Family-friendly holiday rentals in Richmond Hill

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, 119 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

4.91 out of 5 average rating, 153 reviews

25% Winter OFF, Luxury 3 Bdrms, 2 Baths, 2 Prk

Welcome to our spacious and modern walk-out bright basement! Ideal for families and groups comfortably accommodating up to 10 guests. Amenities You'll Love: Fully Equipped Kitchen High-Speed Wi-Fi & Smart TV Two Free Parking Spots Family-Friendly Prime Location: 20 Minutes to Canada's Wonderland 5 Minutes to Highways 404 & 407 Close to Shopping & Dining We take pride in offering a clean, safe, and welcoming environment for our guests. Book now and make unforgettable memories in Richmond Hill!

Guest house in Richmond Hill

A spacious sleeping area features a queen bed with crisp white linens, a sleek dresser, and a work desk with a chair. A decorative vase of roses adds a touch of color. Natural light enters through the glass doors leading to the patio.

4.95 out of 5 average rating, 165 reviews

Balcony House with Separate Entrance，free Parking

Enjoy the glamour of this spacious, stylish, worry free, upscale place. It is brand new and 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 1 queen bed, 1 double Sofabed if more than 2 guests, 65in smart TV, high speed wifi. Micro oven, Fridge, K-cup coffee machine, full bathroom, patio sittings, 1-2 free parking

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.

4.95 out of 5 average rating, 137 reviews

New Entire 1 Bedroom Coach House Apartment

This completely private independent one bedroom coach house apartment is located in the prestigious Observatory Hill neighborhood in south Richmond Hill. Great for couple or small family, sleeps up to 4 people. Close to malls, public transit, restaurants, parks, library and mins to Hwy 404, Hwy 407 and Toronto. This 2nd floor apartment offers 3 Gbps internet, Nespresso coffee machine, 50 Inch Smart TV, independent AC, furnace, laundry, private entrance with lockbox access and 1 parking space.

4.97 out of 5 average rating, 146 reviews

Home in Oak Ridges

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

4.96 out of 5 average rating, 403 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.

An open living area is presented, featuring a comfortable sofa and a glass coffee table. A large television is positioned against the wall, while natural light enters through double doors leading to a staircase. A piece of wall art and a decorative table add visual interest.

4.94 out of 5 average rating, 106 reviews

A cozy 1B1B basement suite with free parking

The whole group will enjoy easy access to everything from this centrally located place. Separate entrance, comfortable King bed, spacious living area, private kitchen, private bathroom, private washer and dryer, 1 free parking spots. 10 mins WALKING distance to HMart, shoppers and T&T market. 3 mins driving distance to Hillcrest Mall. 5 mins driving distance to Mackenzie Hospital and Library. Countless delicious restaurants, fancy playgrounds and joyful water parks nearby!

The exterior view of a two-story brick house is displayed, featuring a spacious driveway paved with stones. Large windows and a prominent entrance add to the curb appeal, while a well-maintained lawn and surrounding trees provide a touch of greenery.

4.85 out of 5 average rating, 152 reviews

Basement Apartment in Richmond Hill

This is a beautiful super clean and cozy basement apartment at the heart of Oakridge in Richmond Hill which is very safe neighborhood with near local plaza including Nofrills, Mcdonald, grocery store and bus stop. The house location is 8 minutes by walk to Yonge Street and quick drive to the highway. The basement comes with free parking space, inside and outside. Everything is convenient for the guests. Perfect place for a peaceful stay that is easily accessible.

Guest suite in Richmond Hill

The spacious living area features comfortable seating with a grey sofa and accent chairs, accompanied by dark coffee tables. A light-filled kitchen with modern appliances is visible in the background, highlighting countertops and cabinetry. Warm, neutral tones enhance the inviting atmosphere.

4.94 out of 5 average rating, 313 reviews

Spacious 2 BR, 3 beds, sleeps 6, kitchen, laundry

Entire basement Separate entrance 8 large windows 9 feet ceiling 2 bedrooms 3 beds (2 queen beds + 1 pullout daybed) 1 free parking spot (additional Parking is available for $10 per night could be paid on airbnb app) Full Bathroom with towels and hairdryer *** Washer and Dryer in-suite ($15 per load)*** Full kitchen with cookwares Dishwasher Stove with Oven Microwave Kettle, Keurig coffeemaker, toaster Laptop-friendly workspace Cleaned professionally

4.85 out of 5 average rating, 255 reviews

A comfortable sleeping area features a king bed with a light blue coverlet and decorative pillows showcasing a subtle animal print. A white dresser and nightstand are positioned nearby, while framed art hangs on the walls. Natural light enters through a window covered with light-colored blinds.

Flat in Richmond Hill

King Bed! 2 Parking! Kitchen! Side Entr! Private!

Bright King-Bed Suite in Richmond Hill’s Historic Heritage District Welcome! Relax in a bright, cozy lower-level apartment featuring a king bed, full kitchen, bathroom, high-speed WiFi, and a Smart TV with Netflix. Two free parking spots make your stay easy and convenient. You’re in the heart of Richmond Hill’s historic heritage district, just steps from cafés, restaurants, shops, and transit—perfect for couples, remote workers, or leisure travelers.

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.

4.92 out of 5 average rating, 199 reviews

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.

4.88 out of 5 average rating, 169 reviews

A spacious living area features a large sectional sofa arranged around a soft area rug. Light wood flooring is complemented by pale walls and columns. A mounted television and shelves are visible. A dining area is to the right, with a table and chairs.

Flat in Oak Ridges

Large Walk-out private apartment w/ parking

A walk-out basement apartment in Richmond Hill. This sunlit apartment has abundance of natural lighting streaming through the many large windows. It has a full kitchen, a full laundry room with a washer and dryer, a designated parking space for one car, and free Wi-Fi access. Perfect for couples or small families, this apartment comfortably accommodates two adults and up to two children.

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

4.96 out of 5 average rating, 151 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, 125 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

4.86 out of 5 average rating, 199 reviews

A vibrant cityscape is illuminated by colorful fireworks, with numerous skyscrapers displaying warm lighting. A large crowd is gathered below, surrounded by modern buildings and open spaces, creating an inviting atmosphere for festivities during the evening.

Apartment in Mississauga

Beautiful Penthouse with Breathtaking View

4.99 out of 5 average rating, 161 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

Year-Round Heated Pool & Hot Tub Family Oasis

4.94 out of 5 average rating, 155 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.

Flat in Mississauga

Luxury Stay w/phenomenal view!

Superhost

A modern living area is shown with a light-colored sectional sofa featuring dark blue accent pillows. A sleek, black coffee table contrasts against the soft, patterned rug. Abstract artwork adorns the wall, complemented by an open layout that invites natural light.

Apartment in Mississauga

4.84 out of 5 average rating, 293 reviews

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍

4.97 out of 5 average rating, 111 reviews

A cabin entrance is framed by tall trees, with wooden steps leading up to a doorway. The cabin combines natural elements with modern design, featuring a blend of wood and metal materials. A person approaches the entrance, creating a welcoming scene in a secluded forest setting.

Cabin in Georgina

Mill Pond Cabin, Nordic Cabin w/ Sauna + Hot-tub

Apartment in Entertainment District

An open-concept kitchen area features a round dining table surrounded by four white chairs. Modern cabinetry and stainless-steel appliances are showcased, with a view of the outdoor balcony visible through large windows. Soft curtains add a touch of warmth to the space.

4.88 out of 5 average rating, 170 reviews

Modern 2 Bd condo near CN tower/MTCC/Rogers Centre

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 463 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

4.87 out of 5 average rating, 472 reviews

A cozy living and dining area features a wooden dining table set with plates and glassware. Two plush sofas surround a glass coffee table in front of a television, while bright yellow flowers add a pop of color to the space. Light-colored walls enhance the inviting atmosphere.

Flat in Berczy

Spacious 2BD 3-6 ppl homestyle BSMT mansion with window basement 130sqm

Superhost

A modern living space showcases a gray sofa adorned with decorative pillows, paired with two white armchairs. A geometric art piece is mounted on the wall, and a small table is set for dining. Natural light enters through the door leading outside.

Flat in Richmond Hill

4.82 out of 5 average rating, 199 reviews

Entire Modern Luxury Apartment + Free Parkings

4.86 out of 5 average rating, 162 reviews

Home in Caledon

Studio Apartment

4.9 out of 5 average rating, 119 reviews

A comfortable seating area is presented with two light-colored armchairs, each adorned with decorative pillows. A low, round coffee table features a small vase of flowers. A floor lamp stands beside the seating area, and natural light streams in through a large window.

Townhouse in Markham

*BRAND NEW*Perfect 4 BR Townhouse Markham *Sleep 8

4.86 out of 5 average rating, 157 reviews

An outdoor patio area is designed with comfortable seating arrangements, including a sectional sofa and ottomans. A pergola provides partial shade over the space, while greenery from nearby trees enhances the natural atmosphere. The wooden deck offers ample room for relaxation.

Home in Oak Ridges

Luxurious Spacious Dream Home with Parking!

4.91 out of 5 average rating, 148 reviews

A modern living space features a cozy sleeping area with a bed adorned in neutral tones and decorative pillows. A dining table with chairs stands nearby, while two comfortable armchairs are positioned around a wooden coffee table. Small plants and wall decor add a touch of style.

Guest suite in Aurora

Fourmi- Cute And Cozy Getaway

4.91 out of 5 average rating, 531 reviews

An open bedroom features a spacious bed with crisp white linens, set against a large window. The window offers a cozy view of a softly illuminated outdoor setting, with string lights glowing in the evening. Warmth is provided by a wall-mounted air conditioner.

Guest suite in Schomberg

Romantic King Suite | Countryside | Pet Friendly

Family-friendly home rentals with a pool

5 out of 5 average rating, 19 reviews

Flat in King City

The King's Rest

4.99 out of 5 average rating, 198 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

4.98 out of 5 average rating, 556 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)

5 out of 5 average rating, 127 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

Apartment in Richmond Hill

A modern kitchen features sleek cabinetry, stainless steel appliances, and a spacious island with seating for four. Natural light floods in through large windows, complementing the contemporary design. Decorative elements add a touch of elegance to the functional cooking space.

4.98 out of 5 average rating, 40 reviews

Chic Richmond hill Condo

4.99 out of 5 average rating, 129 reviews

A modern living room features a gray oversized sectional sofa adorned with various decorative pillows. A circular wooden coffee table and a potted plant enhance the space. The wall is decorated with a large, abstract artwork, and light filters through sheer curtains, creating a serene atmosphere.

Flat in Fort York

The Fort York Flat

Superhost

A spacious bedroom features large windows, allowing natural light to fill the room. A comfortable bed is centered against a dark accent wall, complemented by minimal artwork. A round mirror hangs on the adjacent wall, and warm lighting is provided by a bedside lamp.

Flat in Mississauga

4.88 out of 5 average rating, 109 reviews

Condo in Heart of Mississauga