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 stylish living area features a leather sofa and an accent chair, creating a cozy seating arrangement. A modern coffee table is positioned centrally, with a small plant and decorative items. The open kitchen area includes sleek cabinetry and a microwave, enhancing the contemporary design.
Apartment in Yorkville
4.99 out of 5 average rating, 84 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 suite.

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
The image captures a compact bedroom featuring a spacious bed dressed in a patterned burgundy cover. A comfortable rocking chair sits beside the bed. In the background, light filters through a window covered with sheer curtains, and wooden cabinetry offers additional storage.
Home in North York
4.83 out of 5 average rating, 12 reviews

Private Bedroom, Bathroom, Kitchen -Basement Apt

Take a break and unwind at this peaceful oasis. This is a rare gem as the bedroom, bathroom and kitchen are all private, for an affordable price. It is very simple and some of our personal belongings are in the space but we keep the price low to make up for it. Most rentals in this area of Toronto have shared bathroom or kitchen or are very expensive. Within walking distance to Parkway Mall. 5 minute drive to the 401 or DVP which will take you to downtown Toronto in 25 minutes (if no traffic).

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
4.83 out of 5 average rating, 24 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.

Superhost
A modern living space features large windows that overlook the city skyline. Stylish furnishings include a spacious couch with decorative pillows, yellow dining chairs at a glass table, and a sleek kitchen with a dark countertop. Natural light brightens the open layout.
Flat in Yorkville
4.9 out of 5 average rating, 20 reviews

Beautiful 1BR Condo Coveted Yorkville!

Welcome to our stylish and luxurious Yorkville condo! Immerse yourself in the heart of Toronto's most upscale neighbourhood, surrounded by top-rated shopping, renowned restaurants, and cultural attractions. This chic retreat offers modern amenities, elegant design and a prime location for an unforgettable stay in a newly-constructed building. ➜ Approx. 500ft² / 56m² of space ➜ Highspeed WIFI ➜ In-unit washer & dryer ➜ Fully equipped kitchen ➜ Steps to Bay & Museum subway stations

Superhost
Flat in Toronto

Modern 2-BD Apartment in Prime Toronto

Experience contemporary living in the heart of Yorkville with this bright, thoughtfully arranged Suite. It offers one private bedroom, an additional den bed, and two well-designed bathrooms. The space features elegant finishes, premium Miele appliances, a wine fridge, a Nespresso machine, and in-suite laundry. With room for up to four guests, it also includes a private balcony with city views—just steps from top dining, boutique shops, and major Toronto attractions.

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
A spacious living area is featured with a dark sectional sofa adorned with textured cushions. A round coffee table, topped with a decorative bowl and books, complements the soft area rug beneath. Natural light filters through large windows, illuminating the neutral walls and decor.
Flat in Wychwood
4.94 out of 5 average rating, 72 reviews

Modern 1-Bedroom Loft

Experience the city like a local in this unique professionally designed space. This large, bright, airy space boasts 14 ft ceilings and has in-suite heating and AC. 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

Guest favourite
Flat in Yorkville
5 out of 5 average rating, 8 reviews

Chic Yorkville Condo • Sleeps 3 • Prime Location

Experience upscale city living in the heart of Yorkville. This stylish brand-new 1-bedroom condo offers modern finishes, luxury Miele appliances, and a fully equipped kitchen — perfect for business travelers, couples, or small families. Nestled in one of Toronto’s most desirable new developments, you’ll be steps from world-class dining, high-end shopping, and the best of downtown.

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.

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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