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.

4.94 out of 5 average rating, 163 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

KitchenIndoor spacesNearby

5.0 out of 5 average rating, 19 reviews

Apartment in Downsview

Charming Urban Escape!

Welcome to Your Charming 2-Bedroom Retreat in North York! Experience comfort and convenience in this beautifully appointed 2-bdrm home located on Powell Road. Just steps away from the brand-new Budweiser Stage, and minutes from popular destinations like Home Depot, Costco, and a variety of shops, restaurants, and everyday essentials. Whether you’re here for business or leisure, this cozy and stylish space offers everything you need for a relaxing stay in the city. 7 Years super host in a row!

FamilyIndoor spacesNearby

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.

Indoor spacesFamilyBathroom

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, 132 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.

KitchenIndoor spacesBathroom

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, 102 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.

Indoor spacesKitchenComfort

4.99 out of 5 average rating, 470 reviews

A dining table is elegantly set with two decorative plates, glasses of varying sizes, and utensils arranged symmetrically. A soft glow is provided by a small candle flickering in a metallic holder, creating a subtle ambiance for mealtime.

Guest suite in Vaughan

Quiet Vaughan Retreat near Wonderland & Hwy 400

Enjoy a stylish and peaceful stay at this centrally located one-bedroom lower-level unit, perfect for both leisure and business travelers. With your private entrance, parking, and all the essentials, it’s your ideal home away from home. Features include a full kitchen, bathroom, internet, smart TV, one Queen and one sofa bed, and a functional workspace. Steps from FreshCo, Walmart, restaurants, and services. Minutes to Vaughan Mills, Canada’s Wonderland, Cortellucci Hospital and transit.

Indoor spacesFamilyValue

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

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.

FamilyIndoor spacesAmenities

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

FamilyKitchenValue

4.98 out of 5 average rating, 223 reviews

Guest suite in Midtown

Bright Private Basement Suite | 1BR Near Subway

A newly renovated, private lower-level (basement) 1-bedroom, 1-bath suite located in Toronto’s Annex West, just a 3 minute walk to the subway and buses. Bright, quiet, and thoughtfully designed, this self-contained space is ideal for solo travelers, couples, or short business stays. Enjoy heated floors, unlimited hot water, fast Wi-Fi, a full kitchen, and comfortable living and dining areas—steps from restaurants, parks, shops, and beautiful residential streets.

FamilyIndoor spacesAccuracy

4.82 out of 5 average rating, 17 reviews

Modern 4BR Home • Walk to subway • Superhost

Bright and spacious home in a quiet North York neighborhood. Features open living and dining areas, a full kitchen, and 4 comfortable bedrooms. Includes Wi-Fi, A/C, laundry, and deck. Steps from Yonge Street, parks, shops, and less than a mile to Finch subway for easy access downtown. Perfect for families or groups seeking comfort and convenience in Toronto. Super host 7 years in a row we plan to offer you the same comfort we have provided guests over years.

FamilyIndoor spacesAmenities

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, 111 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!

KitchenFamilyCleanliness

5.0 out of 5 average rating, 27 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

KitchenIndoor spacesBathroom

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

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, 114 reviews

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

FamilyIndoor spacesNearby

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

FamilyKitchenValue

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

KitchenIndoor spacesSleep quality

4.86 out of 5 average rating, 147 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

KitchenFamilyWi-Fi

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

FamilyKitchenAccess

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, 125 reviews

Luxury Downtown Condo For 4 (CN Tower Views)

Indoor spacesKitchenWalkability

Condo in Davisville Village

A modern living space features a spacious seating area with a gray sofa and a bright orange accent chair. A dining table with plants stands nearby. Natural light floods the room through a glass sliding door leading to a balcony, offering views of the city skyline.

4.84 out of 5 average rating, 160 reviews

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins

KitchenFamilyNearby

4.92 out of 5 average rating, 114 reviews

Backyard Oasis | Hot Tub & Playground | Near DT

KitchenFamilyParking

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

KitchenIndoor spacesHospitality

4.93 out of 5 average rating, 195 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

Indoor spacesFamilyLayout

4.9 out of 5 average rating, 285 reviews

A living room features a gray sofa accented with decorative cushions, paired with two mid-century modern chairs. A large window allows natural light to illuminate the space. A mounted flat-screen TV and an electric fireplace are visible, enhancing the cozy atmosphere.

Guest suite in Toronto

Midtown Luxury Yonge/Lawrence Close to Downtown

Indoor spacesKitchenQuiet

4.98 out of 5 average rating, 360 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

KitchenFamilySleep quality

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!

KitchenIndoor spacesAmenities

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

FamilyIndoor spacesAmenities

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

FamilyKitchenNearby

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

KitchenFamilyCondition

Family-friendly home rentals with a pool

Apartment in Downtown Toronto

4.93 out of 5 average rating, 160 reviews

Stunning Skyline View Condo, Steps to CN Tower

Indoor spacesFamilyView

4.97 out of 5 average rating, 120 reviews

The entrance features a wide stone staircase leading to double wooden doors with intricate designs. Potted plants add greenery on either side, while a pathway is lined with grass and nearby trees. The home's facade showcases classic stonework and a tiled roof.

Place to stay in Toronto

The Snug Oasis - Woodstock (Near Airport)

FamilyKitchenWalkability

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!

Indoor spacesFamilyWi-Fi

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

Indoor spacesKitchenPool

4.82 out of 5 average rating, 121 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

KitchenFamilyView

Condo in Downtown Toronto

A rooftop pool reflects the blue sky while providing views of the CN Tower and surrounding modern buildings. Lounge chairs are positioned beside the pool, creating a relaxed atmosphere. The clear water invites enjoyment against the urban backdrop.

4.94 out of 5 average rating, 178 reviews

Rooftop Pool Condo with CN Tower View

FamilyIndoor spacesAir conditioning

4.94 out of 5 average rating, 194 reviews

A modern living area features a large window with expansive views of the cityscape and surrounding landscape. A flat-screen television is mounted on the wall opposite a comfortable sofa and a coffee table, creating a welcoming space for relaxation.

Apartment in Mississauga

Luxury Stay w/phenomenal view!

Indoor spacesKitchenTV