
Holiday houses 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.

Chic Midtown Toronto Suite / Newly Renovated
Welcome to our stylish and newly renovated suite located in the trendy St. Clair Avenue West area of Midtown Toronto! The suite features a spacious bedroom with a plush queen-sized bed, a fully equipped kitchen with brand-new appliances, and a sleek bathroom with a luxurious rain shower. Enjoy the convenience of being just steps away from top restaurants, cafes, and shopping in one of Toronto’s most vibrant neighbourhoods. 20 minutes walk to St. Clair West station, 5 minutes to the streetcar.

Spacious 1 BD basement apartment
Forget your worries in this spacious and serene space. Peaceful neighborhood in central Toronto. This unit is everything you need. Perfect for couples. 700 sq ft, brand new furniture, transit-friendly and a 10 minute walk to a variety of restaurants and coffee shops. Transit will take you in Downtown in 20 min. Fresh linens, towels, Wi-Fi, coffee maker, toaster are provided. Guests have a private seperate entrance. I want people to feel comfortable in the space 6ft max height is recomended.

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.

Cozy and Modern Lower-Level Suite in Corso Italia
Welcome to your home away from home! This newly updated, bright and cozy suite is nestled in Toronto’s buzzing Corso Italia neighbourhood. This apartment offers the perfect blend of comfort, privacy, and convenience. Whether you're here for a short stay or a longer getaway, you'll enjoy a comfortable retreat in this recently renovated and thoughtfully designed space. You will have access to the entire apartment accessible via a separate entrance located in the backyard.

1 x Bedroom Modern Apartment (2xBeds)
Enjoy the bright 1 x bedroom and business friendly basement apartment with complete separate entrance. Newly renovated space. 8ft Ceilings throughout. Centrally located for easy access to downtown and uptown. In suite laundry & wifi and Netflix as well. It is a basement apartment so people live in the unit above. The apartment has been built to code with acoustic insulation. No parking available. Street parking permits available. No parties, smoking or loud groups.

Luxe Edition Private Room#2 Koreatown DT Toronto
Kick back & relax in this calm, stylish space ✨ Enjoy a cozy private bedroom 🛌 in a detached home 🏡 with your own washroom 🚿, workspace 💼 & shared living area 🛋️. Perfect for solo travelers, students 🎓 or professionals 👩💻. Located in a peaceful neighborhood 🌳 with easy access to transit 🚆, shops 🛍️ & food (close to Korean town) 🍽️. Clean, quiet & comfy — your home away from home 💖 Feel free to reach out with any questions! 😊

FREE parking- cozy, inexpensive room in bsmt
Enjoy your place in our cozy place at very convenient location. This apartment is prepared especially for you, . We have free Wifi with fiber optic cable and more than 4 parking space so that you can enjoy your stay. We provide breakfast with cereal, breads, milk, tea, coffee with many flavors to choose. If you need iron, shampoo, or any travel essentials, we got them all for free. Note: *PLEASE REMOVE SHOES AT THE ENTRANCE

Toronto-seperate apartment, free parking &laundry
**Free Parking* ***seperate entrance, keypad*** Explore Midtown Toronto on foot, by bus or streetcar; 2 minute walk to the Dufferin bus, 8 minute walk to the Oakwood bus or take a stroll, and walk 20 minutes south to St. Clair. On St. Clair, ride the streetcar or walk east and west. St. Clair offers a variety of shops, restaurants, bars and pubs. Then return home to relax and wind down in this cozy space.

Cozy private suite on Corso
Private basement suite in Corso Italia! A cozy, relaxed and quiet space to wind down with your own entrance, bathroom, and kitchenette. Perfect for a solo traveller or couple. Access to downtown west end Toronto by public transit: 4 bus routes 2min, 8min, 9min and 10min walk away. Food and drink nearby on St Clair, cool bars on Geary, Dupont, and Bloor. Beautiful walks nearby in Prospect Cemetery.

Casa del Jo | Boho 2BR Retreat + Free Parking
Stylish boho 2BR main-floor suite tucked in a quiet, walkable neighbourhood — just 1 bus to downtown Toronto, Entertainment District, and Financial District! Enjoy a luxury renovated bathroom, cozy king + queen beds, fast WiFi, and free parking. Ideal for professionals, mature students, or digital nomads on longer stays. Close to transit, St. Clair, Casa Loma, George Brown, Yorkdale & more.

Mid town Toronto LGBTQ Friendly Chic & Comfortable
This urban chic place is perfect for solo, or couples/friends on vacation or business. Centrally located in mid-town Toronto between two subway stops (St Clair and Davisville on Line 1) plus 24 hour bus service, you are only 15 minutes from downtown or a 8 minute drive. On street parking is free! I look forward to hosting you in Toronto, the world’s most multicultural city !

Private Studio Downtown Private, Entrance
Hotel Experience, Private exit/entrance with lockbox 24/7. No shared spaces. Downtown core. Other Rentals in this building. The space is 28 square meters. Location across from famous, upscale Summerhill Market in the vibrant Annex hood. Bustling, busy street. Excellent WIFI, Netflix, Prime ready to go. We cater to travelers.
Popular amenities for Oakwood Village holiday rentals
Other great holiday rentals in Oakwood Village

Room#4 in West-Toronto

First floor 1 bedroom in A Beautiful Toronto house

Beautiful Oasis: Private Bedroom/Bathroom

Comfy Home Downtown Toronto

Cozy and Bright Retro Retreat in Upper Junction

Private Oakwood Gem Cozy Urban Retreat

Private Room in Toronto

Private room & washroom
When is the best time to visit Oakwood Village?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $114 NZD | $110 NZD | $112 NZD | $118 NZD | $128 NZD | $137 NZD | $150 NZD | $157 NZD | $153 NZD | $139 NZD | $148 NZD | $123 NZD |
| 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 300 holiday rentals in Oakwood Village

Nightly prices starting at
Oakwood Village holiday rentals start at $18 NZD per night before taxes and fees

Verified guest reviews
Over 9,520 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wi-Fi availability
300 of Oakwood Village holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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 fire pit Oakwood Village
- Pet-friendly rentals Oakwood Village
- Private suite rentals Oakwood Village
- Rentals with a washing machine and dryer Oakwood Village
- Rentals with outdoor seating Oakwood Village
- House rentals Oakwood Village
- Fitness-friendly rentals Oakwood Village
- Apartment rentals Oakwood Village
- 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




