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.

%{current} / %{total}1 / 1
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, 117 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.

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, 313 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 comfortable living area is depicted with a taupe sofa and an accent chair near a wooden coffee table. The space is softly lit, highlighting a striking artwork on the wall. A light-colored area rug rests beneath the coffee table, adding texture to the cozy setting.
Home in Upper Beaches
4.98 out of 5 average rating, 194 reviews

Large & Loungy Private 2 Bedroom - Private Suite

Private Suite Separate Entrance. Large Loungy Private 2 bedrooms, living room, kitchen with hot plate fridge, dining area, bathroom, laundry room, EXCLUSIVE FOR GUESTS ONLY NO SHARED SPACES. A newly renovated and beautiful space. Luxurious linens and extra soft towels, dining and living room are open concept, and are available exclusively for guests - no shared spaces. Coffee - Tea bar area, books, magazines & board games. Full size washer & dryer. Free Private Parking in driveway. EV charger

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, 588 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.
Flat in Cabbagetown
4.94 out of 5 average rating, 162 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 favourite
The living area features a modern design with a comfortable sofa accented by patterned pillows. A marble dining table is surrounded by elegant chairs. A striking chandelier hangs above, while a large round mirror reflects the ambient light from windows dressed in soft curtains.
Home in Corktown
4.99 out of 5 average rating, 238 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.”

Top guest favourite
The open-space living area features a large leather sofa facing a flat-screen TV, with a dining table and chairs nearby. A modern kitchen with high-end appliances is visible in the background, complemented by bright, recessed lighting throughout the space.
Flat in Davisville Village
4.95 out of 5 average rating, 157 reviews

Midtown modern 1 bedroom suite

Located in the heart of Midtown, Davisville Village. Very close to public transit, grocery stores and trendy restaurants. New property, modern look, high-end new appliances (incl. washer & dryer), modern comfortable furniture. Highest standards of cleaning, including proper disinfection of all high-touch areas. All kitchen, bathroom and bedroom supplies for comfortable stay provided. On-site parking is available for a separate fee. High-speed Wi-Fi access, Netflix, cable TV.

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
4.94 out of 5 average rating, 195 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
A cozy bedroom is presented with a spacious bed featuring a light-colored quilt and neatly arranged pillows. A modern bedside lamp illuminates one side, while natural light enters through two windows. A private entrance door is adjacent to the bed.
Flat in Riverdale
4.91 out of 5 average rating, 125 reviews

Spacious Riverdale One Bedroom Garden Suite

This freshly renovated garden suite has everything you need while you enjoy your time in Toronto. Bright and stylishly designed in a classic Toronto Edwardian. The street car is just a few minutes away for a short ride to downtown or the subway. Our guest suite offers a full kitchen, washer and dryer, luxurious bed linens, a Casper queen bed, and a pullout sofa. The private entrance is just five steps down from the shared patio and garden.

Top guest favourite
A spacious room is displayed with a comfortable queen bed positioned against the wall, accompanied by two bedside lamps. A soft sofa and a green accent chair create a cozy sitting area, while framed artworks and a large window provide a bright, airy ambiance.
Guest suite in York
5 out of 5 average rating, 144 reviews

Private, Spacious,Separate Entrance, Bath, Parking

My Airbnb is located in a green and safe valley between one of the biggest Toronto parks and Bloor West Village/Junction just steps away from trendy cafes and shops. Our Airbnb has a separate entrance. Stunning biking trails are 2 min walk at Etienne Brule gate and lead to Lake Ontario passing Old Mill or north, James' Gardens. You can see salmon traveling upstream of the Humber River in the Fall.

Top guest favourite
A small balcony features a bistro table and two wooden chairs, overlooking a serene view of Lake Ontario. A potted plant sits in the center of the table, with the shimmering water and distant shore visible in the background.
Apartment in Harbourfront
4.97 out of 5 average rating, 314 reviews

Lively 1+1 Lakeview Condo near CN Tower + Free Prk

Enjoy the stunning lake view in this open concept 700 sq ft condo with 9 ft ceilings, in the heart of the harbourfront. Right next to CN Tower, Rogers Centre, and Scotiabank Arena. Includes parking space, TV, and internet. Gym, indoor-out door pool, Variety of restaurants and grocery stores steps away. Minutes walk to subway, Union Station, the business district, and Billy Bishop City Airport.

Guest favourite
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, 103 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.

Popular amenities for Rosedale family-friendly rentals

When is the best time to visit Rosedale?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price£130£134£134£160£148£182£182£183£182£182£179£139
Avg. temp-3°C-3°C2°C8°C14°C20°C23°C22°C18°C11°C5°C0°C

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 £53 per night before taxes and fees

  • Verified guest reviews

    Over 1,440 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 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

  1. Airbnb
  2. Canada
  3. Ontario
  4. Toronto
  5. Rosedale
  6. Family-friendly rentals