
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.

Luxe Forest Hill Retreat
Experience luxury in this Forest Hill home by renowned architect Richard Wengle. Featuring 4 spacious bedrooms (1 king, 3 queens) and 3.5 modern bathrooms, including a spa-like tub, it's perfect for families or groups. Enjoy a home gym, PS 5, Disney+, and Prime Video. Free driveway parking 2 SUVs, Tesla charger, towels, and toiletries included. Just a 10-minute walk to public transit & 15 minutes to downtown. Steps from top dining and shopping, this elegant retreat blends style and convenience.

Live like a local in Dovercourt Village
This renovated, self contained, private basement apartment is part of our historic home located in Toronto's Dovercourt village. There are bars, restaurants, cafes within walking distance. Close to the subway, you can be downtown in 30 minutes. Enjoy being a local, while crashing here at night away from the hustle and bustle of the city. We're bustling family of four that live above you with two dogs and a cat. Sometimes the dogs bark and the cat meows, but if you let us know we'll keep it down.

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.

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.

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

Luxurious Getaway in the City of Toronto
Net Zero Ready home in Toronto designed for professionals, families, and large groups. This architectural gem blends luxury with creative design features. The homes abundant natural lighting gives a warm feel. You can savour a morning coffee on the balcony and relax in the spa like ensuite bathroom. The open concept main room has 12 ft ceilings and creates an inviting space to gather and spend moments with your family and friends. Located close to Toronto's downtown, highways and the airport.

Home Away from Home on St. Clair W./Corso Italia
This charming and beautiful 3-bedroom Century home, full of unique character and warmth, has been lovingly maintained to preserve its original charm with a modern touch. Nestled in a quiet neighbourhood just steps from Corso Italia and St. Clair Avenue West, it comfortably sleeps 6 guests. More than just a place to stay, it’s a true getaway where the vibrant city is at your doorstep, yet the peaceful front and back gardens offers a serene oasis that feels like an Italian villa for relaxation

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.

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

2 level spacious apartment by the lake

Luxury 4BR w/rooftop + parking

Designer 6 Bedroom Sanctuary in Davisville

Modern and Cozy Space in Toronto

Cozy One Bedroom Retreat

Prestigious Private Forest Hill Estate

Charming Cosy Nestled Retreat

Free parking | Modern 3B 1850 sqft Detached House
Apartment rentals with outdoor seating

St Lawrence Market | DT Toronto | Free Parking|Gym

Spacious Riverdale One Bedroom Garden Suite

Your home in Toronto

Sundrenched 1BR Downtwn Apt-Views & Free O/N Prkng

The Fort York Flat

Toronto's Perfect View Apartment

Condo in Heart of Mississauga

One bedroom vacation rental at The Beaches
Apartment rentals with outdoor seating

Bright & Stylish 1 Bedroom Condo in King West

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

Lux Waterfront Condo Pool Hot Tub Free Parking

Modern Residence with Parking @ Heart of Downtown

Hidden gem in Humber bay shores Toronto w/ parking

Luxury Entire Condo At Downtown+parking

Stylish Apartment in Toronto - Long term available

#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 | $131 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!
Destinations to explore
- Family-friendly rentals Oakwood Village
- Rentals with a fireplace Oakwood Village
- Rentals with a patio Oakwood Village
- Rentals with a firepit Oakwood Village
- Pet-friendly rentals Oakwood Village
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- House rentals Oakwood Village
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- Rentals with outdoor seating Toronto
- Rentals with outdoor seating Ontario
- Rentals with outdoor seating 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
- Trinity Bellwoods Park
- BMO Field
- Financial District
- 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




