Holiday rentals in The Annex, Old Toronto

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Top-rated holiday rentals in The Annex, Old Toronto

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Guest favourite
A modern living space features a green sofa paired with yellow accent chairs. Large windows provide a view of the city skyline. A kitchenette is visible, showcasing sleek cabinetry and a countertop. Natural light brightens the room, highlighting the cozy decor.
Apartment in Yorkville
4.88 out of 5 average rating, 129 reviews

Scenic View! Luxury entire condo/Toronto Downtown

This unit has amazing view & Great location Luxurious area in Toronto Yorkville ! Everything is near by. Walking distance U of T campus, Royal Ontario Museum, HI-END shopping malls , restaurants and subway -1bedroom + Den -Queen bed + 2 sofa bed -High speed wifi -SmartTV (Access to Netflix or YouTube) -Cable TV -All in one Printer (Wireless) -Fully equipped kitchen (no oven) -Washer + Dryer -Iron+Ironing board -Bidet seat equipped on toilet -Gym -Paid Parking is available in the building

Superhost
A panoramic view of the city skyline is displayed through large bay windows. The scene features various buildings under construction, showcasing a blend of modern architecture and urban development. The sky is partly cloudy, allowing natural light to illuminate the space.
Apartment in Yorkville
4.62 out of 5 average rating, 55 reviews

1BR Condo Modern Living

Experience luxury in this 430 sq ft one-bedroom suite on the 28th floor in Yorkville. Features include a fully equipped kitchen, in-unit washer & dryer, premium high-speed WiFi, and paid parking upon request. The suite offers contactless check-in. Walk score: 98, Transit score: 96, Biker score: 95. Just 27 mins to Pearson Airport, 9 mins drive to CN Tower and Scotiabank Arena, and 4 mins walk to the Royal Ontario Museum. Enjoy modern urban living in a prime location! 🎈Check in time ends at 8pm,

Top guest favourite
The living area features a modern sofa facing a flat-screen TV, with a decorative coffee table set beside it. A sleek kitchenette is visible in the background, equipped with stylish cabinetry and appliances. Sunlight streams through large windows, illuminating the space.
Flat in Yorkville
4.98 out of 5 average rating, 53 reviews

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.

Guest favourite
A spacious living and dining area features a light-colored sectional sofa adorned with a red plaid throw. Modern artwork decorates the white walls, complemented by a wooden coffee table and comfortable armchairs. Natural light streams through windows, enhancing the warm hardwood flooring throughout the space.
Home in Annex
4.84 out of 5 average rating, 25 reviews

Peaceful 3BR House • Central Spot • Outdoor Space

✦ This stylish 2-level, 3-bedroom home is in a quiet, central neighbourhood—offering a perfect blend of comfort and convenience. Inside, you'll find three bright and cozy bedrooms, a modern bathroom, a fully equipped kitchen, and spacious living and dining areas. Step out to the private backyard, complete with comfy seating and lush greenery. Enjoy high-speed WiFi, laundry, and a dedicated parking spot. Walk to local cafes, parks, and transit—ideal for families, professionals, or longer stays.

Top guest favourite
Flat in Yorkville
4.95 out of 5 average rating, 44 reviews

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!

Guest favourite
Home in Toronto
5 out of 5 average rating, 5 reviews

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.

Guest favourite
A stylish living space features an eye-catching geometric wallpaper, complemented by a contemporary wooden sideboard and a gray sectional sofa. A small round table and a two-person bar table are positioned near large windows that offer expansive city views.
Apartment in Yorkville
4.93 out of 5 average rating, 196 reviews

Beautiful 1 Bedroom Yorkville Condo (IG-hotspot)

Pamper yourself with everything Yorkville has to offer with this professionally decorated, NYC inspired condo at the heart of Toronto's most exclusive address with complimentary valet parking. Queen size bed, sofa bed in living room, 2 person bar table, work station and a 55" Smart TV to accommodate all your needs. Contemporary art by local artist throughout with high end furniture and Miele appliances. South facing lake/city views through expansive floor to ceiling windows.

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 out of 5 average rating, 73 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 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 Annex
4.98 out of 5 average rating, 49 reviews

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.

Top guest favourite
Apartment in Mirvish Village
5 out of 5 average rating, 9 reviews

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.

Top guest favourite
A modern living area features a spacious gray sectional sofa adorned with colorful throw pillows. Abstract artwork is displayed on the walls, while a round coffee table holds snacks. A large window allows natural light to fill the room, with a view of greenery outside.
Home in Annex
5 out of 5 average rating, 218 reviews

Annex Garden Coach House

Welcome to the Annex Garden Coach House! Well suited for solo and family travellers alike, seeking a centrally located, quiet little house, surrounded by backyard trees, in the leafy Annex neighbourhood. You're able to park for free at your private front door, and it's a quick walk to your choice of three nearby subway stations.

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 Annex
4.98 out of 5 average rating, 88 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

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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 Royal Conservatory of Music

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