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Holiday houses in The Annex, Old Toronto

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in The Annex, Old Toronto

  • Total holiday rentals

    Explore 270 holiday rentals in The Annex, Old Toronto

  • Nightly prices starting at

    The Annex, Old Toronto holiday rentals start at $29 AUD per night before taxes and fees

  • Verified guest reviews

    Over 10,440 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wi-Fi availability

    270 of The Annex, Old Toronto holiday 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

Top-rated holiday rentals in The Annex, Old Toronto

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

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Top Guest favourite
The kitchen features modern cabinetry and stainless steel appliances, including a coffee maker. An island with seating accommodates guests. A dining area with a table is visible, alongside a cozy living space with a blue couch, a decorative painting, and potted greenery.
Home in Midtown
4.99 out of 5 average rating, 94 reviews

Private 2BR Home Sleeps 6 Near Subway

Welcome to The Laneway Suite! A newly built, 1000 square foot, 2 storey, detached laneway house. Includes private entrances, Smart Lock, full kitchen with island and amenities, 1.5 bathrooms, 2 Queen bedrooms with 32” Smart TV, a living room with a comfy Queen size pull-out couch and 65” Smart TV, a dining room, and a private backyard patio. The house is completely private! Whether you’re travelling with your family, your friends, by yourself or on a business trip, this is your perfect getaway!

Guest favourite
A modern building featuring a glass facade stands prominently along a tree-lined street. The architecture showcases a blend of contemporary and traditional design, with a mix of vehicles parked and moving along the road, indicating a vibrant urban atmosphere.
Apartment in Yorkville
4.75 out of 5 average rating, 73 reviews

Cozy 1+1 Condo in Yorkville + free parking

Formerly a Four Seasons hotel suite, now fully renovated, this 1 bedroom plus 1 office/den condo with free parking is in the most luxurious area of Toronto: Yorkville. Walking distance to U of T, high end restaurants, cafes, bars and shopping stores, Royal Ontario Museum, and the subway. Smart TV, Bell Fibe, Netflix,& Wifi. Large windows with a breathtaking view and tons of natural light. Walk in Closet for Storage, Washer & Dryer Don’t miss out on this elegant and unforgettable stay!

Guest favourite
A modern living area features a dark gray convertible sofa and a small dining table near the windows. Natural light enters through two large windows, framed by light curtains. A well-equipped kitchen is visible in the background, showcasing stainless steel appliances and a white countertop.
Apartment in Midtown
4.86 out of 5 average rating, 117 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.

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, 118 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
Condo in Downtown Toronto
5 out of 5 average rating, 16 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

Top Guest favourite
A comfortable living area features a large sectional sofa adorned with decorative cushions. A rustic coffee table sits at the center, complemented by warm lighting from a stylish lamp. Natural light filters through two large windows, enhancing the room's inviting feel.
Home in Downtown Toronto
4.97 out of 5 average rating, 74 reviews

Bellwoods Flat with Rooftop Patio & CN Tower View!

This trendy, private, fully appointed apartment located just off Dundas West is the perfect place to work or enjoy Toronto's best restaurants, nightlife, and culture while still having a quite place to hangout and host friends! The 2nd floor century home apartment is 700sqr ft with a private 150sqr ft deck, king bed, washer and dryer, gas range, and dishwasher. It's 1 minute from Dundas W, 5 minutes from Queen West, 10 minutes from Kensington Market, and Trinity Bellwoods.

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.
Apartment in Yorkville
5 out of 5 average rating, 84 reviews

The One in Yorkville-Previously Four Seasons Hotel

Our 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 spacious living area features exposed brick walls and high ceilings. A light-colored curved sofa is positioned around a round coffee table, enhancing comfort. Natural light pours in through large windows and a skylight, creating an inviting atmosphere. The area is accented by tasteful artwork.
Loft in Midtown
4.98 out of 5 average rating, 66 reviews

SOHO Warehouse Style Loft in Annex/Bloor St

Welcome to The Annex Loft located right off Bloor St. Experience a rare opportunity to stay in this 1,800 sq ft Brooklyn-style loft, nestled within a historic Victorian house in one of Toronto's premier neighborhoods. Conveniently located near Spadina and Bathurst subway stations, as well as streetcar and bus services, city exploration is a breeze. You’ll also be within a short distance of top Toronto landmarks such as the Royal Ontario Museum and Casa Loma.

Guest favourite
A spacious living room features a white sectional sofa and a contemporary coffee table on polished wooden floors. Natural light enters through large windows, complemented by a decorative brick fireplace and lush green plants. A ceiling fan enhances airflow in the inviting space.
Home in Midtown
4.85 out of 5 average rating, 97 reviews

Charming, Bright Victorian Townhouse in the Annex

3 level, 2-bedroom sun-filled unit situated in the Annex. Brick fireplace (decoration piece), 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 or Spadina Subway, Casa Loma, Yorkville, University of Toronto, and museums. One outdoor parking spot provided .

Superhost
Apartment in Midtown
4.75 out of 5 average rating, 64 reviews

Spacious 1 Bed w/ Patio Walk up by Subway

Stay in one of Toronto's most sought-after neighborhoods. This 1-bedroom suite with a spacious private patio offers the perfect balance of comfort, convenience, and location. Just steps from Bathurst & Bloor Subway Station, you'll be minutes from downtown, U of T, Kensington Market, Yorkville, Queen Street West, and Toronto's top restaurants, cafés, and nightlife.

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 Midtown
4.88 out of 5 average rating, 270 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 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.
Apartment in Midtown
4.98 out of 5 average rating, 99 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

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