
Family-friendly holiday rentals in Oakwood Village
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Oakwood Village
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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.

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.

Cute Private Apartment near University of Toronto
This cozy main floor apartment with private walk out patio, located on a quiet street in the beautiful Annex neighbourhood. Free parking Laundry in building Shared backyard 5 minute walk to subway (Christie Station) 5 minute walk to Bloor Street, the restaurants and bars of Korea Town, and historic Christie Pits Park. Walking distance to University of Toronto and George Brown College Casa Loma campus. There are a lot of great restaurants, bars and local grocery stores within a short walk.

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.

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

Bright & Cheery Full Basement Suite walk to Subway
Our basement with private keypad entry in Toronto's tree-lined West End is ideal for tourists or folks coming to the city to work. It was completely renovated in early 2025 with a 1950s vintage travel vibe you'll love. Brand new bathroom, full separate bedroom with queen size bed (ENDY mattress), TV, desk, plus living area with fireplace & sofa bed. There is also a kitchenette/laundry. 3 min walk to Jane subway. Ceiling 6'5" with 1 lower beam. We live upstairs--the unit is noise insulated.

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.

Midtown Luxury Yonge/Lawrence Close to Downtown
Located in the upscale Yonge & Lawrence Village in Midtown Toronto. Steps to Yonge St. bus, 5 min walk to the Subway. The heart of the city is within minutes. There are several restaurants, coffee shops, pubs & bars within a 1-5 min walk. Public tennis courts, parks. The suite is completely self-contained. We live on the main floor above, we are usually available help. There is a 75"Samsung TV, 2 Extra large washers and 2 Extra large Gas dryers for all of your laundry needs.

Luxury 2BR + 1Bath Guest suite(3 Queen Beds+1 SB)
Elegant and bright low-level guest suite in the Toronto area near promenade shopping centre. Complete with 2 spacious bedrooms, 1 bathroom, Luxurious design walk-in closet, 75” large Smart TV, Medium Pool Table. Walmart, No Frills, Shoppers, Starbucks and much more … ( less than 5 minutes Drive from the house). As most Canadian houses are made by wood, there is a possibility of noise and footsteps from upstairs, Air conditioners thermostat is controlled from upper level unit.

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.

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’.

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.
Popular amenities for Oakwood Village family-friendly rentals
Family-friendly home rentals with a hot tub

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

Ask re: FALL Specials-Heated Pool-tub Open 365 Day

The Fort York Flat

Lux Waterfront Condo Pool Hot Tub Free Parking

Luxury Stay w/phenomenal view!

Stylish Downtown Toronto Condo with Free Parking

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

Large & Bright 2BR+Den in Midtown w/ Free Parking
Family- and pet-friendly home rentals

Private Lower 1 BR + Sofabed Self Checkin with PKG

Lively 1+1 Lakeview Condo near CN Tower + Free Prk

Studio Apartment

Luxurious Annex/Yorkville 1300 Sq Ft & Parking

Stylish Apartment in Toronto - Long term available

Private 1-br Apartment: Your Secluded Getaway!

5 Km to Toronto Pearson Airport , Sleeps 4-6

Large Artsy Loft w 30ft Ceilings and Natural Light
Family-friendly home rentals with a pool

2 Bedroom 2Bath CN-Tower/Parking

Pet Friendly Condo, Private Terrace, Pool & Gym

The Snug Oasis - Burrow (Near Airport)

Seraya Wellness Retreat

1 Bedroom Suite - DT Core (Office/Bidet/Balcony)

Bright, spacious luxury basement apartment

Condo in Heart of Mississauga

Hidden gem in Humber bay shores Toronto w/ parking
When is the best time to visit Oakwood Village?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £79 | £84 | £88 | £94 | £103 | £111 | £116 | £118 | £115 | £106 | £106 | £103 |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
Quick stats about holiday rentals that are family-friendly in Oakwood Village

Total holiday rentals
Explore 90 holiday rentals in Oakwood Village

Nightly prices starting at
Oakwood Village holiday rentals start at £23 per night before taxes and fees

Verified guest reviews
Over 2,550 verified reviews to help you choose

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
90 of Oakwood Village holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Oakwood Village rentals

4.8 Average rating
Oakwood Village stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Pet-friendly rentals Oakwood Village
- Flat rentals Oakwood Village
- Rentals with a patio Oakwood Village
- Rentals with a firepit Oakwood Village
- Private suite rentals Oakwood Village
- Rentals with a washing machine and dryer Oakwood Village
- House rentals Oakwood Village
- Rentals with outdoor seating Oakwood Village
- Rentals with a fireplace Oakwood Village
- Fitness-friendly rentals Oakwood Village
- Family-friendly rentals Toronto
- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- Clifton Hill
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- Toronto Zoo
- CF Toronto Eaton Centre
- Financial District
- Trinity Bellwoods Park
- BMO Field
- Massey Hall
- Niagara Falls State Park
- Casa Loma
- Dufferin Grove Park
- Legends on the Niagara Golf Course
- Rouge National Urban Park
- Casino Niagara
- Royal Ontario Museum




