Family-friendly holiday rentals in York

4.95 out of 5 average rating, 115 reviews

Guest suite in York

Spacious suite with 8 foot ceilings.

Spacious and clean suite. Short walk to Eglinton Crosstown LRT. Near bus routes south to Keele, Ossington and Dundas West stations. Easy travel to north to Humber River Hospital, York University and Yorkdale Shopping Mall. Close to cafés, restaurants and shopping options. Eleven kilometers from Pearson airport. Note: My Airbnb is not downtown in the city centre. Please take note of the area in proximity to tourist attractions, so you can plan accordingly. Registration number: STR-2312-GSGRVT

5.0 out of 5 average rating, 23 reviews

Cottage in Toronto

The Cottage in High Park - free Parking

Escape to our city oasis! Nestled in High Park/Bloor West Village, our charming cottage offers urban tranquility just 15 mins from downtown by subway. Ride a bike to the beach, wander the tree-lined streets, explore boutiques in the local village, or forest-bathe deep in the trails of High Park. Return to cozy comfort, a wood-burning fireplace, a game of charades, or step out to a covered patio, perfect for BBQ creations or a movie under the stars. Your urban-cottage escape begins here!

4.95 out of 5 average rating, 254 reviews

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

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.

Guest suite in Junction Triangle

A modern kitchen features sleek white cabinetry and a countertop with a subtle texture. Essential appliances include a stove with four burners, a coffee maker, and a small kitchen rug adds warmth. Light is provided by recessed lighting throughout the space.

Bright west end 1-bedroom basement suite

A beautiful newly renovated basement suite, with 8ft ceilings, large windows, a glass rainfall shower & 2 comfy Queen sized beds (one is a fold-out sofa bed in the main living space). It's conveniently located close to the UP Express & TTC stations for traveling around the city. The house upstairs has a small child & there will be a certain amount of noise :) Please message me with any questions & I would be happy to answer you. Thanks for stopping by! registration # STR-2207-GGZRVF

4.94 out of 5 average rating, 157 reviews

4.99 out of 5 average rating, 96 reviews

Guest suite in York

Luxurious, spacious 9ft height Guest suiteToronto

Enjoy our brand-new, modern, and private suite in a quiet yet convenient neighbourhood. It is ideal for romantic getaways, family vacations, or the business travellers seeking a refined alternative to a hotel. Easily accessible by car or public transit, you’re close to Toronto’s vibrant areas such as The Junction, Bloor West Village, downtown, and the CN Tower. Conveniently located just minutes from Pearson Airport, the Toronto Congress Centre, and the Metro Toronto Convention Centre!

4.99 out of 5 average rating, 214 reviews

A modern living area features a sleek brown leather couch with decorative pillows, positioned across from a dark wooden coffee table. Bright natural light enters through large bay windows, complemented by light-filtering curtains. A decorative wall map and a large green plant add character to the space.

Home in York

Welcome to Greenhills, a Charming Home w/ Parking

Clean Open Concept, Sun-Filled 2 Bedroom main floor home with PARKING; Can sleep up to 4 people. Featuring simple modern décor, queen size beds, big beautiful windows with room darkening curtains, closet storage. Dedicated office desks in bedrooms Full kitchen, with oil, seasoning spices, toaster, hot water kettle, Keurig Coffee Machine and complimentary coffee+tea. Clean bathroom with shampoo+conditioner+body wash+lotion SMART TV 60” Fast internet Wifi Check-In: 3PM Check-Out: 11AM

4.88 out of 5 average rating, 116 reviews

Guest suite in Toronto

Spacious High Park Studio

Experience the best of Toronto, High Park, Bloor West Village, and the Junction in this spacious room. Walk 5min to subway and 10min to High Park. This 850 square foot studio includes a King size bed with additional flexible sleeping options (air mattress and infant pack 'n play as required). Enjoy your stay in comfort with complete control of the temperature in space with a dedicated thermostat and supplemental AC/Heating. Entertainment Included: WiFi, Netflix, Apple TV, Disney+ etc.

4.92 out of 5 average rating, 142 reviews

An open-concept living area features a light-colored sofa and a chic coffee table, complemented by a neutral rug. A staircase leads to the upper floor, while a dining area is visible in the background near large windows allowing natural light.

Home in Islington

Luxury Home - 5 min from airport, 15 to downtown

The stunning house in Etobicoke is only a few minutes from the Airport and City Centre. This spacious open concept, rare luxury modern home, is beautifully designed and decorated. It is a fully stocked home and will have everything you could ever wish for a short-term stay. Perfect for large families and groups! min age 25 yrs to book. Room 1 king bed Room 2 queen Room 3 twin and another twin roll out Room 4 queen no party policy or excessive noise. this is a quiet listing

4.91 out of 5 average rating, 122 reviews

A cozy living space features a blue sofa with patterned cushions and a wooden coffee table. A round mirror hangs on the wall, reflecting natural light. A floor lamp provides additional lighting, and a small chair is positioned nearby. A plant adds a touch of greenery.

Home in Midtown

Spacious Mid Century w/Patio

Adorable Historic Home with Private Patio & BBQ. ♡ 3 bedroom & 1.5 bath (1 King & 2 Queens) ♡ Hotel Inspired Home with Super Fast WIFI ♡ Automated Check in & Check Out ♡ Steps from St. Clair transit line / connects to Subway ♡ 90/100 Walk Score ♡ 100/100 Transit Score ♡ Walking distance to Casa Loma | Rated #1 by BlogTO of Places to Visit in Toronto ♡ Flexible Check in Check out - Message for Details ♡ A/C ♡ Laundry ♡ BBQ & Fully Equipped Kitchen ❤ Book today!

5.0 out of 5 average rating, 109 reviews

A bright living area is furnished with a light-colored sofa and a pair of wooden side tables. A textured area rug covers the hardwood floor, while natural light is allowed in through a nearby window. A small desk and chair are positioned against the wall.

Home in Toronto

Cozy and Modern Lower-Level Suite in Corso Italia

Welcome to your home away from home! This newly updated, bright and cozy suite is nestled in Toronto’s buzzing Corso Italia neighbourhood. This apartment offers the perfect blend of comfort, privacy, and convenience. Whether you're here for a short stay or a longer getaway, you'll enjoy a comfortable retreat in this recently renovated and thoughtfully designed space. You will have access to the entire apartment accessible via a separate entrance located in the backyard.

4.91 out of 5 average rating, 227 reviews

A cozy interior scene showcases a modern studio space. A vase with greenery and purple flowers sits on a wooden side table. The spacious bed is adorned with neutral-colored pillows, adding to the room's calm aesthetic. A framed image of a stag is featured on the wall behind.

Apartment in York

Cozy Junction Studio | Walk to Cafés & Transit

Modern newly renovated studio for 2 in Toronto’s vibrant Junction neighborhood. Clean, bright, and comfortable space with fast Wi-Fi and easy self check-in. Located in a walkable area surrounded by great cafés, restaurants, and grocery stores, all just minutes away. Public transportation nearby makes it easy to reach downtown Toronto and High Park. Perfect for couples or travelers looking for a convenient, comfortable stay in one of Toronto’s most lively neighborhoods.

4.9 out of 5 average rating, 199 reviews

Apartment in Toronto

Spacious & Vibrant

Stay comfortably in this spacious 2-apartment in vibrant Corso Italia, perfect for couples, friends or small groups of friends. Enjoy a bright and private second-floor unit with plenty of space to relax after exploring Toronto. Step outside to enjoy your private patio, or take advantage of convenient parking. With transit just steps away, you’ll have easy access to downtown, Toronto’s attractions, restaurants, and entertainment. Parking included.

Popular amenities for York family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guesthouse in Mississauga

A serene backyard is highlighted by a clear swimming pool surrounded by natural stone coping. Comfortable seating arrangements with dark wicker chairs and a sleek table are positioned nearby, offering a relaxing spot. Lush greenery frames the area, providing a peaceful atmosphere.

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

4.89 out of 5 average rating, 114 reviews

4.99 out of 5 average rating, 187 reviews

The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.

Home in The Beaches

Luxury 4BR: 365 Days Open- Heated Pool & Hot Tub

4.92 out of 5 average rating, 114 reviews

Home in Toronto

Backyard Oasis | Hot Tub & Playground | Near DT

5.0 out of 5 average rating, 161 reviews

A bright and airy living space features large corner windows that offer expansive views of the city. A modern sectional couch is paired with a light rug, while a flat-screen television is mounted on the wall. Lush green plants add a touch of nature to the inviting décor.

Condo in Yorkdale

The Penty: Luxurious Penthouse with Pool, Hot Tub

Condo in Downtown Toronto

A comfortable living area is presented with a light-colored sectional sofa and a brown leather armchair. A modern entertainment unit displays a flat-screen television, complemented by framed artwork on the walls. A soft area rug partially covers the wooden floor, enhancing the inviting atmosphere.

Luxury Downtown Condo For 4 (CN Tower Views)

4.94 out of 5 average rating, 124 reviews

4.98 out of 5 average rating, 105 reviews

An outdoor deck area features a hot tub beside a modern stainless steel barbecue grill. The warm wooden flooring is complemented by surrounding greenery, providing a natural setting for relaxation and outdoor cooking.

Home in East York

Hot Tub + Trampoline | Fun Backyard Escape

4.85 out of 5 average rating, 110 reviews

A private outdoor space features a hot tub positioned beside a blue swimming pool. Surrounding amenities include a charcoal grill, dining table, and lounge chairs set on a wooden deck, with trees providing natural shade and decorative lighting enhancing the evening atmosphere.

Home in Toronto

Toronto Pool Retreat

4.92 out of 5 average rating, 122 reviews

A bright sunroom is showcased with a glass ceiling and walls, providing expansive views of the surrounding nature. A glass dining table is surrounded by black chairs, resting on a soft area rug. The space offers a connection to the outdoors while remaining sheltered.

Home in Scarborough

Ravine Paradise ! heated pool and hot tub!

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 152 reviews

Home in Roncesvalles

Garden Gem | Central | Walk to City's Best Places.

4.98 out of 5 average rating, 194 reviews

Place to stay in Midtown

A spectacular and authentic loft!

4.99 out of 5 average rating, 110 reviews

A modern kitchen with sleek cabinetry features a spacious island with seating for four. Large windows provide natural light and a view of the outdoors, while elegant pendant lights hang above. The adjacent living area showcases a comfortable sofa and a coffee table on a light-colored rug.

Home in Parkdale

Luxury home with 4 king suites near High Park

4.98 out of 5 average rating, 107 reviews

A spacious outdoor deck is furnished with a large sectional couch and a glass table. The well-maintained garden is bordered by wooden fencing, featuring a lush green lawn, flowering plants, and a hammock hung between two trees, with a children's playhouse visible in the background.

Apartment in Midtown

Main fl Annex, private garden oasis, welcome dogs!

5.0 out of 5 average rating, 101 reviews

A spacious living room is highlighted by a charcoal gray sofa and a light beige armchair, positioned around a soft area rug. Built-in bookshelves frame the room, filled with books and decorative items. Natural light floods in through multiple windows, creating an inviting atmosphere.

Home in Midtown

Designer 4 bedroom house - Ossington Station

Bungalow in Mimico-Queensway

The cozy living room features a genuine leather sofa and a love seat, complemented by a round coffee table. Soft lighting from two lamps enhances the space, while a window covered with light shades allows natural light to filter through. A small dining table is set near the window.

Super Cozy Home in Toronto - Just 2 stops to Union

4.97 out of 5 average rating, 180 reviews

Luxe

A modern living room features a gray sofa with decorative cushions, a coffee table, and a cozy rug. Shelves against the wall display books and decorative items, with a warm wooden accent above. A plant and stylish lighting enhance the inviting atmosphere.

Home in Downtown Toronto

The Robert House: Masterpiece in Harbord Village

4.93 out of 5 average rating, 136 reviews

Loft in Junction Triangle

A bright corner of the living area showcases a spacious sectional couch with decorative pillows, accompanied by a cozy throw. A large abstract painting adorns the wall, featuring vibrant colors. Natural light filters through large windows, highlighting indoor plants and a soft-textured rug.

Large Artsy Loft w 30ft Ceilings and Natural Light

4.96 out of 5 average rating, 125 reviews

Family-friendly home rentals with a pool

4.84 out of 5 average rating, 134 reviews

A spacious living room is presented with a neutral-colored sectional sofa adorned with yellow accent pillows. A small glass side table complements the seating area, while a patterned area rug adds texture to the floor. Natural light enters through a window placed above the sofa.

Apartment in York

Bright, spacious luxury basement apartment

4.94 out of 5 average rating, 104 reviews

A welcoming entryway features a stone staircase leading to a pair of wooden double doors. Flanking the entrance, potted plants add greenery, while large windows provide views of the surrounding yard. The roof is tiled, and a well-maintained lawn adds to the home's appeal.

Place to stay in Toronto

The Snug Oasis - Burrow (Near Airport)

4.92 out of 5 average rating, 218 reviews

The indoor swimming pool area features a tiled pool surrounded by natural light from large skylights. Two colorful floats are positioned on the water surface, and glass doors provide a view of the outdoors, enhancing the open and airy feel of the space.

Villa in Toronto

Toronto Vacation | ➊ The One Toronto Villa

Apartment in Downtown Toronto

Stunning Skyline View Condo, Steps to CN Tower

4.93 out of 5 average rating, 160 reviews

4.96 out of 5 average rating, 121 reviews

Home in Erin Mills

Luxurious 2 bdr suite near SQ1, UTM, parking/pool

4.9 out of 5 average rating, 167 reviews

A modern condominium building is showcased from a street view, highlighting two tall, sleek towers with an expansive glass façade. The ground level features a multi-story section with large windows and contemporary architectural elements, set against a clear blue sky.

Condo in Mississauga

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

Condo in Downtown Toronto

A modern living area is highlighted by large windows offering views of the outside. A spacious sectional sofa is complemented by decorative cushions. A sleek kitchen island with stone countertops provides ample space, and a dining area is visible, accented by natural light.

3BR Penthouse with Panoramic Views + Large Terrace

4.89 out of 5 average rating, 115 reviews