Family-friendly holiday rentals in Old Toronto

Bright Suite in Little Portugal / Queen West

Our guest suite is bright, spacious & cozy - just down the street from The Drake Hotel. We're in the heart of Little Portugal - tons of amazing restaurants, shops, amenities & cafes in all directions. It’s a great launch pad to explore Queen west / Ossington / Parkdale / Trinity Bellwoods / Dundas West. *Check-in using the keypad on. We keep the space simple and very clean, all the linens & towels are cotton and you'll find organic coffee beans ready to grind + brew! *Pack+play bed available

Cozy 5BR | 4 Bath | 10 Min to DT | Free Parking

Luxurious 5BR/4BA home just 10 mins to downtown Toronto-perfect for family reunions, wedding groups, and large gatherings! Sleeps 12 in comfort with open-concept living, a fully equipped kitchen, 4 Smart TV's, fast Wi-Fi, and a cozy bar area. Enjoy a spacious backyard w/large deck, BBQ, books, board and card games for relaxing nights. Includes free driveway parking, 2 in-unit laundries, keyless self check-in, refined finishes, hotel-quality bedding, and plush towels. Luxury. Comfort. Together.

Cute Private Apartment near University of Toronto

This cozy main floor apartment with private walk out patio, located on a quiet street in the beautiful Annex neighbourhood. Free parking Laundry in building Shared backyard 5 minute walk to subway (Christie Station) 5 minute walk to Bloor Street, the restaurants and bars of Korea Town, and historic Christie Pits Park. Walking distance to University of Toronto and George Brown College Casa Loma campus. There are a lot of great restaurants, bars and local grocery stores within a short walk.

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.

Adorable, modern tiny home in Leslieville

Kick back and relax in this calm, stylish space. 10 minute walk to History! 15 minute walk to the beach! Complete with kitchenette, 3 piece bathroom, and an upstairs bedloft (watch your head - 5'3"). There's a queen bed upstairs and a Spaze pullout sofabed downstairs. Rounding out the space is a TV, highspeed internet, and a minisplit ductless AC/heat pump. Linens and towels are provided. Please note steep stairs and low headroom in the loft. Operator Registration STR-2109-FMGHHC.

Garden Gem | Central | Walk to City's Best Places.

Book GardenGem @HighParkHomes risk-free to get our Insider’s Guide to Toronto's most vibrant places & best discounts. Keep it even if you cancel. 🚶🏻‍♀️WALK to BMO Field •RBC Stage •Little Portugal•Dundas •Bellwoods •Roncy •Little Italy 🚊UP EXPRESS Train in 10 mins to CN Tower, Scotia Arena, Rogers Centre •PRIVATE! High ceilings, heated floors, quality furnishings. ☀️Sunlight fills a big glass entry to lower level, renovated to 9' ceilings. 👨🏻‍🍳Full kitchen. 🧺Laundry ensuite.

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.

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.

Modern Victorian

Modern stay in a Cabbagetown Victorian. Welcome to our renovated, self-contained basement apartment in the heart of Cabbagetown, Toronto. This chic space is ideal for solo travelers or couples. Our apartment is nestled in the charming Cabbagetown neighborhood, known for its Victorian houses, tree-lined streets, and vibrant atmosphere. Cafes, restaurants, and boutiques are within walking distance, and nearby parks offer tranquil escapes. Book now to experience the best of Toronto.

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

Unique Loft in Quiet Pocket | Close to U of T/UHN

Relax and unwind in this unique loft apartment in a rustic house in downtown Toronto! My cat Rikki will be with you also. This space is perfect for anyone looking for a comfy place to stay while exploring what Toronto has to offer. Steps to University of Toronto + Kensington Market. Just north of the entertainment district, 15-min walk to Eaton Centre, 5-min walk to major subway line and University Health Network hospitals. Perfect for couples or single travellers alike!

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.