Pet-friendly vacation rentals in Oakwood Village

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 · Comfort · Quiet

The Gallery

Welcome to The Gallery - a 1750 square foot loft with city views, space to relax and a vibe you will love. Beautifully decorated, featuring an open concept and thoughtfully curated vignettes throughout. Our home is most suitable for young families & small groups looking for warm place to enjoy and steps away from some of Toronto's best restaurants, parks and culture. Stay, work here, relax here and enjoy the best of Toronto. Primary is on the 3rd flr and is entirely open concept loft style.

Outdoor spaces · Pets · Value

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.

Walkability · Pets · Sleep quality

Large Artsy Loft w 30ft Ceilings and Natural Light

Welcome to one of the last surviving historic live/work lofts in the city! Live the Toronto artist's dream in this 1000 sq ft, 30ft ceiling, 3-level, artistic and spacious pad in the Junction Triangle! Enjoy a light-filled space sandwiched between the hippest neighborhoods of Toronto West - with Bloordale, Roncesvailles and Brockton Village as neighbours you’re only steps away from some of the city’s coolest restaurants, coffee shops, vintage and galleries! Right on the UP express line!

Walkability · Pets · Hospitality

Toronto Island Wonderland View

Toronto Islands are a 10 minute ferry ride away from downtown Toronto. Switch from the hustle and bustle of the city to the tranquillity of one of Toronto's most coveted parks. Unique to any other metropolitan city, Toronto Island has limited vehicle access. This car free area boasts 6 kilometres of nature walks, children and pet friendly access to beaches, Centre island amusement park, artist exhibitions, restaurants and even a nude beach. A perfect getway for the hybrid vacationer.

Walkability · Pets · Layout

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!

Walkability · Comfort · Parking

Spacious & Vibrant

Stay comfortably in this spacious 2-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 is available for up to 2 vehicles.

Outdoor spaces · Pets · Access

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!

Outdoor spaces · Walkability · Sleep quality

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.

Outdoor spaces · Pets · Biking

Backyard Oasis | Hot Tub & Playground | Near DT

Summer in Toronto starts here — a private fenced backyard with an all-season 6-person hot tub, fire pit, BBQ, and a playground the kids won't want to leave. Four bedrooms, three full bathrooms, sleeps 9 comfortably — 15–20 minutes from downtown. Need more space? Add the basement unit for up to 15 guests total. ★ "The backyard is AMAZING!!! The house is super close to the parade and it's walking distance to so many restaurants and shops." — Devon, Caribana 2025

Outdoor spaces · Pets · Sleep quality

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 !

Walkability · Pets · Beach

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. Note: Guests must have reviews. We cannot host stays with young children (no stair gate, outlet covers, etc.)

Pets · Walkability · Decor