Vacation rentals in The Annex, Old Toronto

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in The Annex, Old Toronto

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

1 of 1 pages1 / 1
Top guest favorite
Condo in Yorkville
4.9 out of 5 average rating, 313 reviews

Luxury Yorkville Escape | Condo in Prime Location

Discover refined living in this beautifully furnished apartment in Yorkville Toronto’s most glamorous & exclusive neighborhood. With new furniture & modern appliances, this space blends comfort with sophistication. Step outside and find yourself surrounded by luxury boutiques, acclaimed restaurants, chic cafes, & world-class art galleries. With Bay subway station just a 3 minute walk away, the entire city is at your fingertips. Elevate your lifestyle in a place where elegance meets convenience.

Top guest favorite
A modern two-story cottage features a sleek exterior with a combination of wood and green siding. Symmetrical windows offer natural light, while a covered entryway with a wooden deck leads to two separate entrances. Lush greenery surrounds the home, enhancing its private setting.
Guest suite in Toronto
4.95 out of 5 average rating, 220 reviews

Cozy small newly built Toronto Islands getaway

Escape to a modern cottage on Toronto Island Looking onto Lake Ontario is our newly constructed modern home. Enjoy our cozy private guest suite in our family home with a kitchenette, ensuite bathroom, and private entrance Just a quick ferry ride from the bustling downtown core come explore the Toronto Islands which is the biggest car-free community in North America; with beaches, trails & skyline views as well as an amusement park in the summer. We also have 2 bikes you can use to explore.

Guest favorite
A warm and inviting living area features exposed brick walls and a large wooden dining table surrounded by black chairs. Soft lighting from a vintage chandelier casts a gentle glow over a cozy sofa and a stylish entertainment unit, creating a sense of comfort.
Apartment in Midtown
4.94 out of 5 average rating, 118 reviews

Luxurious Annex/Yorkville 1300 Sq Ft & Parking

Beautifully appointed, top quality furnishings & amenities , spacious Yorkville/Annex rental. Full 1300 sq foot. apartment located within a Heritage Victorian Brownstone! Exceptionally located, walking distance to subway, restaurants and all the sights! Walk to Casa Loma, Royal Ontario Museum & Yorkville. Parking, Wifi, Chromcast, Fibe TV, Local High Def TV included. Fully equipped gourmet kitchen. Air Conditioned. Digital safe for valuables. Treat yourself to pantry snacks, coffee & tea.

Top guest favorite
Home in Downtown Toronto
4.99 out of 5 average rating, 248 reviews

Stylish 1870s Home near Distillery District & Old Toronto

Visiting for fifa? Stop here...Steps from the Distillery District downtown, this Top rated listing is a beautifully restored 1870s row-house (townhouse) that blends historic charm with modern refinement. Thoughtfully designed throughout, it’s located downtown also close to St. Lawrence Market, and some of the city’s best cafés and restaurants. In the evening, unwind in the serene, charcoal-toned bedroom beneath the warm glow of a statement chandelier—your refined Toronto retreat awaits

Guest favorite
Apartment in Midtown
4.85 out of 5 average rating, 109 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.

Top guest favorite
A bright bedroom features a spacious bed adorned with plush pillows in pink stripes. Large windows provide stunning views of the cityscape, while dark curtains offer options for privacy and light control.
Condo in Yorkville
4.99 out of 5 average rating, 196 reviews

Admire City Views from Bed at this Chic Apartment

The critics have spoken! This five-star rated, professionally designed unit offers a fresh, functional, and beautifully curated living experience. Every piece of artwork and each accessory has been thoughtfully selected to enhance comfort, style, and positive energy throughout the space. This spacious one-bedroom, one-bathroom suite features a fully equipped kitchen, open living and dining areas, and a versatile den — perfect for working remotely or relaxing after a day in the city.

Guest favorite
Home in Midtown
4.86 out of 5 average rating, 108 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.

Guest favorite
Condo in Downtown Toronto
5 out of 5 average rating, 12 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

Guest favorite
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.
Condo in Yorkville
4.93 out of 5 average rating, 208 reviews

Beautiful 1 Bedroom Yorkville Condo w/ Parking

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.

Guest favorite
A glass table is positioned near large windows, offering an unobstructed view of the city skyline. Two modern chairs are placed around the table, with a small potted plant and a decorative item enhancing the scene. The background features tall buildings and hints of greenery.
Condo in Yorkville
4.89 out of 5 average rating, 173 reviews

Steps to Four Seasons Hotel Yorkville Condo

Unobstructed panoramic view in the heart of upscale Yorkville. Minute walk to Bay subway station, Whole Foods, ROM and U of T and high-end restaurants. Easy parking @ 74 Yorkville for $20 (daytime). Around the corner from Toronto's main luxury shopping hub, Yonge + Bloor. *Upscale neighborhood *Highspeed WIFI *Walk score of 96 *Transit score of 93 *Bike score of 98 (rentable Bixi bikes nearby) *Fully equipped kitchen *Full-sized washer/dryer *Gym in building

Guest favorite
An impressive view of a modern high-rise building is captured from below, showcasing the architectural details of the glass façade and concrete structure. A bronze statue stands prominently at the base, adding a cultural element to the urban landscape.
Condo in Yorkville
4.9 out of 5 average rating, 182 reviews

Yorkville Toronto Breakfast Included

Entire apartment is yours to enjoy. I am the owner: I always clean-this is not multi operated. Laundry is carefully cleaned. New leather reclining sofa. I include breakfast groceries at no charge. Coffee, tea, milk, 2 apples, 2 oranges, 2 bananas, 4 bagels, cream cheese, strawberry jam, dozen eggs, butter, onion, tomatoes. Walk to Whole Foods, Starbucks. University.50" TV + 32 " TV, includes NETFLIX, AMAZON PRIME VIDEO, INTERNET.

Guest favorite
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, 264 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.

Popular amenities for The Annex, Old Toronto vacation rentals

When is the best time to visit The Annex, Old Toronto?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$18,200 GYDG$19,037 GYDG$18,200 GYDG$15,481 GYDG$16,945 GYDG$17,991 GYDG$18,200 GYDG$18,828 GYDG$18,410 GYDG$17,991 GYDG$17,782 GYDG$18,828 GYD
Avg. temp-3°C-3°C2°C8°C14°C20°C23°C22°C18°C11°C5°C0°C

Quick stats about vacation rentals in The Annex, Old Toronto

  • Total vacation rentals

    Explore 290 vacation rentals in The Annex, Old Toronto

  • Verified guest reviews

    Over 10,190 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wi-Fi availability

    290 of The Annex, Old Toronto vacation rentals include wi-fi 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

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