Vacation rentals in Toronto

Often ranked among the world’s most livable cities, Toronto balances its towering skyscrapers with a sprawling patchwork of human-scale neighborhoods. Ontario’s glossy capital is the frenetic center of the country’s art, film, and culinary scenes. And it has architectural landmarks to boot, most notably Old Town’s historic Flatiron Building and downtown’s iconic CN Tower, one of the world’s largest free-standing towers. But at the tree-lined street level, you get a far more laid-back vibe. This is equally a city of parks, vintage shops, and diverse restaurants owned by families from all over the world. It’s a place where blocks of warehouses — such as the Distillery Historic District — are artfully converted into buzzy galleries and bars.

Even as the upward expansion continues, with construction cranes rising almost everywhere you look, you’ll still find plenty of free-spirited communities such as global Kensington Market, fashion-forward West Queen West, and Victorian-era Cabbagetown — each set on preserving an independent character. Getting to know the city’s distinct neighborhoods one by one is the best way to find out what makes Torontonians tick.

Toronto experiences four distinct seasons, each catering to different activities. Summer brings festivals and the most visitors to the city’s central neighborhoods, when you can expect a packed calendar of music, culinary, and arts events. The hottest months of July and August are also quite humid. Late summer and early fall bring the turning of the leaves, cooler temperatures, and the celebrity-studded Toronto International Film Festival in September, one of Ontario’s leading cultural institutions. Fall and spring are generally perfect for booking one of the area’s vacation rentals and seeing the most popular attractions that might be overcrowded in the peak of summer. Holiday markets make December and January festive months, though the winter conditions in Toronto can get harsh: Expect below-freezing temperatures and frequent snowfall.

Toronto Island Park

On a muggy summer day, there’s no cooler place in Toronto than this archipelago of 15 small islands in Lake Ontario. Pack a picnic and hop aboard a ferry or water taxi to reach the entirely-car-free Toronto Islands, the quickest way to escape into nature without actually leaving the city. While the islands’ beaches are the main warm-weather draw, you can also rent bikes, head out for a scenic stroll, and hit the amusement park. When snow falls, cross-country skiers, ice skaters, and snowshoers come out for icy views of the city skyline.

Kensington Market

Kensington Market isn’t a market in the traditional sense: It’s a compact and multicultural district notable for its Victorian homes, low-rise storefronts, and culinary vendors. Come here to explore the narrow streets lined with specialty coffee shops, vintage boutiques, art spaces, and bars and restaurants serving dishes from around the world.

Graffiti Alley

Toronto is a city famed for its street art scene, and there’s no better introduction than what’s known as Graffiti Alley, a several-block stretch of Rush Lane that runs alongside the fashion-focused shopping street Queen Street West. This splashy concentration of colorful art between Spadina Avenue and Portland Street has become a neighborhood icon and, of course, a popular selfie spot.