Family-friendly holiday rentals in York

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.

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

Bright west end 1-bedroom basement suite

A beautiful newly renovated basement suite, with 8ft ceilings, large windows, a glass rainfall shower & 2 comfy Queen sized beds (one is a fold-out sofa bed in the main living space). It's conveniently located close to the UP Express & TTC stations for traveling around the city. The house upstairs has a small child & there will be a certain amount of noise :) Please message me with any questions & I would be happy to answer you. Thanks for stopping by! registration # STR-2207-GGZRVF

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

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

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!

Cozy and Chic Gem in the City

Entire lower level unit. Very clean and cozy unit in a great friendly neighborhood. The unit is bright and airy. The bathroom and kitchen is yours to use. Separate entrance through the side door of the house. Closet space to store your luggage and clothes. Coffee machine with pods and kettle are at your disposable. Extra blankets and pillows are available upon request. While the unit offers a private setup, the main house may also be accessed or shared as per your needs.

Cozy Junction Studio | Walk to Cafés & Transit

Modern newly renovated studio for 2 in Toronto’s vibrant Junction neighborhood. Clean, bright, and comfortable space with fast Wi-Fi and easy self check-in. Located in a walkable area surrounded by great cafés, restaurants, and grocery stores, all just minutes away. Public transportation nearby makes it easy to reach downtown Toronto and High Park. Perfect for couples or travelers looking for a convenient, comfortable stay in one of Toronto’s most lively neighborhoods.

Modern Retreat in Trendy JUNCTION Neighbourhood

A newly renovated, hotel-inspired lower level suite nestled in Toronto’s buzzing Junction neighbourhood. This vibrant, bright basement, brought to life by its charming and colourful accents, is a quick stroll from a variety of restaurants, breweries, parks, and shops. With public transportation steps away, it's the perfect base for exploring the neighbourhood and the city beyond. And, of course, for unwinding afterward.

Private, Spacious,Separate Entrance, Bath, Parking

My Airbnb is located in a green and safe valley between one of the biggest Toronto parks and Bloor West Village/Junction just steps away from trendy cafes and shops. Our Airbnb has a separate entrance. Stunning biking trails are 2 min walk at Etienne Brule gate and lead to Lake Ontario passing Old Mill or north, James' Gardens. You can see salmon traveling upstream of the Humber River in the Fall.

Renovated Modern 2 Bedroom Suite w/ City Views

Experience the city like a local in this newly renovated two-bedroom suite. This ample, bright, airy space has beautiful city line views. We are centrally located (steps away from Casa Loma and downtown) with plenty of options for food, drinks, and local shops. The area has excellent walkability and great transit access. 24km from/to Pearson Airport and 6km from/to Billy Bishop Airport

The Snug Oasis - Woodstock (Near Airport)

Make some memories at this enchanting, family-friendly ranch style estate. Welcomed by old Oak trees and classic stone facades, your suite is on the ground floor. A warm wooden chamber abundant in antique charm, it overlooks the gorgeous garden and resort size pool. Birds chirping, bunnies visiting; nearby restaurants and poolside barbecues make it the perfect retreat!