Family-friendly holiday rentals in North York

The Penty: Luxurious Penthouse with Pool, Hot Tub

Welcome to our modern & luxurious corner penthouse! Stylishly designed with lush greenery and upscale touches, this bright space offers comfort, elegance, and a relaxed tropical vibe. Take in stunning panoramic city views and unwind with premium amenities including an outdoor pool, hot tub, and steam room sauna. Just a 15-min drive to downtown. Public transit at the doorstep. 10-min drive to Rogers Stadium. Perfect for discerning guests seeking an elevated stay in Toronto’s vibrant urban core

Beautiful Modern Home, Heart of Bayview Village

Stay with confidence at a 6-year Airbnb Superhost home known for exceptional cleanliness and care. This bright 3-bedroom, 2-bath unit offers far more space than a typical hotel or condo, plus a private backyard, a rare city retreat to relax, enjoy a morning coffee, or unwind after a day out. Located minutes from Bayview Village, it features up to 2 dedicated parking spots, a comfortable layout, private bedrooms, and inviting living areas, ideal for families, professionals, and longer stays.

Stylish 1870s Home near Distillery District & Old Toronto

Visiting for fifa? 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

Quiet Vaughan Retreat near Wonderland & Hwy 400

Enjoy a stylish and peaceful stay at this centrally located one-bedroom lower-level unit, perfect for both leisure and business travelers. With your private entrance, parking, and all the essentials, it’s your ideal home away from home. Features include a full kitchen, bathroom, internet, smart TV, one Queen and one sofa bed, and a functional workspace. Steps from FreshCo, Walmart, restaurants, and services. Minutes to Vaughan Mills, Canada’s Wonderland, Cortellucci Hospital and transit.

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

Toronto Vacation | ➊ The One Toronto Villa

The One is a unique luxurious private midle-century modern villa escape in the center of north Toronto. Having a stunning and spacious lawn for events and social gathering, this modern house is featured a thermostatic indoor swimming pool. Being inspired from a farmhouse building, the house offering a traditional touch on the vintage furniture and a rustic interior that gives a warm and cozy feelings. It is a great escape from the hustle and bustle of city life without going out of town.

Designer Sunset view unit | sleep 4 | free parking

Enjoy a stylish experience at this centrally located brand new place. ⭐️ Amazing and spacious 1 Bedroom (queen size bed) ⭐️ Queen size sofa bed/pull out couch (can sleep 2) ⭐️ Big 3 piece bathroom with tub. ⭐️ High floor with unobstructed sunset view of Toronto ⭐️ huge balcony with seatings (chairs and tables) ⭐️ In unit laundry ⭐️ 2-4 minutes Walking distance to Metro and public transit (North York station) ⭐️ surrounded by many restaurants and bar ⭐️ 1 indoor parking in garage

Cozy Studio with Private Bathroom and Kitchen

Prime opportunity to rent a bachelor suite in a newly renovated basement in a quiet, highly sought-after area of Thornhill. ​This is a premium rental experience designed for comfort, safety, and modern living. ​✨ Key Suite Features ​Private Bathroom with access from the bedroom. Private Kitchenette with a sink, fridge, microwave and cooktop. The laundry room is shared with other tenant(s). ​Private Entrance: Dedicated entrance from the backyard—no need to go through the main house.

Modern Cozy Home near the Mill Pond Park.

Our newly renovated basement apartment will enchant you with its contemporary style, brightness and coziness (large lookout windows, super bright!). It is fully furnished with style and attention to details so you can feel at home away from home. It is just a few steps away from the beautiful Mill Pond Park - a great place to immerse in the beauty of nature. The park has many lovely trails that you can explore. The apartment has everything you need to make your stay perfect.

The Bubble Glamping Dome

Escape to a luxury geodesic dome on our scenic farm, nestled at the edge of the forest. Fully equipped with heating, cooling, a private washroom, deck, and hot tub, it’s the perfect blend of comfort and nature. Explore the farm, meet our sheep, chickens, and livestock guardian dog, or hike over 100 acres of connected regional forest. Whether you’re relaxing under the stars or adventuring outdoors, this unique glamping retreat promises an unforgettable experience.

Fun Group Getaway | Great Location | Yonge+Steeles

Welcome to the Madawaska Retreat -- a professionally designed vacation rental home in the heart of North York, steps away from Yonge & Steeles! This vibrant retreat is a perfect spot for families or groups of travelling friends. Inside, you'll find three bedrooms that pop with fun wallpaper and cozy vibes, two full bathrooms, entertainment for the whole family and a fully stocked large kitchen, perfect for cooking meals! Two parking spaces included.

Bright Mid-Mod Stay

Stylish 2BR walk-up basement suite in uptown Willowdale! Mid-century modern charm with vibrant decor, natural light, and cozy comfort. Features 2 baths, a kitchenette, laundry, a fireplace, WiFi, TV, and free parking. Pet-friendly with backyard access. Just a 15-min walk to the subway, 2 mins to the bus, restaurants & groceries. Quiet, safe neighbourhood—perfect for solo travellers & professionals. Just peace, style, & sweet city access.