
Holiday rentals in The Annex, Old Toronto
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Top-rated holiday rentals in The Annex, Old Toronto
Guests agree: these stays are highly rated for location, cleanliness and more.

High-End Prime Fashion District
Gorgeous modern studio located in the heart of downtown hi-end fashion district - Yorkville. You'll stay in the middle of Toronto's main luxury shopping hub with Cartier, Versace, Chanel, Gucci, LV, D&G, and many more. With an array of upscale dining options, cultural attractions, and entertainment venues nearby, you'll find anything you crave for. It's at the crossing of main streets Yonge and Bloor, providing a convenient access to 2 main subway lines to take you anywhere. Fully equipped.

Chic Yorkville 1BD W/ Private Terrace
CHIC 1-bedroom condo in the heart of Yorkville, Toronto. At your doorstep are bustling streets, charming cafes, Michelin-star restaurants, upscale boutiques, art galleries, ROM, and Whole Foods. The space has the perfect balance of elegance, convenience, and comfort. Stocked with essentials, and a rare 100 sq ft private terrace. Savor your morning coffee or an evening glass of wine (or bottle!) As the owner, I personally oversee every detail to ensure cleanliness and comfort for your arrival.

Luxury Condo - Yorkville Toronto
Enjoy a stylish and luxury experience at this centrally located place in the Heart of Yorkville. Walking distance to Queen's Park, Royal Ontario Museum, University of Toronto, Whole Foods, Yorkville Village Shopping and more! Steps away from world-class dining including Cibo Wine Bar, Dimmi Bar and Trattoria, Kasa Moto, PLANTA, Sassafraz, STK Steakhouse, and Yamato Japanese Restaurant. Upscale boutiques including Chanel, Gucci, Holt Renfrew, Louis Vuitton, Prada, Tiffany & Co., and many more!

Cozy 2BR in DT Toronto with Parking+Laundry
Enjoy classic Toronto living in this bright and spacious 2-bedroom, 2-bath apartment in The Annex, just steps from Bloor Street’s vibrant cafés, restaurants, and boutiques. ***We block off the entire home for guests who only need 1-bedroom for maximum privacy & value. Walk to the UofT, Casa Loma, the ROM, or hop on the nearby Spadina or Bathurst subway. Enjoy a fireplace, balcony, fully equipped kitchen, in-unit laundry, and parking - your stylish home for an extended Toronto stay.

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.

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.

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.

Sundrenched 1BR Downtwn Apt-Views & Free O/N Prkng
THE ANNEX OASIS Unwind on a lush, rainforest-inspired balcony with sweeping downtown views - steps from cafes, trendy shops & restaurants, culture & UofT. Our spacious 1-BD home in Annex blends comfort, charm & location. ➜ 3-min walk to St. George Subway & UoFT ➜ Free overnight street parking ➜ Complimentary breakfast snacks, coffee & tea ➜ 2 workstations+high-speed WiFi ➜ 60" Home Theater Smart TV ➜ Beautiful sunsets from balcony Your homestay in Toronto.

Admire City Views from Bed at this Chic Apartment
The critics have spoken! This five star rated,professionally designed unit is fresh and functional . The art work and accessories were carefully chosen to accentuate your positive living experience. This is a one bedroom, one bathroom unit with kitchen living dining and den areas. There is a fully equipped gym on the 3rd floor for your use. Check in time is between 3 PM and 10 PM the day of arrival and check out time is 11 AM the day of departure.

Luxury Lakeview | Downtown | Sleeps 6 | Parking
Welcome to your luxury escape in the heart of Downtown Toronto! Walking distance from Toronto’s most famous landmarks, CN Tower, Rogers Centre, and Scotiabank Arena. In a prime location, most concert, events & venues are held nearby. You’ll be surrounded by a selection of top restaurants & nightlife, making it easy to experience the best of the city! You will have panoramic views of the lake and skyline, showcased through floor-to-ceiling windows!

Cozy Annex Home
Our cozy one-bedroom condo is in a quiet building just steps from Bathurst Station and Bloor Street. We love how the space feels bright and open with its high ceilings and large windows, yet still warm and relaxing after a busy day in the city. We love how close we are to great cafes, parks, and neighbourhoods, and hope you will feel right at home while exploring Toronto.

Exclusive Studio in Yorkville
The perfect location to explore Toronto! This beautiful condominium is located in one of downtown Toronto’s most luxurious neighbourhoods, Yorkville. Close to an abundance of restaurants including Michelin star restaurants, high end shops, entertainment, public transit and so much more. The previous Four Seasons Suite is now ready to be your home away from home.
Popular amenities for The Annex, Old Toronto holiday rentals
Other great holiday rentals in The Annex, Old Toronto

Boutique 1BR + Sofa Bed in coveted Yorkville!

Ultimate Toronto Escape – Stylish & Vibrant

Chic, Centrally Located 1 Bedroom Suite

Charming, Bright Victorian Townhouse in the Annex

Your Private Christie Pits Hideout

Premiere 1 Bedroom Suite

Downtown Life with Stunning Views + 1 Free Parking

Panoramic City Views | Pool, Hot Tub & Gym Perks
When is the best time to visit The Annex, Old Toronto?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £55 | £52 | £55 | £54 | £59 | £63 | £64 | £66 | £64 | £63 | £62 | £66 |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
Quick stats about holiday rentals in The Annex, Old Toronto

Total holiday rentals
Explore 300 holiday rentals in The Annex, Old Toronto

Verified guest reviews
Over 10,120 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wifi availability
290 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

4.7 Average rating
The Annex, Old Toronto stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
The Annex, Old Toronto’s top spots include Royal Ontario Museum, Bata Shoe Museum and Spadina Station
Destinations to explore
- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Nike Square One Shopping Centre
- BMO Field
- Harbourfront Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Financial District
- Massey Hall
- Niagara Falls State Park
- Casa Loma
- Dufferin Grove Park
- Lakeridge Ski Resort
- Toronto City Hall
- Casino Niagara




