Family-friendly holiday rentals in Rosedale

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Rosedale

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

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Top guest favourite
The exterior of the duplex house is shown, featuring a well-maintained front lawn with blooming flowers. The building has a brick façade with large windows framed by vibrant greenery. A small balcony is visible on the upper floor, adorned with potted plants.
Home in Deer Park
4.97 out of 5 average rating, 118 reviews

2-Bedroom House In Deer Park

Welcome to our charming 2-bedroom duplex house nestled in the beautiful Deer Park neighbourhood of Toronto! This cozy Airbnb is the perfect home away from home for your stay in the heart of the city, with subway, shops and parks within 10 minutes' walk. This newly renovated house is on the ground floor of a duplex and boasts an amazing sun-room, beautifully furnished living and dining rooms, a fully equipped modern kitchen and 2 comfortable bedrooms. Parking and laundry is available on request.

Top guest favourite
A bright guest suite features a queen-size bed with a light coverlet, complemented by a cozy couch and additional seating. Warm yellow walls create a welcoming atmosphere, while a door leads to the exterior. Natural light is welcomed through a nearby window.
Guest suite in Davisville Village
4.91 out of 5 average rating, 318 reviews

Mid-town T.O. getaway - conveniently located

Bright and spacious lower guest suite for singles or couples. Very safe family neighbourhood, close to public transit (TTC), restaurants, theatres, Sunnybrook Hospital for medical staff or patient visitors. Queen-size bed, couch, TV (with Netflix, AppleTV, Prime Video, no cable), private full kitchen and bathroom. All towels and linens provided. Shared laundry machine. 12 min walk to Yonge St. and Subway, 2 min walk to bus stop (6 mins to Yonge by bus), 25 mins from downtown on public transit

Top guest favourite
A bright living area is highlighted by large floor-to-ceiling windows, allowing ample natural light. A comfortable gray couch adorned with throw pillows faces a glass coffee table. A large mirror reflects the space, while a minimalist bookshelf adds a stylish touch.
Loft in Fashion District
4.96 out of 5 average rating, 366 reviews

Spacious 1BR Loft • High Ceiling • Walk Everywhere

A bright and stylish urban loft in the heart of downtown! This sun-filled suite features soaring 12-ft ceilings, stunning floor-to-ceiling windows, and sleek hardwood floors. Relax on the oversized sofa, dine at the modern table, and cook in the fully stocked kitchen with stainless steel appliances. Sleep soundly on a plush Westin Heavenly queen bed, and refresh in the spa-like marble bathroom. Includes in-suite laundry, high-speed Wi-Fi, and an unbeatable location near vibrant King Street West!

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
4.94 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.

Top guest favourite
A cozy living room is illuminated by natural light, featuring a modular grey sofa with vibrant orange and white accents. A modern gas fireplace provides warmth against a textured wall, while shelves display books and decor. A flat-screen television is mounted above the fireplace.
Home in East Danforth
5 out of 5 average rating, 100 reviews

Central Family Friendly 3BR | Steps to Subway

Make yourself at home in this beautifully renovated, family friendly house. Centrally located and just steps from Coxwell Station, Downtown Toronto is a short subway ride away. Vibrant walkable area, minutes to great restaurants, pubs, shops, parks, local farmers markets, and Michael Garron Hospital. This home is full of charm and natural light, featuring a spacious kitchen, cozy gas fireplace and a sunroom that opens onto a patio. Unwind in the spa bathroom with a soothing soaker tub.

Top 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, 590 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 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, 198 reviews

Beautiful 1 Bedroom Yorkville Condo (IG-hotspot)

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 cozy suite features a queen bed with decorative pillows, accompanied by a vibrant red sofa. A TV is positioned on a black unit, while framed floral artwork adorns the walls. A desk and chair are also present, creating a functional workspace in the inviting space.
Guest suite in Riverdale
4.95 out of 5 average rating, 200 reviews

Charming Suite in the Riverdale area of Toronto

While staying in our charming suite, enjoy the comforts of home in our newly renovated space. Our basement suite is fully equipped with bed, bath and kitchenette and includes applicable linens. Enjoy breakfast with the use of our kitchenette including: bar fridge, kettle and a Kuerig coffee maker. Snuggle up after a full day of exploring in our comfortable queen bed. Enjoy the comforts of home while in the heart of the city. Mi Casa es su Casa!

Top guest favourite
The exterior of a detached heritage home is showcased, featuring a brick façade and large windows. The entrance is framed by vibrant orange flowers and lush greenery. A yellow awning extends over the front door, adding a cheerful touch to the welcoming ambiance.
Home in Church-Wellesley
4.92 out of 5 average rating, 138 reviews

Heritage House all to Yourself! 1BR 3BA 2 Liv Rms

Beautiful detached heritage home on tree lined street in downtown Toronto. Wellesley Subway half block away. 1 bedroom w/ensuite, formal dining room, living room, kitchen w/breakfast room, separate TV room, and about a gajillion books to read :) We also have no hidden cleaning fees (don’t you hate those??) and our house keeper takes care of sheets, towels, garbage, cleaning etc when you leave.

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
4.82 out of 5 average rating, 104 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.

Top guest favourite
A modern living area features a light grey sofa adorned with decorative pillows, complemented by a circular area rug. Floor-to-ceiling windows allow natural light to fill the space, while green plants add a touch of nature. A sleek entertainment unit and a small dining table enhance functionality.
Apartment in Entertainment District
4.99 out of 5 average rating, 103 reviews

Bright & Stylish 1 Bedroom Condo in King West

My condo is at the heart of Toronto’s Entertainment/Fashion Districts and has everything you need for fantastic stay. The city’s trendiest restaurants and bars, theatres and sporting venues are steps away. Whether enjoying a short vacation or staying for an extended time, you’ll have all the comforts of home and access to the best Toronto has to offer. Welcome!

Top guest favourite
A modern living area features a spacious gray sectional sofa adorned with colorful throw pillows. Abstract artwork is displayed on the walls, while a round coffee table holds snacks. A large window allows natural light to fill the room, with a view of greenery outside.
Home in Annex
5 out of 5 average rating, 220 reviews

Annex Garden Coach House

Welcome to the Annex Garden Coach House! Well suited for solo and family travellers alike, seeking a centrally located, quiet little house, surrounded by backyard trees, in the leafy Annex neighbourhood. You're able to park for free at your private front door, and it's a quick walk to your choice of three nearby subway stations.

Popular amenities for Rosedale family-friendly rentals

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Quick stats about holiday rentals that are family-friendly in Rosedale

  • Total holiday rentals

    Explore 50 holiday rentals in Rosedale

  • Nightly prices starting at

    Rosedale holiday rentals start at £52 per night before taxes and fees

  • Verified guest reviews

    Over 1,650 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Rosedale holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Rosedale rentals

  • 4.9 Average rating

    Rosedale stays are highly rated by guests – averaging 4.9 out of 5!

  • Nearby attractions

    Rosedale’s top spots include Evergreen Brick Works, Bloor–Yonge Station and Bay Station

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