Family-friendly holiday rentals in Old Toronto

Spacious 1BR Loft • High Ceiling • Walk Everywhere

A bright and stylish urban loft in the heart of downtown! This sun-filled suite features soaring 12-ft ceilings, stunning floor-to-ceiling windows, and sleek hardwood floors. Relax on the oversized sofa, dine at the modern table, and cook in the fully stocked kitchen with stainless steel appliances. Sleep soundly on a plush Westin Heavenly queen bed, and refresh in the spa-like marble bathroom. Includes in-suite laundry, high-speed Wi-Fi, and an unbeatable location near vibrant King Street West!

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, 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 choosing Casa di Leo!

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.

Lux Condo w/ Free Parking, King Bed, Clean, Quiet

Free underground parking! (Very hard to find in downtown Toronto) Renovated condo great for business travelers, remote workers, and arguably the best location for tourists in the city. One of Toronto’s top luxury, Airbnb-friendly buildings. 300 Front Street West sits directly across from the CN Tower and Blue Jays Stadium, just a 3-minute walk to the Rogers Centre, and in the heart of the city's best restaurants and nightlife. Despite its central location, it stays wonderfully quiet at night.

Chic High Rise Urban Retreat with CN Tower View

Imagine waking up to the breathtaking sight of the CN Tower piercing the skyline, its reflection dancing on Lake Ontario. After a day exploring Toronto's vibrant streets and visiting landmarks like the Rogers Centre, the Scotiabank Centre & the magical Ripley's Aquarium, unwind in the living area with panoramic views, or stroll to nearby restaurants and nightlife. Equipped with basic cooking and dining utensils, towels, linens, and bath essentials. Catch your favourite show on the smart TV.

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.

Midtown modern 1 bedroom suite

Located in the heart of Midtown, Davisville Village. Very close to public transit, grocery stores and trendy restaurants. New property, modern look, high-end new appliances (incl. washer & dryer), modern comfortable furniture. Highest standards of cleaning, including proper disinfection of all high-touch areas. All kitchen, bathroom and bedroom supplies for comfortable stay provided. On-site parking is available for a separate fee. High-speed Wi-Fi access, Netflix, cable TV.

Bright Private Basement Suite | 1BR Near Subway

A newly renovated, private lower-level (basement) 1-bedroom, 1-bath suite located in Toronto’s Annex West, just a 3 minute walk to the subway and buses. Bright, quiet, and thoughtfully designed, this self-contained space is ideal for solo travelers, couples, or short business stays. Enjoy heated floors, unlimited hot water, fast Wi-Fi, a full kitchen, and comfortable living and dining areas—steps from restaurants, parks, shops, and beautiful residential streets.

Million Dollar City Views w/ Standup desk, monitor

Gaze at a seemingly unending city view through the floor to ceiling windows of this condo that sits high above the downtown hustle. The 46" HDTV has cable and full streaming, the kitchen is fully equipped with a Nespresso and full sized stove, oven and fridge. Easily work from home at the height adjustable standup desk with 19" external monitor, wireless keyboard and mouse. Perfect for a couple on a weekend getaway or an extended stay of up to 3 months.

Stylish 1870s Home near Distillery District & Old Toronto

Named a Top 10 Toronto stay by BlogTO, this beautifully restored 1870s rowhouse blends historic charm with modern refinement. Thoughtfully designed throughout, it’s steps from St. Lawrence Market, the Distillery District, 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

Cozy Leslieville 2-Bedroom Home

Unique urban home located right next to Greenwood Park where the Leslieville Farmer's Market happens May - October. Perfect for families with children and dogs as the dog park is less than 1 minute away. Convenient access to Queen St. restaurants and the streetcar 5 minutes away. Be downtown Toronto in 15 minutes. Free parking behind house. Explore all Leslieville has to offer.