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

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

4.96 out of 5 average rating, 109 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.

Guest favorite

Home in Downtown Toronto

4.9 out of 5 average rating, 105 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!

Guest favorite

The living room is enhanced by natural light from the windows, which are adorned with sheer curtains. A gray sofa faces a mounted flat-screen TV, and a sleek white entertainment unit is situated below it. Light hardwood flooring adds warmth to the cozy space.

Home in Dovercourt Village

4.9 out of 5 average rating, 99 reviews

Toronto Modern Haven: 1 BR w/ Queen Sofa Bed

Welcome to your urban oasis in the heart of Toronto located on the main floor! This modern retreat offers a fully equipped kitchen, a cozy living room with a sofa bed, and a bedroom with a queen-size bed. Immerse yourself in the vibrant energy of the city during the day, and relax in this peaceful haven at night. Indulge in local flavors at nearby eateries, discover hidden gems in eclectic neighborhoods, and soak in the city's iconic skyline views. Your perfect Toronto getaway starts here!

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, 193 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 modern home with a striking design features large reflective windows and a mix of black and stone exterior elements. A driveway leads to a garage, with a sleek car parked nearby. The front lawn is well-maintained, bordered by a sidewalk and trees.

Home in Islington

4.99 out of 5 average rating, 150 reviews

Basement Apartment - New Build!

Full basement apartment of a brand new home which was recently featured in Toronto Life Magazine. Fully loaded with brand new appliances, including a dishwasher and laundry. The best sound dampening we could implement - it's very quiet. Incredible home gym and foosball table. Nice outdoor dining and BBQ area. 1 parking space in the driveway included, however, street parking isn't usually an issue, although technically not allowed. Kipling station and Loblaws are close by (pics attached).

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, 583 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

The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.

Home in The Beaches

4.99 out of 5 average rating, 155 reviews

Heated Pool-tub Open 365 Days

Welcome to the Toronto Beach. We are right next to the lake and have a HEATED private pool and spa that are both open year round. Explore local shops on the high street and swim, kayak (provided), volleyball, basketball and tennis courts right beside us. In winter, an outdoor ice rink (skates provided), cross-country ski trails, and lots of walking to be had. We decorate for the holidays, and the house has a real wood burning fireplace. **note quiet hours are 11:00 pm to 7:00AM

Top guest favorite

A modern living area is highlighted by a spacious gray sectional sofa adorned with colorful cushions. An artistic chandelier hangs above a dining table, while large windows offer views of the outdoor space. The staircase features glass railings, enhancing the open design.

Home in Corktown

4.99 out of 5 average rating, 232 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 favorite

An open-concept living area features a light-colored sofa and a chic coffee table, complemented by a neutral rug. A staircase leads to the upper floor, while a dining area is visible in the background near large windows allowing natural light.

Home in Islington

4.94 out of 5 average rating, 109 reviews

Luxury Home - 5 min from airport, 15 to downtown

The stunning house in Etobicoke is only a few minutes from the Airport and City Centre. This spacious open concept, rare luxury modern home, is beautifully designed and decorated. It is a fully stocked home and will have everything you could ever wish for a short-term stay. Perfect for large families and groups! min age 25 yrs to book. Room 1 king bed Room 2 queen Room 3 twin and another twin roll out Room 4 queen no party policy or excessive noise. this is a quiet listing

Guest favorite

A living area features a comfortable brown sofa with red cushions and a rustic coffee table at its center. A flat-screen television sits on a white stand, while potted plants add greenery to the space. Natural light enters through sliding glass doors.

Home in Little Portugal

4.91 out of 5 average rating, 208 reviews

Charming coach house / guest house downtown

Private and secluded, completely separated, fully serviced and renovated guest house / urban cottage with a beautiful private patio nestled among the mature trees of Dufferin Grove - one of Toronto's most vibrant and interesting neighbourhoods. Find quiet, peace and tranquility in a private oasis, tucked away behind trees and the residential streets, located in the middle of Toronto's trendiest urban centres: Little Italy, Dundas West, Ossington, Little Portugal and Queen West.

Guest favorite

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, 181 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 favorite

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, 114 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.