Family-friendly holiday rentals in Markham

4.86 out of 5 average rating, 141 reviews

A cozy living area features a plush sectional sofa facing a flat-screen TV. Natural light filters through two large windows adorned with sheer curtains. A small armchair and a coffee table sit nearby, enhancing the comfortable space for relaxation or entertainment.

Home in Markham

New 3BR House, Free Parking, Family & Business

Welcome to your cozy home in Markham/Toronto East -bright, fully furnished 3 bedroom house designed for family comfort, and longer stays. Whether you’re visiting for family, work, or a peaceful break, you’ll find everything you need to settle in easily. - 2 comfortable workstations - Toddler-friendly: crib, high chairs, games - 2 parking spots (garage, driveway) - Close to stores, restaurants, parks, HWY 7/407/401, 15 min drive to Unionville and Toronto Zoo, downtown Toronto 30-40 min drive

Guest suite in Unionville

An open kitchen area showcases modern cabinets, a microwave, and a refrigerator, all complemented by a marble-topped circular dining table with four chairs. A sofa bed with a black and white animal print provides additional seating, while a large window allows natural light to enter the space.

4.94 out of 5 average rating, 121 reviews

Markham, Ontario. Top 1% on AirBnB Ranking.

Downtown Markham. Near grocery stores, Malls, Pan Am Centre, Markham's York University, Main St. Unionville, and restaurants. Transit access to Toronto via the GO train station or by car via the DVP. This modern sub basement has a big window, private full kitchen and bathroom, W/D, A/C, heating, one car parking, comfortable Queen size bed, sofa bed, and a 55" TV. We're very proud to be listed as a "Super Host", "Guest Favourite" & ranked in the top 1% of house listings based on reviews.

4.93 out of 5 average rating, 216 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.

A modern living area features a sleek kitchen equipped with stainless steel appliances, including a microwave and oven. A comfortable sofa is positioned beside a large window, offering natural light. A breakfast bar with stools enhances the inviting space, which includes a neutral-toned area rug.

4.9 out of 5 average rating, 48 reviews

Modern Downtown Unionville Stay

Cozy 1+Den Condo in Downtown Unionville Stay in our modern condo with 11-foot ceilings, two beds, a fully equipped kitchen, and a 4K TV. Enjoy access to the building’s pool and gym for your convenience. Located just 5 minutes from Unionville GO, 30 minutes to downtown Toronto or Pearson Airport, and close to the Markham Pan Am Centre. With restaurants, gyms, and VIP theaters nearby, it’s the perfect base for work or leisure. Book your stay today to experience the best of Unionville!

A modern living area features a light-colored sectional sofa and a coordinating accent chair, complemented by a round glass coffee table. Floor-to-ceiling windows provide unobstructed views of the landscape, allowing for ample natural light. Decorative art pieces enhance the stylish ambiance of the space.

4.9 out of 5 average rating, 58 reviews

Luxury Penthouse | Skyline Views | Markham

Experience luxury living in this top-floor penthouse in Downtown Markham. Relax on the large private balcony with breathtaking skyline views and beautiful changing skies. This spacious 2-bedroom + den, 2-bath suite includes dedicated parking and is ideal for families, business travellers, and extended stays. Steps from Cineplex, restaurants, cafés, Whole Foods, shopping, and the Markham Marriott. Enjoy convenient access to GO Transit and Highways 404 & 407. Hosted by a Superhost.

A modern condominium building features a sleek design with an array of large, floor-to-ceiling windows. The structure rises high, showcasing multiple balconies and a clean architectural facade. The surrounding area offers a sense of urban vibrancy.

4.95 out of 5 average rating, 22 reviews

Luxe 2BR Retreat + Free Parking

Welcome to your stylish corner retreat! This modern 2BR/2BA condo boasts expansive windows that flood the space with natural light. Enjoy spacious rooms, sleek finishes, and a layout perfect for relaxing or working remotely. Located in a vibrant neighborhood with easy access to shops, dining, and transit. Ideal for families, couples, or business travelers seeking comfort and convenience. Includes free onsite parking, paid EV charging and various amanitas, e.g. Gym, reading room.

Apartment in Richmond Hill

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.

4.96 out of 5 average rating, 445 reviews

Modern Cozy Home near the Mill Pond Park.

Our bright and cozy basement apartment features large lookout windows and everything you need for a comfortable stay. Just steps from beautiful Mill Pond Park, enjoy scenic trails and a peaceful residential setting. Located in Richmond Hill, about an hour from downtown Toronto. A vehicle is recommended. Free parking included. Perfect for guests seeking a quiet retreat with easy access to the city and ideal for nature lovers. Shops and restaurants are just a short drive away.

4.86 out of 5 average rating, 530 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.

Apartment in Markham

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

Tips : no party ! ^_^ A cozy basement with seperated entrance and beautiful garden. It locates in a safe and quiet neighborhood of Markham and has easy access to everything, the Village Grocer, Walmart, Markville shopping mall, etc. Ten minutes to go-train to downtown and close to highways going into and out of the city. ^_^您好! 房东是来自上海新移民,热情好客, 全新装修半地下室,完全独立空间，楼上系房东自用，沟通方便，房东万锦其他多处房源亦100%好评, 且常年被评选为最佳房源，位置交通便利,步行达西人超市､渔人村风情酒吧街,10分钟内车程可达10余家华人西人超市,商业广场,等数十家国内各菜系风味餐馆｡

4.93 out of 5 average rating, 14 reviews

Apartment in Unionville

Luxury High-Rise Condo in Downtown Markham

Modern high-floor condo in the heart of Markham with bright open views. Just a 3-minute walk to Whole Foods, plus restaurants, cafes, and supermarkets nearby. Minutes to Main Street Unionville for local dining and charming streets. Includes a fully equipped kitchen, comfortable bed, fast Wi-Fi, and a clean, well-maintained space. Enjoy building amenities such as a gym, indoor pool, and sauna. Easy access to Hwy 404 & 407. Perfect for business trips or short stays.

4.86 out of 5 average rating, 145 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.

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, 108 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!

4.9 out of 5 average rating, 117 reviews

Home in Richmond Hill

Luxury & Cozy 3 Bedrooms Entire Basement

Beautiful and spacious 3-bedroom separate entrance basement unit in Bayview Hill (16th and Leslie). Ideal for families or groups, it boasts a stylish living space, laundry area, and well-equipped kitchenette. In a quiet & safe neighborhood, near parks and restaurants. A few steps away from the local park and the walking trails. Just a 10-minute walk to McDonald's/Tim Hortons/Richlane mall. Private parking and flexible, easy self-check-in.

Popular amenities for Markham family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 127 reviews

Large windows offer a panoramic view of the city, filling the bright living space with natural light. The area includes a cozy sofa set, a dining table with chairs, and a glass coffee table, all complemented by indoor plants and modern decor.

Condo in Richmond Hill

Corner of LOVE

4.92 out of 5 average rating, 118 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!

4.9 out of 5 average rating, 344 reviews

Guest suite in Pickering

Hot Tub Oasis | 35 Min to DT | Main Floor Suite

4.86 out of 5 average rating, 108 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

4.88 out of 5 average rating, 818 reviews

A cozy living area features a brick fireplace with a warm flame, complemented by soft lighting from decorative lanterns. A coffee table is adorned with candles and a chilled bottle of champagne, while comfortable seating invites relaxation.

Guest suite in Pickering

* HOT TUB* Guest Suite - Minutes to the Beach!

Cabin in Whitchurch-Stouffville

A charming cabin is nestled among tall evergreen trees, surrounded by well-maintained landscaping. Stone steps lead to the entrance, illuminated softly by exterior lights. The lush green lawn flows gently, creating a serene outdoor setting.

4.99 out of 5 average rating, 141 reviews

Lakefront getaway for two on Musselman's Lake

4.91 out of 5 average rating, 116 reviews

The modern townhome exterior features a clean brick facade and large windows providing ample natural light. A set of steps leads to the main entrance, framed by black railings on either side. A small potted plant sits at the base of the steps.

Townhouse in Pickering

The Cyberspace (No cleaning fees, Private Hot Tub)

5.0 out of 5 average rating, 159 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

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 192 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

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.

4.96 out of 5 average rating, 112 reviews

Snow-Free Garage Parking / Modern bright 2BR Suite

4.98 out of 5 average rating, 355 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

4.87 out of 5 average rating, 202 reviews

A bright living space is showcased, featuring a comfortable grey sofa with decorative cushions. A stylish glass coffee table sits in front of the sofa. Large sliding doors provide natural light and lead to an outdoor area. Two vibrant yellow chairs and a fireplace complement the scene.

Home in Thornhill

Spacious & bright 2bd Thornhill unit steps to park

4.86 out of 5 average rating, 136 reviews

A warm living area features a large leather sofa paired with a circular chair. A rustic wooden coffee table is positioned in front. Natural light filters through sheer curtains, illuminating the space with a cozy ambiance. A wood-burning fireplace is framed by vertical wood paneling.

Home in Pickering

Cosy 3-Bedroom Home in Quiet Cul-de-Sac.

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.

4.84 out of 5 average rating, 202 reviews

BRANDNEW BASEMENT 2BEDROOM 2BATHROOM FULLY LOADED

Guest suite in Richmond Hill

The living area features stylish furnishings, including a sleek coffee table atop a patterned rug. A reflective mirror enhances the space, while a decorative plant adds a touch of greenery. Natural light illuminates the room, creating a warm and inviting ambiance.

4.88 out of 5 average rating, 105 reviews

Beautiful 2BD basement unit in Richmond Hill

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, 143 reviews

Custom Luxury 2BR | Marble Pool | Games | Fire Pit

Family-friendly home rentals with a pool

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.

4.88 out of 5 average rating, 112 reviews

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

5.0 out of 5 average rating, 204 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.

Apartment in Newmarket

The Hilton BnB Adult Luxury Suite

4.95 out of 5 average rating, 107 reviews

A stone fireplace is set into a rustic wall made of various sized natural stones, providing a textured and earthy backdrop. A flat-screen TV is mounted above, and a wooden cabinet is positioned to the left, adding warmth to the living space.

Apartment in Caledon

Separate apartment with pool, on golf course.

4.97 out of 5 average rating, 116 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)

Apartment in Downtown Toronto

4.92 out of 5 average rating, 157 reviews

Stunning Skyline View Condo, Steps to CN Tower

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, 173 reviews

Rooftop Pool Condo with CN Tower View

4.82 out of 5 average rating, 380 reviews

A modern living area is showcased with a deep blue velvet sofa adorned with two decorative pillows. A glass coffee table rests atop a patterned rug, accompanied by two stylish gold side tables. Large abstract artwork is displayed on the wall, complementing the light-filled space.

Condo in Toronto

Spacious Downtown (midtown) 2bed 2 bath free parki

An open living area features a sleek black couch facing a wall-mounted television. Sunlight streams through sheer curtains, illuminating the space. A wooden table, with several chairs, is positioned nearby, creating a cozy dining area. A large wall clock adds a decorative touch.