Family-friendly holiday rentals 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, 141 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

4.97 out of 5 average rating, 192 reviews

Home in Richmond Hill

Place You Want To Stay at With Tons of Options ! !

Brand New, Modern & Open Concept Basement Unit With 9 ft Ceilings & Brand New LG Appliances, Located at Bathurst & King Street In Richmond Hill. Beautifully Decorated & Fully Furnished For Your convenience, Making it a Comfortable Stay - Min walk to Community Park With Playground For The Kids - Min Drive From Lake Wilcox & Bond Lake + Many Other Trails - Tons of Different Variety Of Restaurants - Grocery Stores - Multiple Gyms Close By - Coffee Shops - Public Transportation and Much More

Superhost

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

4.93 out of 5 average rating, 206 reviews

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.

4.89 out of 5 average rating, 186 reviews

A spacious living area features a large flat-screen television mounted on the wall, accompanied by ambient lighting. The modern gray sofa faces the TV, while decorative shelves with various items and a small coffee table with a floral arrangement complete the space.

Flat in Richmond Hill

Newly Renovated 2 bdr. Basement apartment

Located in a quiet and peaceful neighborhood on a private street, this newly renovated 2 bedroom with 2 queen sized beds, 2 full bathrooms, basement home is a perfect choice for a short or long stay for the family or anyone needing a spacious place to stay. Right next to Yonge Street and close to the highway that will take you directly to downtown Toronto. Up to 2 additional guests a night, for $50/a person, however ZERO TOLERANCE against any parties loud music or loud talking past 11PM

4.96 out of 5 average rating, 426 reviews

A modern living area is depicted, featuring a dark sofa adorned with decorative pillows and a light wooden coffee table. A circular dining table with white chairs is in the foreground, while a wall-mounted TV is positioned opposite. Warm lighting enhances the spacious feel.

Flat in Richmond Hill

Modern Cozy Home near the Mill Pond Park.

Our newly renovated basement apartment will enchant you with its contemporary style, brightness and coziness (large lookout windows, super bright!). It is fully furnished with style and attention to details so you can feel at home away from home. It is just a few steps away from the beautiful Mill Pond Park - a great place to immerse in the beauty of nature. The park has many lovely trails that you can explore. The apartment has everything you need to make your stay perfect.

4.92 out of 5 average rating, 232 reviews

Flat in Richmond Hill

King Bed! 2 Parking! 55"TV! Side Entr! Private!

Enjoy total privacy in Richmond Hill’s Historic Heritage district! This suite features a private side-door entrance and a massive King Bed. A rare highlight is the dedicated massage room for relaxation. This bright lower-level retreat includes a 55” Smart TV (Netflix/YouTube), fast WiFi, a kitchen with a big fridge, and openable windows for fresh air. Steps from restaurants, cafés, and transit, with 2 FREE parking spots. A private sanctuary in a prime spot. Book your stay!

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.

4.96 out of 5 average rating, 107 reviews

Snow-Free Garage Parking / Modern bright 2BR Suite

Drive directly into your private garage and enter this bright, modern 2BR suite. No snow or rain to worry about—plus a Tesla EV charger is available! The Comforts: Cozy electric fireplace & Smart TV Fast Wi-Fi for remote work/streaming Secure indoor parking included Located in Oak Ridges, you're steps from Grovewood Park and minutes from Lake Wilcox & Canada's Wonderland. A private, modern and newly remodeled retreat—perfect for families or business travelers.

Guest house in Richmond Hill

A spacious living area is furnished with a modern gray sofa and a white TV unit, which holds a flat-screen TV. Natural light enters through sliding glass doors leading to a balcony. In the background, a kitchen with white cabinetry and a dining area is visible.

4.94 out of 5 average rating, 156 reviews

Detached Coach House | 1 Bdrm 1 Bath| Private HVAC

Luxury Detached 1-Bedroom Residence in prestigious Observatory Hill. Unlike nearby studios, this is a true 1-bedroom suite with a separate closing door for quiet and privacy. 100% independent building—no shared walls, no shared air (private HVAC), No Footsteps Above You! Features a condo-style layout with full kitchen, living room, and in-suite laundry. Includes 3Gbps Wi-Fi, 50” Smart TV & Nespresso. Perfect for executives/couples needing space. Parking included.

4.85 out of 5 average rating, 115 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

Escape to a luxury geodesic dome on our scenic farm, nestled at the edge of the forest. Fully equipped with heating, cooling, a private washroom, deck, and hot tub, it’s the perfect blend of comfort and nature. Explore the farm, meet our sheep, chickens, and livestock guardian dog, or hike over 100 acres of connected regional forest. Whether you’re relaxing under the stars or adventuring outdoors, this unique glamping retreat promises an unforgettable experience.

Guest house 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, 101 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!

4.92 out of 5 average rating, 171 reviews

A modern kitchen is presented with sleek cabinetry in light and dark tones. Stainless steel appliances, including an oven and refrigerator, are visible. A large island with bar seating for two is positioned near expansive windows, allowing ample natural light to enhance the space.

Home in Richmond Hill

Studio House with Entrance, Kitchen, Free Parking

Newly painted luxury Studio house, Located in the Heart of Richmond Hill, walking distance from David Dunlap Observatory Park, Plazas, Malls, Schools, Restaurants and Supermarkets. Close To Highway And Go Station, Viva, Yrt. Separate entrance and all inclusive with one queen bed, sofa bed, smart TV, Bell 1.5G speed internet, private kitchen - Fridge, Washer, Dryer, Stove, Oven, Range Hood, Micro oven, and full bathroom with free Parking.

4.95 out of 5 average rating, 235 reviews

A neatly arranged bedroom features a decorative, patterned bedspread on a spacious bed. Two bedside tables with lamps are placed on either side. The wall displays a dreamcatcher design and an uplifting message, contributing to a calming atmosphere. Natural light enhances the inviting space.

Home in Richmond Hill

20%OFF| 0 Cleaning Fee| Mins to Lake| Free Parking

❥ Transportation: 🚗 5 mins to Highway 404. 🎢 20 mins to Wonderland; ✈️ 40 mins to airport. ⛳ 7 mins to Golf. ❥ Privacy: 🅿️ Driveway parking. 🌙 No sidewalks for added quiet. ❥ Amenities: 🛒 Close to Food Basics, No Frills, and 🥢 15 mins to T&T. ❥ Recreation: 🛶 Near Lake Wilcox (boating), 🏊 5 mins to Oak Ridges Center, 🌊 10 mins to Lake Wilcox & Bond Lake, 🥾 hiking trails nearby.

Popular amenities for Richmond Hill family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.92 out of 5 average rating, 101 reviews

A spacious backyard is highlighted by a hot tub, surrounded by soft lighting. A colorful children's playset is visible, featuring a slide and swings. A gazebo provides shade over outdoor seating, while a telescope and fire pit are positioned for evening enjoyment.

Home in Toronto

Backyard Oasis | Hot Tub & Playground

4.94 out of 5 average rating, 283 reviews

A timber frame tiny home is set amidst a snowy landscape, featuring large windows and a private deck. A circular fire pit with flames is situated on a stone patio, surrounded by wooden adirondack chairs, while trees frame the serene pond in the background.

Tiny home in Hamilton

Timber Haven

4.96 out of 5 average rating, 185 reviews

An outdoor fire pit surrounded by gravel is present, featuring two wooden chairs. A hot tub is located nearby, positioned in front of a geodesic dome with large windows. String lights are draped overhead, illuminating the outdoor space.

Dome in Utopia

Glamping Dome Riverview Utopia

4.91 out of 5 average rating, 131 reviews

The modern condo building features a multi-story design with balconies and large windows. Soft greenery lines the ground level, enhancing the urban landscape. A clear blue sky provides a bright backdrop, while the street is lined with manicured trees, creating an inviting atmosphere for residents and visitors.

Apartment in Unionville

Downtown Markham Unionville

5 out of 5 average rating, 140 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.

Apartment in Yorkdale

The Penty: Luxurious Penthouse with Pool, Hot Tub

4.99 out of 5 average rating, 181 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

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

4.98 out of 5 average rating, 626 reviews

A vibrant sunset is captured with layers of orange, red, and yellow hues across the sky. Silhouetted trees and foliage frame the image, creating a contrasting foreground against the colorful backdrop.

Guest suite in Hamilton

Country Getaway in Puslinch

4.9 out of 5 average rating, 269 reviews

Cottage in Innisfil

Utopia villa and spa

Family- and pet-friendly home rentals

Superhost

A glamping dome is set amidst a lush green landscape, reflected in a serene pond featuring lily pads and blooming flowers. Towering trees provide a natural backdrop, while a wooden deck extends from the dome, enhancing the outdoor experience.

Dome in East Gwillimbury

4.9 out of 5 average rating, 251 reviews

Deerleap Glamping Dome

4.93 out of 5 average rating, 162 reviews

A winding path is framed by tall trees, leading to a rustic cabin nestled among the forest. Lush greenery flanks the path, creating a serene and secluded ambiance, inviting exploration into the natural surroundings.

Tiny home in MONO

Whispering Pines Cabin in Woodland Acres

A well-lit bedroom features a spacious bed dressed in a striped white duvet. Geometric patterned pillows add visual interest. A mirror and framed artwork are displayed above a wooden dresser, which holds decorative items and a stylish lamp, enhancing the room's modern decor.

4.95 out of 5 average rating, 109 reviews

Tranquil Ambience with a Private Washroom

4.98 out of 5 average rating, 326 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

Superhost

Two brown horses are depicted in a snow-covered outdoor setting, closely positioned with their noses touching. Flakes of snow gently fall around them, creating a serene winter scene, while a house and snow-covered trees are subtly blurred in the background.

Bungalow in Hamilton

4.92 out of 5 average rating, 220 reviews

Horse Ranch with Hot tub

4.97 out of 5 average rating, 559 reviews

A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.

Treehouse in Port Perry

Treehouse on private, isolated forest (300 acres)

4.96 out of 5 average rating, 113 reviews

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.

Flat in Toronto

Toronto Island Wonderland View

4.81 out of 5 average rating, 109 reviews

1 Bdr + 1 Parking BSMT Apt Sep Entr. Hill Crest Ma

Family-friendly home rentals with a pool

5 out of 5 average rating, 200 reviews

The exterior of a modern two-story home is displayed, featuring a brick and stone facade. A well-maintained driveway leads to a double garage with decorative doors. Bright flower pots are positioned near the entrance, while lush green landscaping surrounds the property.

Flat in Newmarket

The Hilton BnB Adult Luxury Suite

4.94 out of 5 average rating, 239 reviews

A private hot tub is positioned on a wooden deck beneath a lattice covering, allowing for relaxed soaking. Lounge chairs are arranged nearby, and vibrant greenery and decorative flowers provide a natural backdrop. A swimming pool can be seen in the distance, enhancing the outdoor ambiance.

Home in Port Perry

Home away from home with a hot tub and pool

4.95 out of 5 average rating, 342 reviews

A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.

Cabin in Mono

The Trails Retreat (Private Cabin)

Dome in Bradford West Gwillimbury

Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.

4.96 out of 5 average rating, 479 reviews

Four season glamping dome under the stars

4.91 out of 5 average rating, 114 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!

5 out of 5 average rating, 105 reviews

A backyard seating area is viewed, featuring a dark outdoor sectional couch with a black coffee table placed on a striped rug. Surrounding the heated saltwater pool are lounge chairs and lush greenery, creating a serene outdoor space.

Guest house in Brampton

Bright and Airy Guest Suite with Pool

4.96 out of 5 average rating, 150 reviews

A cozy sitting area is presented with a blue checkered sofa and a striped armchair, adorned with nautical-themed cushions. Light is provided by two lamps on either side, illuminating the artwork and rustic wooden beams above.

Guest house in Erin

The Captain's Cottage at Willow Pond