Holiday rentals in Oakwood Village

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.

3BR/2BA by Subway/ TO- Easy Access to FIFA+Parking

Welcome to our newly renovated 3 bedroom home, in the heart of Toronto. With just a 10-min walk to your nearest subway/metro station, commute to the city is a breeze. A quick 15-20 min drive to the vibrant Downtown Toronto or Toronto Pearson airport. Our location offers convenience & accessibility. Restaurants, shops, cafes, groceries & transit are nearby. * 3 bedroom / 2 bath– Sleeps 6 * Free Wifi * Fully equipped kitchen * Washer & dryer * Professionally Cleaned * Private Parking: 3 cars

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.

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.

CHARMING 3 BEDROOM HOME IN THE CITY W FREE PARKING

Welcome to our clean, cozy 3 bedroom country style bungalow situated in the middle of the city. Close to anywhere you wish to go, but just far enough from all the hustle and bustle. Entire property with 3 bedrooms (1 King and 2 Queen size beds). - Free parking on a private lot for multiple vehicles - 2 televisions - Wifi - Netflix - Kitchen - 2 washrooms - Enclosed private patio and a backyard - Steps to TTC bus stop and 10 min walk to Oakwood Subway - High speed internet and working space

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

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.