Holiday houses in Old Toronto

Yorkville | Exec Kitchen | Office | Spa bathrooms

Tucked away on a tranquil street in Yorkville , this 19th-century gem places you steps from the city's most exclusive dining, shopping, and art galleries. Meticulously renovated, you'll enjoy high-end finishes --a Wolf range, Miele appliances, deep soaker tub and custom furniture. The spacious layout features 1 bedroom per floor for ultimate privacy. The home office ensures effortless remote work. When it's time to close your laptop, unwind on 1 of 3 patios, savoring serene city skyline views.

Location · Family · Checkout

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.

Location · Value · Outdoor spaces

New! Private 1BR in Toronto by Danforth, Sleeps 4

Welcome to our stunning, newly renovated home in Toronto’s Old East York neighborhood, just a two minute walk from trendy Danforth Avenue and Pape Subway Station. This bright and airy, coastal-inspired retreat blends the comfort of home with the soothing simplicity of Maritime charm. This private oasis spans 750 square feet and is ideal for those seeking a peaceful escape in East York, with easy access to the best of Toronto. We'd put our accommodations up against the hotels of Toronto!!!

Family · Value · Comfort

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.

Location · Value · Breakfast

Cozy Townhome Condo in the heart of Toronto!

This charming condo townhome offers the ideal pied-a-terre vibe right in the heart of the city. This is the perfect blend of lifestyle and location. Easily accessible to public transportation: • 5 minute walk to Strachan Ave & King Street W line • 15 minute walk to Exhibition Go Station Main attractions: • 10 min. walk to Exhibition Place • 10 min. walk to King Street • 15 min. walk to BMO Field (FIFA World Cup Stadium) • 20 min. walk to Budweiser Stage • 25 min. walk to CN Tower

Family · Value · Solo travel

Charming Apartment with Patio in Midtown Toronto

Beautifully renovated 1-bedroom in a quiet, secure building at Oriole Parkway. Features a brand-new kitchen, modern bathroom, fresh paint, and a spacious private patio perfect for relaxing or entertaining. Steps from Yonge & Eglinton, Eglinton Park, cafés, shops, and transit. Enjoy peaceful living with city convenience - ideal for professionals or couples seeking comfort, style, and location in one of Toronto’s best neighbourhoods. 1 parking spot is available at the property.

Location · Family · Outdoor spaces

Stylish 1870s Home near Distillery District & Old Toronto

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

Family · Location · Parking

Debonair Condo Heart of Toronto w/Free Parking

Enjoy a stylish experience at our centrally located home. Take advantage of charming cafes, Michelin-star restaurants, and boutiques at your doorstep. Steps from the following (walking times) - Financial District - 9 min - St. Lawrence Market - 6 min - Eaton Centre - 12 min - Distillery District - 18 min - St. Michael's Hospital - 9 min Note: there is a new condo building under construction which partially obstructs the view. This is not yet captured in the photo.

Value · Location · Checkout

The One in Yorkville-Previously Four Seasons Hotel

Our apartment in the heart of Yorkville is within a five-minutes-walk to ROM and Gardener museums, University of Toronto, libraries, theatre, bookstore, parks, subway stations, church, Whole Foods, and all retail stores, from Chanel, Dior, Holt Renfrew, to COS, Sephora, and Winners. Nestled among Park Hyatt and Hazelton Hotel, our building was previously the historic Four Seasons Hotel, and the upscale area around it is bustling with cafes, restaurants and art galleries.

Value · Family · Condition

The Riverdale Laneway Suite

Welcome to our stylish new laneway suite nestled in the beautiful Neighbourhood of Riverdale. This modern new build offers two bedrooms, 1.5 bathrooms, a fully equipped kitchen and spacious living space. Perfect for solo travelers, couples or small families. Enjoy the vibrant neighbourhood filled with cafes, shops, parks and and attractions just steps away. Whether you are here for business or leisure our laneway provides the perfect home base for your stay in Toronto.

Location · Value · Air conditioning

John's Island House

Experience the serenity of rural life on Toronto Island while exploring the dynamic city center without getting into a car. Our exclusive island home is quaintly tucked into a forest-lined street connected to pathways with easy access to all the activities the island has to offer. The property is within a three (3) minute walk to Ward’s Beach, the most sought-after sandy beach in Toronto and a fifteen (15) minute walk (including a ferry ride) to downtown Toronto.

Location · Family · Parks

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 !

Family · Location · Long stay