 reviews

Contemporary cozy home in the Annex

This 2 bed/2bath home is located in the more northern part of the downtown core called West Annex/Seaton Village and is on a cul de sac. Steps from TTC, Yorkville, art galleries, restos & more. The small urban-chic, clean and bright home boasts two balconies off either bed & a spacious backyard off kitchen. Permit No: STR-2010-GZSXPH Application Reference No: 3383-645

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

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

  • Total rentals

    70 properties

  • Nightly prices starting at

    R347 ZAR before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    70 properties include access to wifi

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