House holiday rentals in The Annex, Old Toronto

Find and book unique houses on Airbnb

Top-rated house rentals in The Annex, Old Toronto

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

%{current} / %{total}1 / 1
Guest favourite
A bed is adorned with a blue bedspread and decorative pillows featuring intricate patterns and vibrant colors. The focal pillow displays a colorful geometric design, creating a cozy and inviting look.
Home in Christie Pits
4.83 out of 5 average rating, 137 reviews

Cozy Zen Space| Private Entry|Downtown+Subway|Yoga

Private space, separate entrance, downtown Toronto, 5-min walk to Bloor Street. Walk to restaurants, cafes, patios, comedy clubs, and Christe Pitts. Saturday morning farmers market nearby. Easy access to U of T, TMU, with the subway, plus city bikes and Uber. Features a comfortable queen bed, quiet vibe, and spacious private bathroom. Kitchenette. Guests also have access to a Peloton bike and yoga studio behind the house—perfect for relaxing or staying fit during your visit. STR-2111-HRQXVL

Top guest favourite
A modern kitchen area features smooth gray cabinetry and stainless-steel appliances. A wooden table is set for dining, with simple dinnerware arranged on top. A plush brown sofa is positioned nearby, complemented by decorative elements on the wall and a stylish clock.
Home in Wychwood
4.95 out of 5 average rating, 132 reviews

Amazing 1BR Suite Near Downtown!

A private one bedroom luxury basement suite in popular Wychwood has it all: amazing kitchen; open living area with oversized sofa - watch Netflix or cable on the wide-screen TV; dine at a reclaimed wood table; sleep great on a queen size Sealy Posturepedic mattress in the bedroom, 8ft ceilings, private entrance; new washer/dryer! Public transit is steps away. Visit famous Wychwood Barns or shop on St. Clair West - less than 10 min walking. High speed unlimited wifi, premium cable TV, and more!

Top guest favourite
A spacious sleeping area is highlighted by a comfortable bed adorned with patterned bedding. A bright seating area features a vibrant red couch and a blue chair, complemented by natural light from large windows. A flat-screen TV stands on a modern media console.
Home in Bedford Park
4.91 out of 5 average rating, 183 reviews

Uptown Separate Bright Suite ( Free Parking )

Great private and quiet bright furnished basement suite(just 6 steps under street level) with separate entrance in a classy and safe Bedford Park neighborhood in central Toronto,12 min walk to Lawrence subway station,2 min to bus station,3 min to Loblaws(best Canadian grocery store), 2 min walk to Yonge street with shops, bars and the best restaurants ,18 min drive to Pearson int airport and tennis courts nearby. Our place is perfect for couples, solo adventurers and business travelers.

Top guest favourite
A bright living room is highlighted by a cozy sofa and a sleek coffee table. Two yellow chairs face large windows, allowing natural light to fill the space. A flat-screen TV is mounted on the wall, and a decorative plant adds a touch of greenery.
Home in Roncesvalles
4.99 out of 5 average rating, 174 reviews

Luxury modern Victorian - private parking included

This recently renovated gem has all of the comforts of home, with a fully appointed kitchen that has everything you need to cook a great meal. Nespresso coffee and a selection of teas are also included. Two Smart TVs and a Bluetooth speaker for entertainment. Two comfortable beds and a spacious spa bathroom will make your stay feel like home. A work remote work set up is available for those who require it. The private backyard includes a gas BBQ and private parking is included.

Top guest favourite
An outdoor seating area is showcased, featuring a comfortable couch adorned with patterned cushions. Flanking the couch, two red chairs face a wooden fence, while a decorative lantern and potted plants add touches of greenery, highlighting the inviting atmosphere of this private space.
Home in Cabbagetown
4.94 out of 5 average rating, 588 reviews

Comfy Oasis In Historic Downtown Neighborhood

According to Airbnb, we are "One of the most beloved homes on Airbnb". Now in the top 5% of all listings on AIRBNB. Superhosts for 10 years! This renovated guest house features an open-plan kitchen, a spiral staircase to a beautiful and open loft suite, with custom furniture and decorating accessories (1 bed + 1 sofabed). Enjoy the beautiful garden in the summer, and sip any of the more than 15 different complimentary teas and coffees we offer. This guest house is FULLY equipped.

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 Annex
4.87 out of 5 average rating, 102 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.

Top guest favourite
The living area features a modern design with a comfortable sofa accented by patterned pillows. A marble dining table is surrounded by elegant chairs. A striking chandelier hangs above, while a large round mirror reflects the ambient light from windows dressed in soft curtains.
Home in Corktown
4.99 out of 5 average rating, 238 reviews

Stylish 1870s Home near Distillery District & Old Toronto

“Rated a Top 10 listing by BlogTO and frequently featured as a must-stay in Toronto. Love thoughtful details? You’ll find them here in this stylishly remodeled 1870s rowhouse. Start your day at St. Lawrence Market, wander through the pedestrian-friendly Distillery District, and explore nearby cafés, restaurants, and bars. In the evening, retreat to the plush, charcoal-hued bedroom and drift off under the glow of a tiered Restoration chandelier. The perfect Toronto stay awaits.”

Top guest favourite
A cozy living area features a grey sofa adorned with colorful cushions, complemented by a glass coffee table sitting on a softly patterned rug. Two wooden chairs provide additional seating. Natural light filters through a nearby window, highlighting the hardwood floors.
Home in University
4.82 out of 5 average rating, 184 reviews

Two story home & garden in vibrant neighbourhood

Newly renovated heritage home in the heart of one of Toronto's most vibrant neighborhoods. Perfect for families, the home features hardwood floors, lots of natural light, and very comfy beds. Conveniently located steps from the subway on a residential street, you are close to many great restaurants & blocks from the U of T and Kensington market. Not far from Scotiabank arena & Rogers centre - for concerts and sporting events. Patio and garden are yours to enjoy. Pets welcome.

Guest favourite
An inviting sleeping area is highlighted by a spacious bed with neatly arranged pillows. A stylish lamp provides warm lighting, while a full-length mirror is positioned beside the wall. A cozy throw blanket is draped over the bed, and a magazine rests on the bedside table.
Home in York
4.83 out of 5 average rating, 200 reviews

Cozy and Chic Gem in the City

Entire lower level unit. Very clean and cozy unit in a great friendly neighborhood. The unit is bright and airy. The bathroom and kitchen is yours to use. Separate entrance through the side door of the house. Closet space to store your luggage and clothes. Coffee machine with pods and kettle are at your disposable. Extra blankets and pillows are available upon request. While the unit offers a private setup, the main house may also be accessed or shared as per your needs.

Guest favourite
The inviting bachelor suite features a spacious bed with neutral-toned bedding, complemented by folded towels. A kitchenette is visible in the background, along with modern appliances. Soft lighting enhances the calm ambiance, while stairs are seen leading to the exterior.
Home in Garden District
4.97 out of 5 average rating, 102 reviews

Pembroke Hideaway

Pembroke hideaway is your prime downtown privacy with high end finishes, full kitchen with fridge, stove, microwave, dishwasher and all the essentials. Full walk-in bathroom and shower with laundry facilities in the suite. Ultimate privacy with a separate entrance in a secure property. Walking distance to practically anything in the city. Brand new renovation top to bottom in 2022. Comfort, convenience and Luxury!

Top guest favourite
A bright and airy living space showcases two red sofas facing a modern coffee table, with a television mounted on the wall. A cozy wood stove is visible in the corner, with exposed brick adding texture to the room. Large skylights allow natural light to fill the area.
Home in Palmerston
5 out of 5 average rating, 102 reviews

The Peony Loft - a Modern Take on the Victorian

Built in 1893, this classic Toronto Victorian home will be a relaxed introduction to city life. Enjoy the upper living space, laid out over two floors, with a gorgeous private, beautiful furnished sky deck with a view of Toronto's exciting skyline. Experience the restaurants, pubs & nightlife of Toronto's College St. neighbourhood of Little Italy, all within walking distance of your front door.

Top guest favourite
The exterior of a detached heritage home is showcased, featuring a brick façade and large windows. The entrance is framed by vibrant orange flowers and lush greenery. A yellow awning extends over the front door, adding a cheerful touch to the welcoming ambiance.
Home in Church-Wellesley
4.92 out of 5 average rating, 136 reviews

Heritage House all to Yourself! 1BR 3BA 2 Liv Rms

Beautiful detached heritage home on tree lined street in downtown Toronto. Wellesley Subway half block away. 1 bedroom w/ensuite, formal dining room, living room, kitchen w/breakfast room, separate TV room, and about a gajillion books to read :) We also have no hidden cleaning fees (don’t you hate those??) and our house keeper takes care of sheets, towels, garbage, cleaning etc when you leave.

Popular amenities for house rentals in The Annex, Old Toronto

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

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$85 SGD$102 SGD$102 SGD$87 SGD$98 SGD$103 SGD$107 SGD$117 SGD$115 SGD$114 SGD$121 SGD$100 SGD
Avg. temp-3°C-3°C2°C8°C14°C20°C23°C22°C18°C11°C5°C0°C

Quick stats about house rentals in The Annex, Old Toronto

  • Total holiday rentals

    Explore 90 holiday rentals in The Annex, Old Toronto

  • Verified guest reviews

    Over 4,680 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    90 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

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