Family-friendly vacation rentals in Oakwood Village

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Top-rated family-friendly rentals in Oakwood Village

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
A hot tub is illuminated with soft blue lighting, surrounded by wooden decking and adorned with lush greenery. Soft lighting strands are suspended nearby, creating a serene atmosphere during the evening hours. Brick walls add a warm texture to the space.
Home in Oakwood Village
4.97 out of 5 average rating, 109 reviews

Breathtaking Hot Tub Oasis 6 Guest 3BR 2WR Firepl

Relax and unwind in this downtown Toronto oasis. Trendy St. Clair West is a short 7 minute walk from your doorstep, and offers a wide range of excellent restaurants, bars, cafes, bespoke grocery stores, health food stores and shopping to suit every taste. On Saturdays, make your way to the bustling Wychwood Barns farmer's market for fresh goodies. Need a nature fix? A five minute walk brings you to Cedarvale Park, one of the city's best kept nature preserves. Bus stop located right outside.

Guest favorite
The open-concept living area features a gray couch and a small round coffee table, complemented by a patterned area rug. A dining set with yellow chairs is placed near the kitchen, which showcases modern appliances and sleek cabinetry.
Guest suite in Eglinton West
4.85 out of 5 average rating, 148 reviews

Modern Private Suite By Subway w Free Parking

An entire floor is yours to use privately. Newly renovated with modern amenities, includes a 55" Smart OLED TV, Fibre Optic High-Speed WIFI, and backyard full of fun activities for couples and families. Next to public transit, a quick walk away, is TTC Eglinton W station. Centrally located, quick access to downtown or any neighbouring city (Vaughan, Markham, Brampton, Mississauga). Situated on a quiet street and walking distance from grocery stores, pharmacies, coffee shops, and eating places.

Guest favorite
A Mid-Century Modern themed bedroom features a queen bed with crisp white linens and decorative pillows in warm tones. Floral artwork adorns the walls above the bed. A nightstand holds a lamp and a small vase with flowers, adding a touch of color to the space.
Guest suite in Earlscourt
4.95 out of 5 average rating, 144 reviews

Midtown Mid-Mod

Bright, clean and spacious lower-level guest suite located in Mid-Town’s trendy St. Clair West neighbourhood. Our suite is best suited for adults who want to explore the city and take in the sites, business travelers who want privacy and a comfortable workspace or families visiting relatives. We offer the amenities you’d need and some you wouldn’t expect. Mid-mod inspired bedroom with Queen bed makes for a great place to rest your head after a visiting one of our many trendy local restaurants.

Top guest favorite
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
5 out of 5 average rating, 118 reviews

The Penty: Luxurious Penthouse with Pool, Hot Tub

Welcome to our modern & luxurious corner penthouse! Stylishly designed with lush greenery and upscale touches, this bright space offers comfort, elegance, and a relaxed tropical vibe. Take in stunning panoramic city views and unwind with premium amenities including an outdoor pool, hot tub, and steam room sauna. Just a 15-min drive to downtown. Public transit at the doorstep. 10-min drive to Rogers Stadium. Perfect for discerning guests seeking an elevated stay in Toronto’s vibrant urban core

Top guest favorite
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
4.99 out of 5 average rating, 193 reviews

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

Guest favorite
The entrance of the home features a set of steps leading up to a porch flanked by two lamp posts. A well-maintained garden with potted plants is visible along the pathway. The exterior showcases a combination of light-toned siding and dark accents.
Apartment in Earlscourt
4.9 out of 5 average rating, 167 reviews

Spacious & Vibrant upstairs apartment

There are several shops and restaurants on St. Clair Ave W. Plenty of transit options north of you on the St. Clair line or the bus line on Dufferin. A dog within minutes from the home. The actual space is perfect. Opposite of the open concept apartment, this spacious one bedroom had a separate eat-in kitchen, separate living room, and bedroom. The apartment has the fastest wifi speed. The second floor back terrace has a lovely view with gorgeous sunsets. Parking ✅ Not a shared space.

Guest favorite
A bright and modern space features a cozy red sofa, complemented by a round coffee table resting on a textured rug. A spacious bed is seen in the background, with natural light filtering through a window, illuminating the soft bedding.
Apartment in Mississauga
4.87 out of 5 average rating, 256 reviews

One bedroom Apt. ( 2 storeys unit ) in Mississauga

You will love this one bedroom self-contained 2 storeys unit with separated entrance near Square One mall in downtown Mississauga and 15 minutes to Pearson Airport, easy access to highway 401 and highway 403 and close to all amenities. Modern design bright & spacious with beautiful and private view. Enjoy with free high speed Wi-Fi & 43" tv Netflix available, one parking spot side by side , all included. Quiet neighborhood. - Sorry No party, No smoking, Filming nor Event Stay.

Guest favorite
An inviting sleeping area is highlighted by a spacious bed with neatly arranged pillows. A stylish lamp provides warm lighting, while a full-length mirror is positioned beside the wall. A cozy throw blanket is draped over the bed, and a magazine rests on the bedside table.
Home in York
4.82 out of 5 average rating, 199 reviews

Cozy and Chic Gem in the City

Entire lower level unit. Very clean and cozy unit in a great friendly neighborhood. The unit is bright and airy. The bathroom and kitchen is yours to use. Separate entrance through the side door of the house. Closet space to store your luggage and clothes. Coffee machine with pods and kettle are at your disposable. Extra blankets and pillows are available upon request. While the unit offers a private setup, the main house may also be accessed or shared as per your needs.

Guest favorite
An open-concept living area showcases a comfortable sofa and modern furnishings on a patterned area rug. Natural light streams through large windows, illuminating the space. A wooden floating staircase leads to the upper floor, while a stylish dining space and kitchen are visible in the background.
Home in Oakwood Village
4.9 out of 5 average rating, 207 reviews

Family Home Near St Clair W and Public Transport

Steps away from vibrant St Clair West with great dining, access to public transport and shopping. A real family home with space and amenities for everyone. Free parking for 2 cars. Open-concept living & dining, well-equipped kitchen. Sunny back deck. 3 comfortable bedrooms. Spa bathroom with heated floor. Perfect for families who are in town for reunions, weddings, birthday parties and visiting. Quiet hours after 10pm - not suitable for groups in town ‘to party’.

Top guest favorite
The open concept loft features a spacious living area with large windows and sky lights that illuminate the room. A dining table is surrounded by four chairs, a cozy seating area includes a sofa and a coffee table. Exposed wooden beams accentuate the high ceiling.
Loft in Lorne Park
4.96 out of 5 average rating, 1,063 reviews

Waterfront Coach House Loft

This friendly, private open concept loft apartment is located on the top floor of a guest coach house located on a 2 acre waterfront estate. The loft apartment is a separate building from the main house. There is a maximum occupancy for the loft of 2 people, parties, get togethers and events are not permitted. Due to the tall spiral staircase, children are not permitted due to safety. Extra charges will apply if additional guests are present in the loft.

Guest favorite
A modern living area features a comfortable gray couch positioned near a low white coffee table. A decorative shelving unit displays various sculptures and vases, while light streams in through two small windows above. A neat sleeping area is visible in the background, separated by the shelving.
Guest suite in Eglinton West
4.85 out of 5 average rating, 211 reviews

BRIGHT MODERN STUDIO WITH TERRACE

Bright, airy, modern and new unit with private entrance in midtown Toronto. One minute to transportation, supermarket, bakeries, pharmacies, and all other conveniences. Thirty minutes to downtown and 25 minutes to Yonge and Eglinton by public transport. The space is recently renovated with a small terrace for outdoor space. The unit is self contained with a private kitchen, bathroom and laundry. Sorry, there is no smoking on the property.

Guest favorite
A bright entryway showcases a spacious seating area with a light-colored couch. Decorative plants are placed strategically, beside a standing mirror and a flat-screen TV mounted on the wall. Soft lighting illuminates the modern design, leading to a glimpse of the bedroom area in the background.
Apartment in Stockyards District
4.98 out of 5 average rating, 347 reviews

Modern Retreat in Trendy JUNCTION Neighbourhood

A newly renovated, hotel-inspired lower level suite nestled in Toronto’s buzzing Junction neighbourhood. This vibrant, bright basement, brought to life by its charming and colourful accents, is a quick stroll from a variety of restaurants, breweries, parks, and shops. With public transportation steps away, it's the perfect base for exploring the neighbourhood and the city beyond. And, of course, for unwinding afterward.

Popular amenities for Oakwood Village family-friendly rentals

Quick stats about vacation rentals that are family-friendly in Oakwood Village

  • Total rentals

    90 properties

  • Nightly prices starting at

    ﺩ.ﺇ110 before taxes and fees

  • Total number of reviews

    2.6K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    90 properties include access to wifi

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