Vacation rentals with outdoor seating in Parkdale

Ossington Rowhouse + Private Garden

Relax with a glass of wine in your own backyard garden at this romantic urban cottage—a 700 sq ft pied-à-terre on two private floors of a designer's 4-level townhouse just off the Ossington strip. This calm oasis is perfect for couples or business trips, with high-speed internet and flexible work spaces. Cook in the fully equipped kitchen, or discover Toronto's best bars and restaurants a few steps from home. Explore the city easily on foot, plus close transit with a stop right at your doorstep.

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.

Loft-Style Private Studio Little Italy/Ossington

From the exposed brick, to original artwork, to massive private bathroom with double vanity, this basement suite in our home has been renovated and decorated to feel like a loft. The double bed is brand new with a 16" mattress sure to deliver an excellent night's sleep. You will find a brand new, 42" smart TV resting on a unique mantlepiece refashioned from an antique upright piano, as well as a kitchenette with convection oven/air fryer, Keurig coffeemaker, and stainless steel mini fridge.

Lovely 2-bed / 2 bath Loft in King West w/ Parking

Cosy, Clean and well laid out 2 Bedroom / 2 Bathroom apartment in DNA 1 located in Trendy King West! 9 Ft Ceilings, Hardwood Floors, Stainless Steel Appliances, Gas Stove, Gas BBQ with 100 Sqft Balcony. Unobstructed views of CN Tower and Skyline. Steps out to TTC, Restaurants (Ossington / King West), Bars, Shops, Gorgeous Trinity Belwoods & Liberty Village! 1 Queen Bed 1 Double Bed Satelite TV 1 GB Internet Workstation Kitchen is equiped with everything you need Espresso Machine Large Patio

Bright & Cheery Full Basement Suite walk to Subway

Our basement with private keypad entry in Toronto's tree-lined West End is ideal for tourists or folks coming to the city to work. It was completely renovated in early 2025 with a 1950s vintage travel vibe you'll love. Brand new bathroom, full separate bedroom with queen size bed (ENDY mattress), TV, desk, plus living area with fireplace & sofa bed. There is also a kitchenette/laundry. 3 min walk to Jane subway. Ceiling 6'5" with 1 lower beam. We live upstairs--the unit is noise insulated.

Downtown Condo With a View! - Casa di Leo

Enjoy a memorable stay at this unique condo located in the heart of Liberty Village. Just steps from downtown Toronto, BMO Stadium, & Budweiser Stage, you’re never far from where you need to go. With beautiful unobstructed park and city views, you can take it all in while you enjoy your little slice of paradise. The condo is designed with warmth, character, and meaning to feel as welcoming and comfortable as possible. You’ll instantly feel at home here. Thank you for thinking of us!

Luxury modern Victorian - private parking included

This recently renovated gem has all of the comforts of home, with a fully appointed kitchen that has everything you need to cook a great meal. Nespresso coffee and a selection of teas are also included. Two Smart TVs and a Bluetooth speaker for entertainment. Two comfortable beds and a spacious spa bathroom will make your stay feel like home. A work remote work set up is available for those who require it. The private backyard includes a gas BBQ and private parking is included.

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.

Brock Avenue Escape - Entire Apartment

**BMO Field - home of Toronto’s 2026 World Cup matches - is just 7 minutes by car or taxi, 20 minutes by transit, or a 29-minute walk away** Welcome to this chic, modern apartment on Brock Avenue and its vibrant neighbourhood. Perfect for solo travellers or couples, it offers stylish comfort, great natural light, and incredible city views. Everything you need is within a few blocks - top restaurants, cafés, parks, transit, plus access to a fitness room and outdoor lounge area.

Stylish 1870s Home near Distillery District & Old Toronto

“Rated a Top 10 listing by BlogTO and frequently featured as a must-stay in Toronto. Love thoughtful details? You’ll find them here in this stylishly remodeled 1870s rowhouse. Start your day at St. Lawrence Market, wander through the pedestrian-friendly Distillery District, and explore nearby cafés, restaurants, and bars. In the evening, retreat to the plush, charcoal-hued bedroom and drift off under the glow of a tiered Restoration chandelier. The perfect Toronto stay awaits.”

Luxury Haven in Little Tibet

Discover a haven of luxury in the heart of Toronto's vibrant Little Tibet. Our exquisitely designed home offers a blend of timeless elegance and modern comfort. Indulge in breathtaking views of Lake Ontario from the master retreat's private terrace. Immerse yourself in the beauty of the meticulously renovated interior, featuring high-end finishes and meticulous attention to detail. With its prime location, this is the ultimate destination for an unforgettable stay in Toronto.

Gorgeous Park House on Queen West With Parking

Experience Toronto with style at Park House, where classic character meets modern comfort. This spacious home features a sleek kitchen, comfortable living area, and private terrace—perfect for unwinding after a day in the city. Located in Queen West near Trinity Bellwoods, you’re steps from boutiques, dining, and nightlife. Queen & Ossington is 5 min on foot, Kensington Market 7 min by car, and Downtown just 8 min by car. Book your stay for a memorable Toronto escape.