
Holiday rentals in Oakwood Village
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Top-rated holiday rentals in Oakwood Village
Guests agree: these stays are highly rated for location, cleanliness and more.

Cozy 1-bdm suite filled with amenities & parking
A whimsically decorated basement apartment with a separate entrance that welcomes all. The exposed brick gives it a unique character and the location means you're not too far from downtown, close to public transportation and away from congestion. Enjoy amenities such as a kitchenette with all the fixings for a continental breakfast, plentiful snacks and refreshments. The kitchen offers an induction cooktop & toaster oven instead of a stove. Guests can enjoy Netflix, Wifi, and free parking.

Cozy small newly built Toronto Islands getaway
Escape to a modern cottage on Toronto Island Looking onto Lake Ontario is our newly constructed modern home. Enjoy our cozy private guest suite in our family home with a kitchenette, ensuite bathroom, and private entrance Just a quick ferry ride from the bustling downtown core come explore the Toronto Islands which is the biggest car-free community in North America; with beaches, trails & skyline views as well as an amusement park in the summer. We also have 2 bikes you can use to explore.

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.

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

Sleeps 4 • World Cup Ready • Quick Ride to Stadium
Stay comfortably in this spacious Toronto 1-bedroom apartment that sleeps up to 4 guests—perfect for couples, friends, or World Cup visitors. Located in vibrant Corso Italia, you’re just steps from transit with easy access to downtown and stadium events. Enjoy a bright, private upstairs unit with plenty of space to relax after a day exploring the city . This unit comfortably sleeps 2–4 guests. A second queen bed is set up for FIFA for larger groups. Parking available for up to 2 vehicles.

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

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

Urban Retreat Steps to Transit, Dining, & Shops
Welcome to your modern urban retreat in Toronto’s vibrant St. Clair West neighborhood! This bright, stylish 1 bedroom apartment sits in a lively area surrounded by cozy cafes, restaurants, local boutiques, and parks. Enjoy being just steps from express transit for quick access downtown or sites across the city. Our space is perfect for business trips, solo travelers, couples, small groups, or families looking for a home base in one of Toronto’s most vibrant neighborhoods!

Toronto House with Free Parking
**NO Cleaning Fees!** Unplug and enjoy all that the area/city has to offer. Your family will be close to everything when you stay at this centrally located newly renovated place. TTC street cars and bus stops just mins away. Lots of public transit options to take you downtown in just 20mins or less. Please ensure that the house rules have been read before booking. For guests staying 5 days or more, will have access to laundry on site.

Stunning 3B+Garden Oasis @ Wychwood. Top location.
Fully renovated 3BR home in vibrant St. Clair West. Bright, open layout with full kitchen, private garden with BBQ, and sunroom with dedicated workspace. Sleeps up to 7 with 3 bedrooms + sofa bed in the lower level. Walk to top restaurants, shops, and transit. Ideal for families & professionals. Quiet, stylish, and entirely yours — the perfect Toronto stay.

Spacious 4BR Home with Backyard and Parking
Welcome to a spacious, design-forward home in the heart of St. Clair West Village, one of Toronto's most walkable and culturally rich neighbourhoods. With four queen bedrooms, two full bathrooms, a backyard patio with BBQ, and free parking, this home is made for groups and families who want real space and a real neighbourhood to come home to.
Popular amenities for Oakwood Village holiday rentals
Other great holiday rentals in Oakwood Village

Classy penthouse with great views

Handy Studio in Oakwood Village

Super Cozy Room in Corso-Italia

Urban Retreat

Classic Toronto 2 bedroom Apartment

The Cozy Bungalow in North York Nest

Cozy suite in Oakwood Village

A cozy suite in transit friendly Corso Italia.
When is the best time to visit Oakwood Village?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £47 | £46 | £47 | £49 | £53 | £57 | £62 | £65 | £64 | £60 | £58 | £59 |
| 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 in Oakwood Village

Total holiday rentals
Explore 290 holiday rentals in Oakwood Village

Nightly prices starting at
Oakwood Village holiday rentals start at £7 per night before taxes and fees

Verified guest reviews
Over 9,510 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wifi availability
290 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
- Private suite rentals Oakwood Village
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- Rentals with a washing machine and dryer Oakwood Village
- Rentals with a patio Oakwood Village
- Rentals with a firepit Oakwood Village
- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Enercare Centre
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Harbourfront Centre
- Distillery District
- Nike Square One Shopping Centre
- Toronto Eaton Centre
- Exhibition Place
- Toronto Zoo
- Trinity Bellwoods Park
- Niagara Falls State Park
- Financial District
- Downsview Park
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Lakeridge Ski Resort
- Casino Niagara




