Family-friendly holiday rentals in North York

Guest suite in Richmond Hill

A spacious living area features a light-colored sectional sofa and an upholstered chair positioned around a glass coffee table. A soft area rug lays beneath, while neutral walls and recessed lighting contribute to a bright atmosphere. A staircase is visible in the background.

4.95 out of 5 average rating, 165 reviews

Luxurious Retreat ; 2BR basement

Welcome to our modern brand new 2BR, 2BA basement in Richmond Hill! Ideal for families or groups, it boasts a stylish living space, laundry area, and well-equipped kitchenette. The master bedroom features a fireplace and attached bathroom, while both bedrooms offer king-size beds and ample storage.Entertainment is provided with a TV and Wi-Fi-Netflix and Amazon prime,in a luxurious neighborhood, just a 5-minute walk to Yonge St and bus station for easy access . Experience comfort and convenience

Home in Davisville Village

A spacious living area is highlighted by a green sofa with decorative cushions, positioned near large glass doors that lead to a private backyard. Natural light fills the space, complemented by contemporary wall art and indoor plants, creating a relaxed and inviting atmosphere.

4.96 out of 5 average rating, 157 reviews

Family Oasis • Near Subway • Free Parking

BEST MIDTOWN LOCATION AND AMPLE SPACE - ALL TO YOURSELF! FREE 2-CAR PARKING - rare in this area. You’ll be close to everything at this centrally located midtown place steps away from Yonge str. Charming and spacious renovated character home. Sun-drenched family room overlooks a private backyard with a patio. Walking distance to public transit and major streets with 24h shopping and fine dining. 10 minutes to downtown by driving, steps to subway and minutes to top-rated attractions in Toronto!

A modern living area features sleek black sofas accompanied by decorative pillows. A light marble coffee table sits between them. Large windows provide natural light and a view of the outdoors, while a wall-mounted television is visible in the kitchen space.

4.9 out of 5 average rating, 111 reviews

*New* Modern Home Toronto, 5-min walk to Metro

Step into this modern 2-bed 2.5-bath house for your next cozy yet luxe home away from home! You’ll be located in up-town Toronto. You’re one train away from the CN Tower and the downtown core. You'll be situated close to Pearson Airport, shopping malls, stores, and an array of trendy restaurants. The home is equipped for all your needs, including a full kitchen with all the right appliances, high-speed Wi-Fi, and free parking. My goal is for you to feel at home - when you’re away from home.

A spacious living area features a comfortable sectional sofa and a coffee table situated on a patterned rug. A large television is mounted on the wall, while natural light floods in through the windows, which offer views of the backyard and patio.

4.95 out of 5 average rating, 133 reviews

Beautiful Modern Home, Heart of Bayview Village

Stay with confidence at a 6-year Airbnb Superhost home known for exceptional cleanliness and care. This bright 3-bedroom, 2-bath unit offers far more space than a typical hotel or condo, plus a private backyard, a rare city retreat to relax, enjoy a morning coffee, or unwind after a day out. Located minutes from Bayview Village, it features up to 2 dedicated parking spots, a comfortable layout, private bedrooms, and inviting living areas, ideal for families, professionals, and longer stays.

A bright living room is highlighted by large windows covered with shutters, allowing natural light to fill the space. A modern chandelier suspends from the ceiling, and a flat-screen TV is mounted on a stone wall. Comfortable seating includes a blue sofa and two yellow chairs, surrounding a glass coffee table.

4.92 out of 5 average rating, 103 reviews

Urban Haven | Entire Main floor | Indoor Parking

"Elysian Urban Haven" is a luxurious residence designed to cater to various categories of travelers, promising an extraordinary experience in the heart of midtown Toronto. This exquisite residence features three bedrooms, two washrooms, and a full kitchen, equipped with top-of-the-line appliances, ceramic countertops. The location is truly a gem with easy access to major highways and downtown. Whether guests plan to explore the city or attend important meetings, this ensures convenience.

4.93 out of 5 average rating, 196 reviews

The spacious living area features a light-colored sectional sofa arranged around a circular coffee table. A large Smart TV is mounted on the wall, while abstract artwork adorns the walls. Natural light enters through double doors leading to the patio, complemented by a decorative plant.

Home in Markham

2BR+2Bath! 2queen beds! Luxury Private Quiet Clean

Fully renovated, modern, Bright, luxurious, and spacious ( over 1800 sq/ft) 2-bedroom, 2-bathroom high ceiling above ground apartment, separate entrance, and Patio for your next cozy home away from home! 5-star rated and top 5% of homes in AirBnB! As central as it gets in the GTA. You'll be close to Pearson Airport, Highway 401/404/407, shopping malls, grocery stores, and an array of trendy restaurants, movie theaters, parks, and bicycle/ hiking trails all around Book With Confidence!

4.99 out of 5 average rating, 215 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

4.92 out of 5 average rating, 219 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

The One is a unique luxurious private midle-century modern villa escape in the center of north Toronto. Having a stunning and spacious lawn for events and social gathering, this modern house is featured a thermostatic indoor swimming pool. Being inspired from a farmhouse building, the house offering a traditional touch on the vintage furniture and a rustic interior that gives a warm and cozy feelings. It is a great escape from the hustle and bustle of city life without going out of town.

4.92 out of 5 average rating, 144 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

4.93 out of 5 average rating, 41 reviews

Townhouse in Toronto

Modern 3BR Townhome | 3 Ensuites | near Subway

Welcome to this modern and spacious 3-bedroom townhouse in North York, Toronto! Each bedroom features its own private ensuite bathroom, offering comfort and privacy for families, groups, or business travelers. Enjoy a fully equipped kitchen, bright living spaces, and the convenience of 2 parking spaces. Located just a short walk from Finch Subway Station, with easy access to downtown Toronto, restaurants, shopping, and daily essentials. **We warmly welcome well-behaved pets.**

Guesthouse in Richmond Hill

The exterior of a newly constructed coach house is showcased, featuring a modern design with stone and brick elements. Two garage doors are visible, along with a front porch and balcony above. A well-maintained lawn and a young tree add greenery to the inviting entrance.

4.94 out of 5 average rating, 113 reviews

Entire 1 Bedroom Detached Coach House

This completely private and newly built (Dec 2023) independent one bedroom coach house is located in the prestigious Observatory Hill neighborhood in south Richmond Hill. Convenient location near transit, shops and restaurants (mins drive to Hwy 404 and Hwy 407). This unit also offers secure internet, Keurig coffee machine, TV, independent AC, furnace, laundry, private entrance with easy Smart Lock access and two free parking on the driveway and many more!

5.0 out of 5 average rating, 28 reviews

Guest suite in Toronto

Luxury Private 1BR Suite l Toronto

A custom home built in 2025. This is a completely furnished 1-bedroom suite with a bathroom, a private laundry, free parking, and amenities at the heart of North York (Yonge and Sheppard) Enjoy your Toronto stay at our suite. - 2 minutes walk to Yonge-Sheppard Subway station - 2 minutes walk to restaurants and shopping - 20 minutes from Pearson airport - Approx. 6 km to Rogers Stadium - Subway to Rogers Centre - EV Charger available upon request

Popular amenities for North York family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

5.0 out of 5 average rating, 163 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

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.

4.89 out of 5 average rating, 116 reviews

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

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

4.87 out of 5 average rating, 149 reviews

The geodesic dome features a modern white exterior, set against a backdrop of trees. A wooden deck extends from the dome, leading to a covered gazebo, with a pathway of wood chips guiding the approach. Soft sunlight filters through the branches, creating a serene atmosphere.

Dome in Uxbridge

The Bubble Glamping Dome

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.

4.85 out of 5 average rating, 110 reviews

Toronto Pool Retreat

4.9 out of 5 average rating, 168 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

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

4.92 out of 5 average rating, 115 reviews

Backyard Oasis | Hot Tub & Playground | Near DT

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 522 reviews

A kitchenette area features modern cabinetry and countertop space, illuminated by recessed lighting. Decorative touches, including wall art and greenery, create a welcoming atmosphere. Appliances include a full fridge and microwave, with options for cooking, providing convenience for guests.

Home in Vaughan

Private Lower 1 BR + Sofabed Self Checkin with PKG

4.96 out of 5 average rating, 106 reviews

The living area features a blue sofa bed positioned across from a modern media unit. A coffee table is centered in front, and sunlight filters through large windows with sheer curtains. A dining area is visible in the background, accompanied by potted plants.

Apartment in Scarborough

Just like home

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!

4.98 out of 5 average rating, 362 reviews

A spacious living area features a variety of seating options, including a cozy couch and rocking chairs. Large windows allow natural light to enter, illuminating the lush indoor plants. Decorative rugs and artwork add character to the eclectic decor, creating a relaxed atmosphere.

Farm stay in Uxbridge

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

4.91 out of 5 average rating, 124 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

Guest suite in Richmond Hill

The living area is furnished with light-colored sofas arranged around a glass coffee table, creating an inviting space for relaxation. Soft lighting from recessed fixtures complements natural light filtering through windows. A modern fireplace provides warmth, while decorative plants enhance the overall ambiance.

4.97 out of 5 average rating, 115 reviews

Snow-Free Garage Parking / Modern bright 2BR Suite

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

4.93 out of 5 average rating, 136 reviews

The Robert House: Masterpiece in Harbord Village

Bungalow in Richmond Hill

The exterior of a bungalow is depicted, featuring a wooden deck with a sun motif and vibrant flower beds. Lush green grass is visible in the foreground, while a wooden fence provides privacy along one side. A clear blue sky with scattered clouds enhances the outdoor setting.

4.83 out of 5 average rating, 206 reviews

BRANDNEW BASEMENT 2BEDROOM 2BATHROOM FULLY LOADED

Family-friendly home rentals with a pool

4.94 out of 5 average rating, 106 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)

Apartment in Downtown Toronto

4.92 out of 5 average rating, 162 reviews

Stunning Skyline View Condo, Steps to CN Tower

Guest suite in Scarborough

A spacious backyard features a large swimming pool surrounded by lush greenery. An umbrella provides shade to a seating area, while trees encircle the space, enhancing privacy. A fenced perimeter ensures safety, and the pool is inviting under dappled sunlight.

4.89 out of 5 average rating, 114 reviews

1BR Bluffs | Pool + Yard | Pets Ok | EV Charger

4.82 out of 5 average rating, 122 reviews

A spacious living area is featured, with large windows offering natural light and views of the city. A comfortable gray sofa is situated alongside a vibrant red armchair. A wooden coffee table rests on a patterned rug, complemented by a flat-screen TV and decorative artwork.

Condo in Etobicoke

Humber Bay Family Friendly condo w Terrace&Parking

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.

4.94 out of 5 average rating, 126 reviews

Luxury Downtown Condo For 4 (CN Tower Views)

Guest suite in Scarborough

A modern outdoor space features a large in-ground pool with vibrant blue water. An elegant fire pit sits in the foreground, its flames flickering above reflective glass stones. Surrounding the pool, tall wooden fences provide privacy, complemented by outdoor chairs positioned nearby.

4.9 out of 5 average rating, 145 reviews

New Custom-Built | Marble Pool + BBQ | Toronto

Apartment in Downtown Toronto

A round marble dining table is featured in the center, surrounded by wooden chairs. Above hangs a stylish light fixture. A decorative hockey-themed wall art is displayed, reflecting local culture. The open kitchen area includes modern appliances and a neutral color scheme, enhancing the inviting space.

4.92 out of 5 average rating, 182 reviews

Canadiana Downtown Condo w/King Bed + Free Parking