Family-friendly vacation 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 favorite
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 Midtown
4.97 out of 5 average rating, 124 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 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
4.9 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 favorite
A cozy living room is presented with a large floral artwork adorning one wall. A comfortable sofa with decorative cushions faces a television, while a wooden coffee table is positioned in the center. Light filters softly through the lace curtains, illuminating the space.
Home in Downtown Toronto
4.94 out of 5 average rating, 129 reviews

Artist's Lovely Cabbagetown Century Home Downtown

Located in a peaceful historic neighbourhood, you'll feel right at home in this Arts and Crafts residence featuring authentic finishes, hardwood floors, private courtyard garden, and deck. A quaint cottage-like gem filled with the artist's original works. Fast hi-speed Wi-Fi, premium cable. One block from streetcars. Many award-winning restaurants, jazz bars and gourmet shops. Walking distance to the core of Toronto's downtown. Street parking and city lot on the block. Superhost for 11 years.

Guest favorite
An open living space is visible, featuring light-colored walls and wooden flooring. A large moose head mount decorates the wall, adding a unique focal point. Two barstools are positioned at a kitchen counter, with kitchen appliances discreetly arranged in the background.
Condo in Downtown Toronto
4.96 out of 5 average rating, 166 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.

Top guest favorite
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 favorite
Home in Downtown Toronto
4.99 out of 5 average rating, 250 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

Top guest favorite
A spacious living area features a dark gray sectional sofa and a wooden coffee table adorned with decorative items. Natural light illuminates the space, highlighting a gas fireplace underneath the wall-mounted television. A dining area with four chairs is visible in the background.
Home in Toronto
4.99 out of 5 average rating, 116 reviews

New! Private 1BR in Toronto by Danforth, Sleeps 4

Welcome to our stunning, newly renovated home in Toronto’s Old East York neighborhood, just a two minute walk from trendy Danforth Avenue and Pape Subway Station. This bright and airy, coastal-inspired retreat blends the comfort of home with the soothing simplicity of Maritime charm. This private oasis spans 750 square feet and is ideal for those seeking a peaceful escape in East York, with easy access to the best of Toronto. We'd put our accommodations up against the hotels of Toronto!!!

Top guest favorite
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 Downtown Toronto
4.93 out of 5 average rating, 148 reviews

Entire Heritage House for Two! 1BR 3BA 2 Liv Rms

Beautiful detached heritage home on a quiet, tree-lined street in the heart of downtown Toronto. Wellesley Subway Station is just half a block. We offer one spacious bedroom with ensuite bathroom, formal dining room, living room, modern kitchen with bright breakfast area, and tv room. You’ll also find an extensive library throughout the home — perfect for curling up with a book during your stay. Our pricing is transparent, with a modest cleaning fee and no surprises at checkout :)

Top guest favorite
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, 113 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 favorite
A bright bedroom features a spacious bed adorned with plush pillows in pink stripes. Large windows provide stunning views of the cityscape, while dark curtains offer options for privacy and light control.
Condo in Yorkville
4.99 out of 5 average rating, 196 reviews

Admire City Views from Bed at this Chic Apartment

The critics have spoken! This five-star rated, professionally designed unit offers a fresh, functional, and beautifully curated living experience. Every piece of artwork and each accessory has been thoughtfully selected to enhance comfort, style, and positive energy throughout the space. This spacious one-bedroom, one-bathroom suite features a fully equipped kitchen, open living and dining areas, and a versatile den — perfect for working remotely or relaxing after a day in the city.

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 Downtown Toronto
4.94 out of 5 average rating, 188 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.

Guest favorite
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, 209 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.

Popular amenities for Rosedale family-friendly rentals

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

  • Total vacation rentals

    Explore 50 vacation rentals in Rosedale

  • Nightly prices starting at

    Rosedale vacation rentals start at ﺩ.ﺇ 257 per night before taxes and fees

  • Verified guest reviews

    Over 1,710 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Rosedale vacation rentals include wi-fi 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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