House vacation rentals in The Annex, Old Toronto

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Top-rated house rentals in The Annex, Old Toronto

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Guest favorite

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

4.85 out of 5 average rating, 131 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

Guest favorite

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, 106 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 favorite

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, 129 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!

Guest favorite

Home in Downtown Toronto

4.9 out of 5 average rating, 101 reviews

1300sf unique artists loft. Downtown coach house

Stellar 1,300sf artists loft (sleeps 5)! 1920’s coach house on a leafy street In the heart of downtown. Market/Chinatown/AGO/UofT/OCAD/UHN within blocks. Renovated with antique carpets/curios/plush furniture for vibrantly authentic decor. My urban jewel stands apart from cookie cutter condos. The historic exterior is adorned (legally) by the city's finest graffiti artists. You might just want to hang out:-). One parking spot included. Experience Toronto at its comfortable bohemian best!

Top guest favorite

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, 191 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

Top guest favorite

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

4.92 out of 5 average rating, 177 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 favorite

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, 580 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.

Top guest favorite

Home in Corktown

4.99 out of 5 average rating, 230 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.”

Guest favorite

The living space features a modern sofa accompanied by a vibrant area rug. A small dining table with four chairs is positioned near large windows that allow natural light. Wall art and a stylish light fixture enhance the contemporary design.

Home in Trinity-Bellwoods

4.92 out of 5 average rating, 358 reviews

Garden Home @ Trinity Bellwoods Park

City of Toronto Lic. # STR-2009-HSDPBL Come stay in the Trinity Bellwoods area. Enjoy our tree covered deck for coffee/cocktails and a BBQ. Inside, our modern 2 bed renovation with a studio-style layout lets you feel at home. All mod cons. Cable/Netflix. Check In 3pm/Out 11AM. Parking: can be organized for city streets. NOTE: The stairs are narrow to the lower level, where the bathroom, laundry & 2nd bedroom are located. The bedroom has a 6 ft-2in ceiling height only.

Guest favorite

Home in Mississauga

4.89 out of 5 average rating, 114 reviews

Mississauga Bsmt Apartment off of Bloor St!

Basement apartment with seperate entrance and complete privacy, located in Mississauga bordering Toronto. A minute walk to Bloor Street which goes directly to downtown Toronto. For people taking public transportation there is a great connection on Bloor St to the Kipling Subway station and to Square One Mall. If looking to visit downtown Toronto by public transportation, it will take about 50 minutes. Parks and lots of attractions near by. New Baby and Toddler in house.

Guest favorite

A modern staircase with floating wooden steps and glass railings guides the view upward. A framed map of Canada hangs on the wall, complementing the elegant decor. Natural light fills the hallway, enhancing the spacious and bright atmosphere.

Home in University

4.93 out of 5 average rating, 112 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 favorite

A spacious open-concept living area is presented, featuring a cozy couch and two armchairs arranged around a round coffee table. A large TV is mounted on the wall, and a rug with black and white stripes adds a touch of style. Plants and decorative art complete the inviting ambiance.

Home in Old East York

4.97 out of 5 average rating, 196 reviews

Modern and bright private suite.

Enjoy a newly built, professionally designed, roomy 1-bedroom basement apartment in East York Toronto. Conveniently located near the Danforth, Woodbine Beach, parks, and trails, the apartment is a short bus/subway ride or a 15 min drive from Downtown Toronto. Self-contained and spacious, it offers a fully equipped kitchen, new laundry facilities, a queen-sized bed, ample storage, and plenty of natural light.