House holiday rentals in Old Toronto

Bright & Spacious 3BR Family Home | Walk to Subway

Stay in a bright & spacious 3 BR home just steps from Coxwell Subway, with direct access to downtown Toronto in 10 minutes. Perfect for families, small groups, or business stays, this home combines space, comfort, and unbeatable transit access in one of Toronto’s best walkable neighbourhoods. This family friendly home is full of natural light and features a spacious kitchen, cozy gas fireplace and a sunroom that opens onto a patio. Unwind in the spa bathroom with a soothing soaker tub.

Value · Location · Condition

Welcome to Greenhills, a Charming Home w/ Parking

Clean Open Concept, Sun-Filled 2 Bedroom main floor home with PARKING; Can sleep up to 4 people. Featuring simple modern décor, queen size beds, big beautiful windows with room darkening curtains, closet storage. Dedicated office desks in bedrooms Full kitchen, with oil, seasoning spices, toaster, hot water kettle, Keurig Coffee Machine and complimentary coffee+tea. Clean bathroom with shampoo+conditioner+body wash+lotion SMART TV 60” Fast internet Wifi Check-In: 3PM Check-Out: 11AM

Family · Value · Comfort

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 · Location · Checkout

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 · Family · Cleanliness

Private Guest Suite with Separate Entrance.

Have this entire guest suite to yourself that's just a 4 min. walk from the beach and the boardwalk. This is a lovely, spacious 1 bedroom with its own open concept living and dining areas with a separate, keypad lock entrance for privacy. Quiet residential street close to public transit, grocery stores, lots of great restaurants and the beach. Wifi, radiant heat in the floors, with full bathroom, laundry, 8 foot ceilings, central air conditioning and 800 sq. feet of living space.

Family · Location · Access

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 · Value · TV

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.

Family · Value · Parks

Private 3BR Whole Home for Groups Near Subway

A newly built, private 3-bedroom, 3-bath home on a quiet laneway in Toronto’s Annex West, just a 3-minute walk to the subway. Bright, modern, and thoughtfully laid out, this entire home is ideal for families or groups traveling together who want to stay in one shared space. Enjoy a full kitchen, heated floors, unlimited hot water, and fast Wi-Fi. Steps from restaurants, parks, and shops, yet calm and private inside. Best suited for guests with confirmed travel plans.

Location · Value · Backyard

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

Location · Family · Layout

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 !

Value · Family · Parking

Toronto Pool Retreat

Spacious and private family home with 5 bedrooms, sleeping up to 10 guests. Enjoy a seasonal pool open May to September (not heated), an all-season hot tub, large backyard, and games area with ping pong, air hockey, and foosball. Includes a fully equipped kitchen, multiple living spaces, and 3.5 bathrooms. Conveniently near Hwy 401, DVP/404, shopping, and supermarkets. Respectful family and group stays only — no parties.

Location · Family · Nearby

Bright & Cheerful Laneway Home

The Laneway suite is my home and was built in 2022 as my dream home in behind an investment property. I’ve equipped my laneway home with all the modern amenities and have tried to give it a real homey feel. I am an artist and my own art is displayed on the walls. I love music so I’ve equipped it with a nice surround sound system. I travel often for work but I’m always reachable through the airbnb messaging system.

Location · Family · Long stay