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Holiday houses in Oakwood Village

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Oakwood Village

  • Total holiday rentals

    Explore 310 holiday rentals in Oakwood Village

  • Nightly prices starting at

    Oakwood Village holiday rentals start at $17 NZD per night before taxes and fees

  • Verified guest reviews

    Over 9,720 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wi-Fi availability

    310 of Oakwood Village holiday rentals include Wi-Fi 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!

Top-rated holiday rentals in Oakwood Village

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Home in York
4.92 out of 5 average rating, 25 reviews

Renovated 2 Bed lower level apt- free parking

Welcome to this modern 2-bedroom basement apartment located in the vibrant Oakwood Village neighborhood. ideal for couples or small families. Located in one of Toronto’s most accessible pockets, steps from St. Clair Avenue West, featuring streetcar, local cafes, shops, parks, and grocery stores. Nearby amenities include Cedarvale Park, Oakwood Collegiate Institute, and the trendy Eglinton West dining strip, proximity to TTC bus routes, Yorkdale Mall, and easy access to Highway 401 via Allen Road

Top Guest favourite
A compact bedroom is furnished with a spacious bed dressed in striped linens. Artwork is displayed on the walls, and a mirrored closet adds depth to the space. Natural light enters through partially covered windows, while soft bedside lamps provide illumination.
Apartment in York
4.96 out of 5 average rating, 157 reviews

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.

Superhost
Home in Toronto
5.0 out of 5 average rating, 4 reviews

House w/ Free Parking | Backyard | BBQ | Piano

Stylish 2-level, 1,500 sq ft (139 m²) house with FREE parking, fast Wi-Fi, central AC, and a private patio with gazebo & BBQ. Enjoy a king bed, fully equipped kitchen, and 75” & 85” TVs with Netflix & Prime. Located in a lively, walkable area with groceries, cafés, restaurants, shops, parks, gym, library, FREE public pool, and 24-hour transit at your doorstep. Easy access to 3 subway stations; downtown/Bloor-Yonge is about 23 minutes by car. Close to Casa Loma, bike share & paid EV charging.

Top Guest favourite
A modern kitchen features sleek white cabinetry and a countertop with a subtle texture. Essential appliances include a stove with four burners, a coffee maker, and a small kitchen rug adds warmth. Light is provided by recessed lighting throughout the space.
Guest suite in Junction Triangle
4.94 out of 5 average rating, 149 reviews

Bright west end 1-bedroom basement suite

A beautiful newly renovated basement suite, with 8ft ceilings, large windows, a glass rainfall shower & 2 comfy Queen sized beds (one is a fold-out sofa bed in the main living space). It's conveniently located close to the UP Express & TTC stations for traveling around the city. The house upstairs has a small child & there will be a certain amount of noise :) Please message me with any questions & I would be happy to answer you. Thanks for stopping by! registration # STR-2207-GGZRVF

Top Guest favourite
Home in Midtown
4.96 out of 5 average rating, 46 reviews

Artful-Elegant-Light-Filled & Fabulous

Stunning first floor of large property. Bungalow style designer suite for upscale comfort and privacy. High ceilings, X-large rooms, new kitchen, 2 full baths, lots of light, private parking, huge front porch, hardwood floors, fireplace, A/C, laundry (shared). Gorgeous tree lined family st w/ 24 hr public transit. Steps to supermarket, parks, ravine area for walking/biking. Fabulous location adjacent to Forest Hill. Steps to restaurants, cafes, shop, subway, Wychwood Barns farmer’s market.

Guest favourite
A modern living area features a sleek brown leather couch with decorative pillows, positioned across from a dark wooden coffee table. Bright natural light enters through large bay windows, complemented by light-filtering curtains. A decorative wall map and a large green plant add character to the space.
Home in York
4.99 out of 5 average rating, 213 reviews

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

Guest favourite
Home in York
4.94 out of 5 average rating, 16 reviews

Free Parking | Transit | Quartz Kitchen | Laundry

Beautifully renovated Toronto home in Corso Italia. Close to downtown and BMO field where FIFA world cup games will be, cafes, and restaurants. This bright, modern space features an open living area, quartz counters and stainless steel appliances, fast Wi-Fi, Smart TV, and in-suite laundry. Located on a quiet residential street with easy access to parks and transit. Perfect for couples, business travelers, or small groups seeking comfort, style, and convenience during their Toronto stay.

Superhost
Guest suite in York
5.0 out of 5 average rating, 4 reviews

Fully Private Suite in Midtown Toronto + Netflix

Enjoy in your private basement: ✅ TV + Netflix in living room ✅ Desk and chair ✅ Complimentary coffee and tea ✅ High-speed WiFi ✅ Laundry facilities ✅ Shampoo, conditioner, body wash & towels This is a private one bedroom basement, with private washroom, private kitchen, and private living room. During your stay, you’ll have access to my beautiful backyard, where you can enjoy the fireplace and BBQ. Please note that this outdoor space is shared with other Airbnb guests and with me.

Guest favourite
Apartment in York
4.85 out of 5 average rating, 26 reviews

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!

Guest favourite
Guesthouse in York
4.95 out of 5 average rating, 21 reviews

Handy Studio in Oakwood Village

Cosy midtown laneway studio is 440 square feet of private, quiet space, 75 ft from street parking. Easy access from Pearson. Large windows on north and south ends ensure great natural light. There are solar shades to keep out the summer heat while allowing the occupant to see out, and privacy curtains for times when they are needed. 4 minutes walk to TTC buses, 12 to subways. Full kitchen, fridge, dishwasher and stove. Wifi. Queen sized Murphy bed folds to maximize space.

Guest favourite
Home in York
4.85 out of 5 average rating, 20 reviews

Casa del Jo | Boho 2BR + Parking + Workspace

☀️ Summer Stays in Toronto! Stylish boho 2BR main-floor suite in a quiet, walkable neighbourhood with easy access to downtown, the Entertainment District, and top Toronto attractions. Relax with fast WiFi, Smart TV, a newly renovated spa-like bathroom, dedicated workspace, and free parking. Featuring cozy king + queen beds, in-suite laundry, and thoughtful touches throughout. Perfect for couples, friends, professionals, remote workers, or longer stays.

Top Guest favourite
Guest suite in York
4.96 out of 5 average rating, 159 reviews

Mid Town MidMod | Private 1BR Unit

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 exploring the city, business travelers seeking privacy and a comfortable workspace, or families visiting relatives. Our private 1-bedroom suite features a queen bed, separate futon, full kitchen, and all the amenities you need for a comfortable stay. Walk to great restaurants, cafés, shops, and transit.

Popular amenities for Oakwood Village holiday rentals