Vacation rentals in The Annex, Old Toronto

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Top-rated vacation rentals in The Annex, Old Toronto

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Top guest favorite

Condo in Entertainment District

4.96 out of 5 average rating, 219 reviews

Condo in the Downtown City Center

Wake up to city views through the expansive floor-to-ceiling windows of this gorgeous home. It features high gloss fixtures, hardwood floors, and natural textures throughout. Lounge in the open living area and enjoy fresh air on the private balcony. One queen sized bed, but another mattress and air mattress can be provided upon request. The unit comes with an ensuite bathroom. The space comes with a Sonos sound system, WiFi, and a smart TV with Netflix for your enjoyment! A hot water boiler for tea, and a Nespresso machine is available for your use! I am an avid work traveler and this is my personal home, so I've taken a lot of care in picking the furniture, TV, sound bar, Nespresso machine with milk frother, hot water boiler, smart lights, etc. for my space and to share with you for your enjoyment! All I ask is that all guests be respectful of my personal belongings! I'll be available via phone, text, and email to answer all your questions. The apartment is located in the Entertainment District—the heart of downtown. This means walking to some of the city's top restaurants, bars and shopping is easy and convenient. There's an assortment of cafes, patios, convenience stores and gift shops sprinkled on every corner. This is a lively area filled with everything for everybody. Check out the Ripley's Aquarium and CN tower, and catch a game at the Rogers Centre or Scotiabank Arena! Close to the St. Andrew or Osgoode subway station, steps away from Queen Street and King Street (streetcars available), and you can grab an Uber in minutes from this location. Note that there is no onsite parking but there is a parking garage nearby and a few lots. There's an assortment of cafes, patios, convenience stores and gift shops sprinkled on every corner. This is a lively area filled with a lot to explore.

Guest favorite

Condo in Yorkville

4.99 out of 5 average rating, 82 reviews

Luxury Stay in Yorkville/ Prime Toronto Location

Indulge in luxury living at this beautifully furnished 1-bedroom apartment, ideally located in the prestigious Yorkville neighborhood of Toronto. Designed for comfort and style, this serene retreat features high-end finishes and a warm, welcoming ambiance. Just steps from Toronto’s main transit line, you’ll be surrounded by designer boutiques, renowned art galleries, chic cafés, stylish bars, and top-rated restaurants. Whether you’re here to shop, explore, or relax, enjoy the this upscale. Tiff

Guest favorite

Apartment in Annex

4.93 out of 5 average rating, 201 reviews

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.

Top guest favorite

Condo in Yorkville

4.95 out of 5 average rating, 73 reviews

Prestigious Yorkville Condo, Free Valet Parking

High-end buildings in the area with Free Valet Parking through out your stay, doesn't matter how many times you have to leave and come back. Enjoy a stylish experience at the heart of Downtown Toronto. Best restaurants, cafe's, Museum and shopping experience you can have. Less than 1 min walk to Bay street subway station. 5 min walk to Royal Ontario Museum, Queens park, University of Toronto. 2 mins walk to Prada, Cartier, Tiffany's, Chanel, LV, Harry Rosen, Holt Renfrew and many more!

Guest favorite

Apartment in Annex

4.88 out of 5 average rating, 90 reviews

Cozy 1 Bedroom Unit in the Annex, Free Parking

Welcome! This cozy unit is a great place to stay if you want to be in the city without feeling like you're in a concrete jungle. Located in the Annex, it's a food haven for those that are interested in exploring different places to eat. It's also a 5 min walk away from the Bloor/Spadina subway station (or Bathurst station in the other direction), so it's great for commuting around to different areas of Toronto. Yorkville, the ROM, and Casa Loma are also under 10 mins drive from here.

Superhost

Home in Annex

4.87 out of 5 average rating, 98 reviews

Annex Haven: 1 Bedroom plus Den

This centrally located private space is newly updated with new flooring, furniture, and bathroom. It includes a separate entrance with its own kitchen and laundry. Very quiet residential neighbourhood with old growth trees. Walking distance to Christie subway station or Dupont subway station. Be downtown within 20 minutes. Close to Koreatown and many great restaurants on Bloor Street. 5 min walk to 4 grocery stores and LCBO. Basement space not suitable for people over 6 feet tall.

Top guest favorite

Apartment in Annex

5 out of 5 average rating, 39 reviews

Grande Victorian Retreat

Enjoy a stylish, luxury experience at this centrally located apartment on the main floor of a Victorian home. Walking distance to CasaLoma, Royal Ontario Museum, University of Toronto, Yorkville Village Shopping! Only a 2 minute walk to the TTC. The space Living Room: Smart TV and High-speed internet. Bedroom: Queen-sized bed, large walk-in closet, Smart TV. Kitchen: Fully-stocked to make your extended stay feel like home. Bathroom: Large walk-in shower, Washer dryer unit.

Top guest favorite

Apartment in Yorkville

5 out of 5 average rating, 63 reviews

The One in Yorkville-Previously Four Seasons Hotel

Our chic apartment in the heart of Yorkville is within a five-minutes-walk to ROM and Gardener museums, University of Toronto, libraries, theatre, bookstore, parks, subway stations, church, Whole Foods, and all retail stores, from Chanel, Dior, Holt Renfrew, to COS, Sephora, and Winners. Nestled among Park Hyatt and Hazelton Hotel, our building was previously the historic Four Seasons Hotel, and the upscale area around it is bustling with cafes, restaurants and art galleries.

Top guest favorite

Loft in Annex

4.98 out of 5 average rating, 43 reviews

SOHO Warehouse Style Loft in Annex/Bloor St

Welcome to The Annex Loft located right off Bloor St. Experience a rare opportunity to stay in this 1,800 sq ft Brooklyn-style loft, nestled within a historic Victorian house in one of Toronto's premier neighborhoods. Conveniently located near Spadina and Bathurst subway stations, as well as streetcar and bus services, city exploration is a breeze. You’ll also be within a short distance of top Toronto landmarks such as the Royal Ontario Museum and Casa Loma.

Superhost

Home in Annex

4.86 out of 5 average rating, 77 reviews

Charming, Bright Victorian Townhouse in the Annex

3 level, 2-bedroom sun-filled unit situated in the Annex. Brick fireplace (decoration piece), central air conditioning and heating, wooden floors and exposed brick. Steps away from Bloor St, coffee shops, restaurants, shops, galleries, parks and much much more. Short walk to Bathurst or Spadina Subway, Casa Loma, Yorkville, University of Toronto, and museums. One outdoor parking spot provided .

Guest favorite

Apartment in Yorkville

5 out of 5 average rating, 6 reviews

Yorkville’s Chicest Address + 1 Free Parking

This stylish Yorkville condo is your private retreat in Toronto's most exclusive neighbourhood. Steps from designer boutiques, Michelin-starred restaurants, and cultural gems, this space offers both luxury and convenience. Professionally decorated and thoroughly cleaned between each stay, it’s the perfect place to relax after a day of exploring or business meetings.

Guest favorite

Apartment in Yorkville

4.92 out of 5 average rating, 117 reviews

Luxurious Condo in Yorkville + 1 Free Parking

Stay in Toronto’s prestigious Yorkville neighborhood, where high-end shopping, gourmet dining, and art galleries await you. This sleek condo offers total privacy and is professionally cleaned between each guest. Enjoy a stylish, comfortable space with all the amenities for a perfect urban getaway. Ideal for both leisure and business travelers.