Holiday 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.

Cozy small newly built Toronto Islands getaway

Escape to a modern cottage on Toronto Island Looking onto Lake Ontario is our newly constructed modern home. Enjoy our cozy private guest suite in our family home with a kitchenette, ensuite bathroom, and private entrance Just a quick ferry ride from the bustling downtown core come explore the Toronto Islands which is the biggest car-free community in North America; with beaches, trails & skyline views as well as an amusement park in the summer. We also have 2 bikes you can use to explore.

Charming Liberty Village condo! - Casa di Leo

Enjoy a memorable stay at this unique condo located in the heart of Liberty Village. Just steps from downtown, Toronto’s World Cup Stadium, & Budweiser Stage, you’re never far from the action. 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 choosing Casa di Leo!

King West Loft w/ CN Tower Views • 2BR + Parking

Stay in the heart of King West with unobstructed CN Tower & skyline views from your private balcony. Bright, stylish 2-bedroom, 2-bathroom loft. Perfect for couples, small families, friends, or work trips. Steps to top restaurants, bars, Trinity Bellwoods, and transit. • 2 bedrooms / 2 bathrooms • 1 Queen bed + 1 Double bed • 9 ft ceilings + hardwood floors • Fully equipped kitchen + espresso machine • Private balcony (~100 sq ft) • Dedicated workstation • 1GB high-speed internet + TV

Unique Studio with Sauna

Perfect sanctuary for two with 11' high cedar-ceilinged right in the heart of Toronto. ♡ Architectural designed space with Private Sauna ♡ Outdoor Patio with Firepit ♡ Hotel Inspired Space with Super Fast WIFI ♡ Automated Check in & Check Out ♡ Street Parking ♡ 100/100 Walk Score ♡ 100/100 Transit Score ♡ Walking distance to Queen West ♡ Flexible Check in Check out - Message for Details 4K Netflix ♡ A/C ♡ Coffee Bar ♡ Record Player ❤ Book today! Please note: NO KITCHEN OR LAUNDRY

Stylish 1870s Home near Distillery District & Old Toronto

Visiting for fifa? Stop here...Steps from the Distillery District downtown, this Top rated listing is a beautifully restored 1870s row-house (townhouse) that blends historic charm with modern refinement. Thoughtfully designed throughout, it’s located downtown also close to St. Lawrence Market, and some of the city’s best cafés and restaurants. In the evening, unwind in the serene, charcoal-toned bedroom beneath the warm glow of a statement chandelier—your refined Toronto retreat awaits

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.

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.

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.

Charming Apt w/ Private Deck in a 1890s Victorian

Live like a local in this Toronto Victorian with newly updated kitchen, private patio and plenty of natural light. It even boasts an original stained glass window circa 1890 serving legit heritage vibes. Located just off bustling Queen Street on a quiet one-way; this lovingly maintained second floor apartment has got it all, including free laundry, black out blinds, a TV and super reliable internet access. The sofa can be made into a queen size bed; sleeps 4 comfortably.

Central condo in heart of Liberty Village +parking

Right on the park! Stay in one of Toronto’s most vibrant neighborhoods. This modern space includes high-speed Wi-Fi, dedicated workspace, large HDTV, in-unit laundry, and access to a private gym. ALL amenities withing walking distance Steps to cafés, nightlife, transit, parks, and more. Walk to the Waterfront, BMO Field, RBC Amphitheatre, Enercare center, CNE, Fort York, and top attractions—perfect for work or play.

Backyard Oasis | Hot Tub & Playground

Spacious and family-friendly 4-bedroom home with a private fenced backyard featuring a hot tub, playground, fire pit, and BBQ. Close to downtown Toronto, yet perfect for a relaxing getaway. - Sleeps up to 9 guests - 4 bedrooms, 3 full bathrooms - Free parking and EV charger - Pet-friendly - Crib, high chair, and baby essentials included Need more space? Add our basement suite to accommodate up to 15 guests total.