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Holiday rentals in The Annex, Old Toronto

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in The Annex, Old Toronto

  • Total holiday rentals

    Explore 270 holiday rentals in The Annex, Old Toronto

  • Nightly prices starting at

    The Annex, Old Toronto holiday rentals start at €18 per night before taxes and fees

  • Verified guest reviews

    Over 10,440 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wifi availability

    270 of The Annex, Old Toronto holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across The Annex, Old Toronto rentals

  • 4.8 Average rating

    The Annex, Old Toronto stays are highly rated by guests – averaging 4.8 out of 5!

  • Nearby attractions

    The Annex, Old Toronto’s top spots include Royal Ontario Museum, Bata Shoe Museum and Spadina Station

Top-rated holiday rentals in The Annex, Old Toronto

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The exterior of a tall, modern building is captured from a low angle, highlighting its sleek design and illuminated upper floors. A bronze sculpture of a horse stands prominently in front, set against expansive glass walls reflecting city views.
Flat in Yorkville
4.89 out of 5 average rating, 112 reviews

Sweet Home in Yorkville, Toronto, free parking

Welcome to your home at Yorkville Plaza in the heart of downtown Toronto! Formerly the Four Seasons Hotel Condo, this suite has been newly furnished. The main bedroom is full of natural light and the den serves as a second bedroom or office. The living room sofa can be turned into a huge bed. You can sit beside fireplace or cook in the kitchen; you can watch spectacular city views or enjoy comforts from smart TV to smart toilet. Walking around in the historical old Yorkville Village is joyful!

Top guest favourite
Apartment in Downtown Toronto
4.96 out of 5 average rating, 170 reviews

Beautiful Petit Gem Ap. In Downtown! Walk Anywhere

Welcome to our lovely petit aparment in heart of downtown Toronto! Our place has everything you might need in order to enjoy the city, work remotely and have a great time when the weather outside is not the best! Located right in downtown, you can basically walk anywere fast: Eaton Centre, Dundas Square, U Toronta, etc. Enjoy many of the high end stores located in the area and also some of the best restaurants! The entire place is sensitized using UV lights and COVID 19 cleaning solutions.

Top guest favourite
A bright living room is filled with natural light, featuring a cozy couch and two large cushions arranged on the floor. A round coffee table sits at the center, adorned with decorative objects. Green plants add a touch of nature, complemented by light, airy curtains.
Flat in Midtown
4.97 out of 5 average rating, 68 reviews

Sundrenched 1BR Downtwn Apt-Views & Free O/N Prkng

THE ANNEX OASIS Unwind on a rainforest-inspired balcony with stunning downtown views—steps from cafes, shops & UofT. Perfect for World Cup fans! Our spacious 1-BD home blends comfort, charm & location. ➜ 3-min walk to St. George Subway & UoFT (easy access to matches) ➜ Free overnight street parking ➜ Breakfast snacks, coffee & tea ➜ Workstation with screen + high-speed WiFi ➜ 60" Home Theater for post-match replays ➜ Balcony sunsets & wine after a big game Your ideal homestay in Toronto.

Guest favourite
Apartment in Downtown Toronto
5.0 out of 5 average rating, 15 reviews

Cozy 1BR+den in the Annex | Steps to subway

Discover the charm of the Annex in our bright 1BR+Den, steps from Bathurst Station. This quiet retreat features high ceilings, a balcony with stunning city views, and sleeps 4 comfortably. The den is a perfect home office or dining nook. You’re surrounded by Toronto’s best cafes and independent boutiques, blending historic vibes with modern comfort. Whether you’re here for work or a city getaway, enjoy a peaceful, stylish home base in the heart of it all! STR-2507-FKFFBP

Top guest favourite
A modern living area is highlighted by a sleek sofa and a glass coffee table atop a zebra-patterned rug. An open layout reveals a kitchen area equipped with contemporary appliances. Art pieces adorn the walls, and a smart TV is mounted for entertainment.
Flat in Yorkville
5.0 out of 5 average rating, 84 reviews

The One in Yorkville-Previously Four Seasons Hotel

Our 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 favourite
A spacious living area features exposed brick walls and high ceilings. A light-colored curved sofa is positioned around a round coffee table, enhancing comfort. Natural light pours in through large windows and a skylight, creating an inviting atmosphere. The area is accented by tasteful artwork.
Loft in Midtown
4.98 out of 5 average rating, 66 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.

Guest favourite
A spacious living room features a white sectional sofa and a contemporary coffee table on polished wooden floors. Natural light enters through large windows, complemented by a decorative brick fireplace and lush green plants. A ceiling fan enhances airflow in the inviting space.
Home in Midtown
4.85 out of 5 average rating, 97 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 .

Top guest favourite
A dining area is presented with a wooden table set for meals. A textured vase holds an arrangement of greenery and foliage. Black-framed photographs adorn the wall, creating an artistic backdrop, while a pendant light offers soft illumination.
Flat in Midtown
4.97 out of 5 average rating, 111 reviews

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

Superhost
Flat in Midtown
4.75 out of 5 average rating, 64 reviews

Spacious 1 Bed w/ Patio Walk up by Subway

Stay in one of Toronto's most sought-after neighborhoods. This 1-bedroom suite with a spacious private patio offers the perfect balance of comfort, convenience, and location. Just steps from Bathurst & Bloor Subway Station, you'll be minutes from downtown, U of T, Kensington Market, Yorkville, Queen Street West, and Toronto's top restaurants, cafés, and nightlife.

Guest favourite
A modern living area is showcased with a plush blue sofa, accented by decorative cushions. A marble coffee table is centered on a patterned rug, while a large flat-screen TV is mounted on a wooden console. The expansive windows offer views of the cityscape.
Apartment in Yorkville
4.83 out of 5 average rating, 70 reviews

Bright Condo in Yorkville

Welcome to the heart of Yorkville! Enjoy your stay at our spacious 2 bedroom condo and make yourself feel at home. At this location you will be surrounded by the finest Dining , Luxury Retail Stores, Museums' , University Of Toronto, Parks, and walking distance to TTC Station. Large Bay Windows, faces North, with beautiful city views and breathtaking sunsets.

Guest favourite
The living room features a spacious leather sectional sofa facing a central coffee table. Natural light fills the area through multiple large windows. A brick fireplace adds warmth, while a staircase with glass railing leads to the upper levels. Potted plants bring a touch of greenery.
Home in Midtown
4.88 out of 5 average rating, 270 reviews

Bright, Stunning Victorian Townhouse in the Annex

Newly renovated, 3 level, 2-bedroom sun-filled unit, situated in the Annex. Brick fireplace, 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 and Spadina Subway, Casa Loma, Yorkville, University of Toronto, and museums.

Top guest favourite
A spacious outdoor deck is furnished with a large sectional couch and a glass table. The well-maintained garden is bordered by wooden fencing, featuring a lush green lawn, flowering plants, and a hammock hung between two trees, with a children's playhouse visible in the background.
Flat in Midtown
4.98 out of 5 average rating, 99 reviews

Main fl Annex, private garden oasis, welcome dogs!

Entire main floor of a beautiful 100-year-old Victorian house with incredible 100-foot-long PRIVATE garden oasis - great for dogs!. Located in the heart of the Annex, one of Toronto’s oldest and most vibrant neighbourhoods with stately homes, leafy streets and loads of hip bars, cafes, and restaurants.

Popular amenities for The Annex, Old Toronto holiday rentals

  1. Airbnb
  2. Canada
  3. Ontario
  4. Toronto
  5. The Annex