
House holiday rentals in The Annex, Old Toronto
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Top-rated house rentals in The Annex, Old Toronto
Guests agree: these houses are highly rated for location, cleanliness and more.

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.

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!

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

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).

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.

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.

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

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.”

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

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.

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.
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.
Popular amenities for house rentals in The Annex, Old Toronto
House rentals with a pool

Award Winning Luxury Home with Heated Pool + Sauna

Luxe Haven Heated Pool Sauna Gym

Ravine Paradise ! heated pool and hot tub!

Luxe, Family-Friendly Oasis Home With Outdoor Pool

Guest suite 10 min to subwy w kitchen FREE parking

private backyard SPA oasis in Toronto

Modern Designer Home w/ Pool Open Game Rm/Fire Pit

Victorian Charm – TIFF/FIFA Base in King West
Weekly house rentals

Toronto Oasis: Home Near Ossington Strip

Cozy One Bedroom Retreat

Chic 3BR w/ Parking, King Bed, Full Kitchen, Wifi

Central Toronto

Bright Modern Private Oasis Whole Laneway 3BR 3BA

Luxury Haven in Little Tibet

Toronto Oasis | Cafés, Local Vibes, Subway, Shops

Chic Urban Artist’s Garden Home
Private house rentals

Townhome with Private Rooftop Terrace

Newly Renovated House Sunnybrook Toronto 3parkings

Bright & Cheerful Laneway Home

Peaceful Victorian in Queen West - Super Host

Girls Night Out

Private Midtown Suite 5 min walk to Subway Station

Trinity Quiet Patio 12ft ceiling

Unique Stylish Studio in Great Location!
Quick stats about house rentals in The Annex, Old Toronto
Total rentals
90 properties
Total number of reviews
4.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wifi availability
80 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Destinations to explore
- Flat rentals The Annex
- Rentals with a fireplace The Annex
- Rentals with outdoor seating The Annex
- Pet-friendly rentals The Annex
- Fitness-friendly rentals The Annex
- Family-friendly rentals The Annex
- Rentals with a patio The Annex
- Rentals with a washing machine and dryer The Annex
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Budweiser Stage
- Exhibition Place
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- Clifton Hill
- The Danforth Music Hall
- Toronto Zoo
- Harbourfront Centre
- Financial District
- CF Toronto Eaton Centre
- Niagara Falls State Park
- BMO Field
- Trinity Bellwoods Park
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Legends on the Niagara Golf Course
- Rouge National Urban Park
- Casino Niagara