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
An open living space is visible, featuring light-colored walls and wooden flooring. A large moose head mount decorates the wall, adding a unique focal point. Two barstools are positioned at a kitchen counter, with kitchen appliances discreetly arranged in the background.
Apartment in Church-Wellesley
4.96 out of 5 average rating, 163 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 cozy living area features a grey sofa and two matching armchairs, all positioned on a neutral area rug. A modern arc floor lamp provides soft lighting, while framed art adorns the walls. A small glass side table sits beside the sofa, enhancing the space's functionality.
Flat in Midtown
4.93 out of 5 average rating, 227 reviews

Cute Private Apartment near University of Toronto

This cozy main floor apartment with private walk out patio, located on a quiet street in the beautiful Annex neighbourhood. Free parking Laundry in building Shared backyard 5 minute walk to subway (Christie Station) 5 minute walk to Bloor Street, the restaurants and bars of Korea Town, and historic Christie Pits Park. Walking distance to University of Toronto and George Brown College Casa Loma campus. There are a lot of great restaurants, bars and local grocery stores within a short walk.

Guest favourite
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.
Flat in Annex
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 favourite
A modern living area features a sleek brown leather couch with decorative pillows, positioned across from a dark wooden coffee table. Bright natural light enters through large bay windows, complemented by light-filtering curtains. A decorative wall map and a large green plant add character to the space.
Home in York
4.99 out of 5 average rating, 204 reviews

Welcome to Greenhills, a Charming Home w/ Parking

Clean Open Concept, Sun-Filled 2 Bedroom main floor home with PARKING; Can sleep up to 4 people. Featuring simple modern décor, queen size beds, big beautiful windows with room darkening curtains, closet storage. Dedicated office desks in bedrooms Full kitchen, with oil, seasoning spices, toaster, hot water kettle, Keurig Coffee Machine and complimentary coffee+tea. Clean bathroom with shampoo+conditioner+body wash+lotion SMART TV 60” Fast internet Wifi Check-In: 3PM Check-Out: 11AM

Guest favourite
A cozy sleeping area is presented with a spacious bed, featuring soft bedding and decorative pillows. Nightstands flank the bed, providing small plants and ambient lighting. A calming nature print is displayed above the bed, enhancing the serene environment.
Home in Midtown
4.86 out of 5 average rating, 105 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 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, 202 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.

Guest favourite
The exterior of a charming three-story house is depicted, featuring a wooden porch with a railing. The facade combines dark brick and light grey siding, while large windows allow natural light to enter. A small garden area is visible in front, enhancing the welcoming entrance.
Home in Wychwood
4.89 out of 5 average rating, 107 reviews

Luxurious 2 Bedroom in the heart of the city!

Spacious, renovated 2 bedroom space and a 4 piece washroom. It is a beautiful Basement space located in a family home in a family-friendly quiet Toronto area that is close to Wychwood Barns Park (featuring Saturday open market) Casa Loma, Christie Pits Park. Features: Spacious open concept kitchen and dining-living equipped all facilities to make the guest stay comfortable. Primary bedroom setup for WFH Desk. At doorstep TTC bus services and paid street parking available.

Guest favourite
A modern living area features a sectional sofa with decorative pillows, accompanied by a glass coffee table on a round, plush rug. Large windows provide ample natural light, and a sleek kitchen with stainless steel appliances and dark cabinetry creates an open and inviting layout.
Apartment in Harbourfront
4.88 out of 5 average rating, 113 reviews

Gorgeous Downtown Condo

Gorgeous high-ceiling condo in downtown Toronto, located in the vibrant old fort york neighborhood. Spacious and bright unit with 2 bedrooms, 2 bathrooms, and 2 balconies. Equipped for remote work with 2 desks. A step away from the city best-known attractions: Lakefront, CN Tower, Rogers Center, Aquarium, shops, bars, restaurants and nightclubs Easy access to commodities (5 min walk from Starbucks, LCBO, Lowblaws, CityAirport and TTC) Underground parking spot is included.

Top guest favourite
Apartment in Annex
5 out of 5 average rating, 10 reviews

Cozy Home in The Annex | Bright 1BR+Den | Sleeps 4

Welcome to our cozy one-bedroom condo in a quiet building steps from Bathurst Station and Bloor St. We love the bright, open feel with high ceilings, large windows, and an amazing unobstructed city view from our balcony. Our home sleeps up to four guests with a cozy bed and a living room sofa bed. The den features a dining table perfect for eating or working. We love being so close to great cafes and parks, and hope you feel right at home while exploring Toronto!

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 Annex
4.88 out of 5 average rating, 263 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 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, 221 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.

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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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