
Holiday rentals with outdoor seating in Oakwood Village
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Oakwood Village
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Modern Basement Apartment
Stay in style and comfort at our centrally located Toronto Airbnb basement apartment. Just steps from the #90 bus, which takes you on a short 15-minute ride to St. Clair West subway station, or enjoy a pleasant walk to the station. Exploring Toronto has never been easier. This apartment has two bedrooms and three beds, ensuring ample space for you and your guests to relax in comfort. After a day of sightseeing, unwind in the fenced-in backyard, providing a serene oasis in the heart of the city.

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.

Amazing 1BR Suite Near Downtown!
A private one bedroom luxury basement suite in popular Wychwood has it all: amazing kitchen; open living area with oversized sofa - watch Netflix or cable on the wide-screen TV; dine at a reclaimed wood table; sleep great on a queen size Sealy Posturepedic mattress in the bedroom, 8ft ceilings, private entrance; new washer/dryer! Public transit is steps away. Visit famous Wychwood Barns or shop on St. Clair West - less than 10 min walking. High speed unlimited wifi, premium cable TV, and more!

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

Modern Rustic Laneway Entire Home w/Patio
This cozy historic house is an area that many years ago used to be the apple orchard of John Oakwood, of Oakwood Ave. This rustic brick laneway home is where the apple pickers used to live and a perfect getaway. - A Queen & twin size bed, 3 ppl -A/C -Kitchen -Nespresso/ Frother -Bathroom -Backyard /patio -BBQ -2 Smart TV's -Free Wi-Fi -Laundry - 2 min to closest paid street parking Parking Info Download GreenP App Parking Rates: Day Max (7am – 6pm): $4.50 Night Max (6pm – 7am): $2.50

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

Spacious 3BR Home with Backyard • Great Location
Welcome to a spacious 3-bedroom home—perfect for remote work, or family getaways. With a fully equipped kitchen, large dining area, and cozy living room, there's plenty of room to relax. The lower-level features a big-screen TV, loaded bookshelf, games, and an office desk. Each bedroom offers comfortable sleeping arrangements with fresh linens. Enjoy the private backyard, fast Wi-Fi, and in-suite laundry. A well-designed space that feels like home—whether you're staying a week or a month.

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.

5-Star 2BR/2BA with Pool & Gym | Yonge & Eglinton
Welcome to your high-floor stylish 2-bedroom, 2-bathroom condo in the heart of Toronto! Now accepting bookings through December. Enjoy the indoor pool, gym, hot tub, sauna, steam room, and one free parking spot. Loblaws is downstairs, and GoodLife is across the street. Cafes, restaurants, and parks are within a 2-minute walk. The subway is steps away. The unit includes fast Wi-Fi, Netflix, full kitchen, and in-suite laundry — perfect for work trips, weekend getaways, or extended stays.

Boutique Toronto Home near Downtown
Charming Toronto Retreat – Steps to Shops, Dining & Transit Welcome to a cozy and stylish home located in Toronto’s vibrant York neighborhood. Surrounded by beautiful local restaurants, and boutiques, just minutes from downtown and steps from transit. Cozy & Comfortable: – Bright, inviting spaces – Fully equipped kitchen – Peaceful backyard Short walk to St. Clair West, parks and groceries Perfect for a city getaway, work trip, or family stay, enjoy comfort and in a quiet, central spot.

Bright Modern Private Oasis Lower-Level 1BR 1BA
Newly renovated private lower-level apartment with 1 BR, 1 BA, full kitchen with living and dining area located downtown in the charming Annex West neighborhood. Ideal for quarantine/isolation Your space: - WiFi (75Mbps) - Cozy heated floors - Unlimited hot water - 2-3 min walk to subway and buses - Work remotely in comfort - Child friendly - 2 55" TV's This quiet corner of downtown Toronto sports lots of restaurants, shops, parks, and beautiful streets steps away.

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’.
Popular amenities for outdoor seating rentals in Oakwood Village
House rentals with outdoor seating

Luxury Modern House: Hot Tub, Gym & Steam Shower

Toronto Oasis: Home Near Ossington Strip

Cozy One Bedroom Retreat

Prestigious Private Forest Hill Estate

Incredible Modern 2BR Home with Spacious Terrace!

Luxe Forest Hill Retreat

Tranquility in High Park

Daydream Treehouse
Apartment rentals with outdoor seating

Spacious Riverdale One Bedroom Garden Suite

Your home in Toronto

The Fort York Flat

Toronto's Perfect View Apartment

Condo in Heart of Mississauga

One bedroom vacation rental at The Beaches

Comfort, Style and Privacy.

Bright, Spacious, Quiet 2 bedroom - Licensed
Apartment rentals with outdoor seating

Bright & Stylish 1 Bedroom Condo in King West

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

Modern Residence with Parking @ Heart of Downtown

Hidden gem in Humber bay shores Toronto w/ parking

Stylish Apartment in Toronto - Long term available

Trendy King West townhome

Large & Bright 2BR+Den in Midtown w/ Free Parking

#1 on Airbnb | 2 BR | Free Parking | Sleeps 6 | DT
When is the best time to visit Oakwood Village?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $90 SGD | $90 SGD | $108 SGD | $93 SGD | $123 SGD | $140 SGD | $142 SGD | $146 SGD | $123 SGD | $130 SGD | $119 SGD | $98 SGD |
| 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 with outdoor seating in Oakwood Village

Total holiday rentals
Explore 60 holiday rentals in Oakwood Village

Nightly prices starting at
Oakwood Village holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 2,210 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
60 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!
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- 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
- BMO Field
- Trinity Bellwoods Park
- Financial District
- Massey Hall
- Niagara Falls State Park
- Casa Loma
- Dufferin Grove Park
- Legends on the Niagara Golf Course
- Casino Niagara
- Rouge National Urban Park
- Christie Pits Park




