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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.

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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, 138 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
The exterior of the duplex house is shown, featuring a well-maintained front lawn with blooming flowers. The building has a brick façade with large windows framed by vibrant greenery. A small balcony is visible on the upper floor, adorned with potted plants.
Home in Deer Park
4.97 out of 5 average rating, 118 reviews

2-Bedroom House In Deer Park

Welcome to our charming 2-bedroom duplex house nestled in the beautiful Deer Park neighbourhood of Toronto! This cozy Airbnb is the perfect home away from home for your stay in the heart of the city, with subway, shops and parks within 10 minutes' walk. This newly renovated house is on the ground floor of a duplex and boasts an amazing sun-room, beautifully furnished living and dining rooms, a fully equipped modern kitchen and 2 comfortable bedrooms. Parking and laundry is available on request.

Top guest favourite
A well-lit living area features a large window draped with light curtains, allowing natural light to fill the space. A stylish sectional sofa is positioned beside a contemporary coffee table adorned with decorative glass pieces. A TV and chest of drawers complete the inviting setting.
Home in Alexandra Park
4.99 out of 5 average rating, 130 reviews

Stylish Home in Downtown Toronto, Walkable area

Discover Toronto from our newly renovated, spacious apartment with a private balcony on Queen Street W! Steps to trendy spots (bars, restaurants, attractions, groceries, LCBO) and easy streetcar access for city exploration. Enjoy morning Nespresso™ coffee with CN Tower views on the balcony. Key Locations: 2 mins walk to Queen St W and Portland St 8 mins walk to King St W and Portland St 13 mins walk to Trinity Bellwoods Park 13 mins walk to Art Gallery of Ontario 10 mins drive to CN Tower

Guest favourite
A modern living area features a sleek white sofa adorned with yellow and gray pillows. A round black coffee table is positioned in front, displaying magazines. A vibrant artwork hangs on the wall, complemented by a floor lamp and a decorative lantern in the background.
Home in Oakwood Village
4.88 out of 5 average rating, 100 reviews

Spacious 1 BD basement apartment

Forget your worries in this spacious and serene space. Peaceful neighborhood in central Toronto. This unit is everything you need. Perfect for couples. 700 sq ft, brand new furniture, transit-friendly and a 10 minute walk to a variety of restaurants and coffee shops. Transit will take you in Downtown in 20 min. Fresh linens, towels, Wi-Fi, coffee maker, toaster are provided. Guests have a private seperate entrance. I want people to feel comfortable in the space 6ft max height is recomended.

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, 177 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, 590 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
4.86 out of 5 average rating, 104 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
A modern living room features a gray sofa with decorative cushions, a coffee table, and a cozy rug. Shelves against the wall display books and decorative items, with a warm wooden accent above.  A plant and stylish lighting enhance the inviting atmosphere.
Home in University
4.93 out of 5 average rating, 123 reviews

The Robert House: Masterpiece in Harbord Village

The Robert House is a beautiful stylish home in the heart of the city. Located just south of the Annex neighbourhood, east of Toronto’s Little Italy and a stone’s throw from Kensington Market and Chinatown. Enjoy this remarkable home - steps to subway, landmarks, parks, markets, cafes, restaurants, bars & shops. You will remember your stay in this bright & spacious 3+1 bed, 2.5 bath with soaring 10 foot ceilings and high-end finishings.

Guest favourite
Home in Garden District
4.97 out of 5 average rating, 103 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
Home in Corktown
4.99 out of 5 average rating, 240 reviews

Stylish 1870s Home near Distillery District & Old Toronto

Named a Top 10 Toronto stay by BlogTO, this beautifully restored 1870s rowhouse blends historic charm with modern refinement. Thoughtfully designed throughout, it’s steps from St. Lawrence Market, the Distillery District, 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

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, 103 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, 138 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

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Quick stats about house rentals in The Annex, Old Toronto

  • Total holiday rentals

    Explore 100 holiday rentals in The Annex, Old Toronto

  • Verified guest reviews

    Over 4,670 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    100 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

  • 4.8 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

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