Pet-friendly holiday rentals in Oakwood Village

Stylish Apartment in Toronto - Long term available

Stay at our modern 1-bdrm in Toronto’s downtown west end. This private apartment in a classic brick home was recently renovated and features a spacious patio for summer evenings. Inside, modern design mixes with eclectic details, plus a full kitchen and laundry. Local transit is just steps away for exploring the city. This is a 2nd floor apartment only accessible by 1 flight of stairs. Note: Guests must have reviews. We cannot host stays with young children (no stair gate, outlet covers, etc.)

Walkability · Outdoor spaces · Bathroom

Handy Studio in Oakwood Village

Midtown laneway studio has 440 square feet of private, quiet space, 75 ft from street parking. As of Summer 2026, this propery has solar panels and is net zero. Windows on north and south ensure natural light. There are solar shades to keep out the summer heat while allowing the occupant to see out, with privacy curtains for times when privacy is 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.

Walkability · Accuracy · Location

Private 2BR Home Sleeps 6 Near Subway

Welcome to The Laneway Suite! A 1000 sq ft, 2 storey, detached laneway house. Private entrances, Smart Lock, full kitchen with island and all amenities, 1.5 bathrooms, washer/dryer, 2 Queen bedrooms with 32” Smart TV, a living room with a comfy Queen size pull-out couch and 65” Smart TV, a dining room, and a private backyard patio. Whether you’re travelling with your family, your friends, by yourself or on a business trip, this is your perfect getaway! Also suitable for long term stays!

Outdoor spaces · Walkability · Air conditioning

Garden Gem | Central | Walk to City's Best Places.

Book GardenGem @HighParkHomes risk-free to get our Insider’s Guide to Toronto's most vibrant places & best discounts. Keep it even if you cancel. 🚶🏻‍♀️WALK to BMO Field •RBC Stage •Little Portugal•Dundas •Bellwoods •Roncy •Little Italy 🚊UP EXPRESS Train in 10 mins to CN Tower, Scotia Arena, Rogers Centre •PRIVATE! High ceilings, heated floors, quality furnishings. ☀️Sunlight fills a big glass entry to lower level, renovated to 9' ceilings. 👨🏻‍🍳Full kitchen. 🧺Laundry ensuite.

Outdoor spaces · Walkability · Indoor spaces

Comfy Oasis In Historic Downtown Neighborhood

According to Airbnb, we are "One of the most beloved homes on Airbnb". Now in the top 5% of all listings on AIRBNB. Superhosts for 10 years! This renovated guest house features an open-plan kitchen, a spiral staircase to a beautiful and open loft suite, with custom furniture and decorating accessories (1 bed + 1 sofabed). Enjoy the beautiful garden in the summer, and sip any of the more than 15 different complimentary teas and coffees we offer. This guest house is FULLY equipped.

Walkability · Outdoor spaces · View

Spacious Mid Century w/Patio

Adorable Historic Home with Private Patio & BBQ. ♡ 3 bedroom & 1.5 bath (1 King & 2 Queens) ♡ Hotel Inspired Home with Super Fast WIFI ♡ Automated Check in & Check Out ♡ Steps from St. Clair transit line / connects to Subway ♡ 90/100 Walk Score ♡ 100/100 Transit Score ♡ Walking distance to Casa Loma | Rated #1 by BlogTO of Places to Visit in Toronto ♡ Flexible Check in Check out - Message for Details ♡ A/C ♡ Laundry ♡ BBQ & Fully Equipped Kitchen ❤ Book today!

Walkability · Pets · Bathroom

Luxury home with 4 king suites near High Park

Designed for families and groups who want space and privacy, this beautifully renovated Toronto home features four king bedrooms, each with its own ensuite. Walk to Roncesvalles cafés and restaurants, High Park and the Sunnyside waterfront, then come home to bright open living spaces and a private top-floor terrace with glimpses of Lake Ontario. Fast Wi-Fi, a dedicated workspace, self check-in and pet-friendly stays make it an ideal west-end base for exploring Toronto.

Pets · Outdoor spaces · Family

Spacious & Vibrant

Stay comfortably in this spacious 2 bedroom apartment in vibrant Corso Italia, perfect for couples, friends or small groups of friends. Enjoy a bright and private second-floor unit with plenty of space to relax after exploring Toronto. Step outside to enjoy your private patio, or take advantage of convenient parking. With transit just steps away, you’ll have easy access to downtown, Toronto’s attractions, restaurants, and entertainment. Parking included.

Pets · Outdoor spaces · View

Luxury 4BR: 365 Days Open- Heated Pool & Hot Tub

A Private Luxury Getaway in Toronto’s Most Coveted Neighbourhood Escape to an extraordinary 4-bedroom luxury home in Toronto’s iconic Beaches, where sophisticated design meets relaxed lakeside living. This top 1% rated Airbnb property offers an unforgettable weekend experience—perfect for families, couples, or a curated group of friends seeking both comfort and wow-factor. A year round private heated pool and hot tub are yours to enjoy !

Pets · Walkability · Beach

The Robert House: Masterpiece in Harbord Village

The Robert House is a beautiful stylish home in the heart of the city. Located just south of the Annex neighbourhood, east of Toronto’s Little Italy and a stone’s throw from Kensington Market and Chinatown. Enjoy this remarkable home - steps to subway, landmarks, parks, markets, cafes, restaurants, bars & shops. You will remember your stay in this bright & spacious 3+1 bed, 2.5 bath with soaring 10 foot ceilings and high-end finishings.

Pets · Walkability · Getting around

Cherry Blossom House - Overlooking Park

The Gardens Of Wendigo Way are truly unlike any other in the High Park/Bloor West Village Area. This property is on a quiet side street and the home almost sits directly inside High Park. We are tucked away in a valley with a short walk to the gardens ponds zoo and grenadier restaurant. An easy bike ride to the lake. Just steps from Bloor Street and minutes from the core by car. Ideally suited for a family visiting Toronto.

Walkability · Outdoor spaces · Air conditioning

Designer 4 bedroom house - Ossington Station

As featured in Canadian House and Home, this centrally located farmhouse has been renovated from top to bottom. Teeming with light, this spacious house is eclectic, comfortable, and three minutes to the Ossington subway. Relax on the deck to barbeque and entertain. Wander to Dufferin Grove park, the Annex, College St. or Parkdale. Amazing cafes, restaurants and shops within a few minutes walk. Parking for two cars in the driveway.

Pets · Walkability · Access