Family-friendly holiday rentals in Parkdale

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

Bright New Laneway House in Roncesvalles

Bright, brand-new upper-level laneway suite (1BR queen) in the heart of charming Roncesvalles. This sun-filled, modern private space offers comfort, style, and excellent natural light. Steps to cafés, shops, bars, and the Roncy streetcar, with easy access to Queen West. Walk or enjoy a short bike ride to High Park and Sunnyside Beach—an ideal urban retreat in a prime Toronto neighborhood. Street parking available with city overnight permit (12–10 am). Optional garage parking available for a fee.

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.

Unique Queen West Laneway Home

Featured in Dwell, this unique and private detached laneway home is located in Toronto's trendiest neighbourhood, West Queen West. The Scandinavian inspired retreat features an open concept main floor with a walkout to a private patio, a spa like bathroom with skylight and heated floors, 2 spacious bedrooms and is packed full of smart technology and entertainment features. Cozy up for a movie with the 100 inch projector or listen to your favourite music on the full home smart speaker system.

Large Artsy Loft w 30ft Ceilings and Natural Light

Welcome to one of the last surviving historic live/work lofts in the city! Live the Toronto artist's dream in this 1000 sq ft, 30ft ceiling, 3-level, artistic and spacious pad in the Junction Triangle! Enjoy a light-filled space sandwiched between the hippest neighborhoods of Toronto West - with Bloordale, Roncesvailles and Brockton Village as neighbours you’re only steps away from some of the city’s coolest restaurants, coffee shops, vintage and galleries! Right on the UP express line!

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.

Cozy Corners one bedroom ground floor

Cool and cozy downtown main floor in Parkdale! Lake Ontario is 5 minutes away, walking trails and bike path along waters edge. Liberty Village, shopping, great Restaraunts, Ontario Place, CNE, Soccer stadium, many music venues,are all within walking distance. Queen street west is the best ! and is also very close by. Huge fully stocked kitchen with tin ceiling ! Backyard patio. With backyard access. King size canopy bed. Apple TV. Fully private space for work or just hanging out.

Cottage in Toronto’s West End • Near Downtown

A hidden cottage retreat in Toronto’s vibrant west end. Tucked away on a quiet, tree-lined laneway, this fully renovated 1800s cottage offers a rare blend of charm, privacy, and location. Explore Queen West, Ossington, Liberty Village, Exhibition Place, the waterfront, and downtown—then return to your own peaceful retreat. Perfect for families, couples, business travellers, and remote workers, it’s an ideal place to experience the city without sacrificing comfort and tranquility.

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.

Expansive Suite & Stunning Lake Views

Enjoy stunning living space in this beautiful home. With three spacious bedrooms and two full bathrooms—including a luxurious en-suite shower —you’ll find comfort and privacy. Cook up culinary delights in the modern kitchen and take in breathtaking lake sunset views from your balcony. The large living & dining areas are perfect for hosting. Amenities include on-site parking with vehicle charging & laundry. Your perfect getaway awaits!

Modern suite in eclectic Roncy - Queen West

A sleek, newly renovated, bright and airy lower level suite in a charming, century-old Edwardian home with high ceilings, a full modern kitchen, and a relaxing soaker tub. Located in family-friendly Roncesvalles village and Queen West, within walking distance of High Park, Lake Ontario, Little Tibet, Little Italy. Multiple transit options 5 to 10 minute walk from our house, which will take you downtown in 30 to 45 minutes.