Apartment holiday rentals in The Annex, Old Toronto

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Top-rated apartment rentals in The Annex, Old Toronto

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Guest favourite
A panoramic view of downtown Toronto reveals a vibrant skyline and lush green parks. The image captures urban development along the waterfront and railway, framed by clear blue skies and scattered clouds, showcasing a blend of nature and cityscape.
Flat in Entertainment District
4.89 out of 5 average rating, 53 reviews

49th Floor Penthouse with Downtown Toronto Views

Welcome to my cherished home in the heart of downtown Toronto! I'm thrilled to invite you to experience the vibrant atmosphere of the city, with easy access to the Entertainment District - the CN Tower, Rogers Center, Waterfront, and many more! My prime location ensures you can explore the best of Toronto, experiencing local gems and trendy neighbourhoods. Marvel at breathtaking cityscapes through floor-to-ceiling windows and a top-floor balcony in this luxury condo. Your urban escape awaits!

Guest favourite
A warm and inviting living area features exposed brick walls and a large wooden dining table surrounded by black chairs. Soft lighting from a vintage chandelier casts a gentle glow over a cozy sofa and a stylish entertainment unit, creating a sense of comfort.
Flat in Annex
4.94 out of 5 average rating, 118 reviews

Luxurious Annex/Yorkville 1300 Sq Ft & Parking

Beautifully appointed, top quality furnishings & amenities , spacious Yorkville/Annex rental. Full 1300 sq foot. apartment located within a Heritage Victorian Brownstone! Exceptionally located, walking distance to subway, restaurants and all the sights! Walk to Casa Loma, Royal Ontario Museum & Yorkville. Parking, Wifi, Chromcast, Fibe TV, Local High Def TV included. Fully equipped gourmet kitchen. Air Conditioned. Digital safe for valuables. Treat yourself to pantry snacks, coffee & tea.

Top guest favourite
A modern living area features a dark sofa and a light blue chair, positioned around a glass-top coffee table. A large wall-mounted TV is displayed, while decorative lanterns adorn a white console table with wicker baskets. Natural light streams through a window beside a potted plant.
Flat in Little Portugal
4.9 out of 5 average rating, 128 reviews

Cozy Private Apt DT Toronto + Free Parking

Step into this bright, cozy 1BR 1BA private suite in Toronto’s West End—minutes to great cafés, restaurants, shops, and easy transit to downtown. Ideal for couples, friends, or business travelers who want comfort and convenience. ✔ Queen Bedroom + Sofa Bed (Sleeps 4) ✔ Full Kitchen + Dining ✔ Workspace ✔ Smart TV + Streaming ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Shared Backyard ✔ Self Check-In Enjoy Toronto like a local! Coming for the 2026 World Cup? BMO Field is ~7 mins by car/taxi!

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.
Flat in Annex
4.87 out of 5 average rating, 100 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.

Top guest favourite
A sunset over the water is portrayed, with a golden sun reflecting on the calm surface. The horizon features a silhouette of trees, creating a serene atmosphere. Soft waves ripple gently in the foreground, enhancing the tranquil setting.
Flat in Centre Island
4.95 out of 5 average rating, 110 reviews

Toronto Island Wonderland View

Toronto Islands are a 10 minute ferry ride away from downtown Toronto. Switch from the hustle and bustle of the city to the tranquillity of one of Toronto's most coveted parks. Unique to any other metropolitan city, Toronto Island has limited vehicle access. This car free area boasts 6 kilometres of nature walks, children and pet friendly access to beaches, Centre island amusement park, artist exhibitions, restaurants and even a nude beach. A perfect getway for the hybrid vacationer.

Top guest favourite
A charming brick facade is displayed, featuring a welcoming entrance with steps leading up to a door flanked by large windows. Lush greenery surrounds the exterior, providing a sense of privacy. A stone walkway leads to the front door, enhancing the inviting appearance.
Flat in Toronto
4.9 out of 5 average rating, 39 reviews

High Park Gem- Guest Suite

Your family will be close to everything when you stay at this centrally located place. 5 Minutes from TTC Dundas West , and UP Express Bloor Station. This gem is located close to High Park and the neighbourhood of Roncesvalles. You wont miss a beat! Surrounded by lush trees and greenery -this guest house is steps away from public transit - easily from Union Station or Pearson Airport. Enjoy all the wonderful things Toronto has to offer while staying at the guest house.

Guest favourite
Flat in Mirvish Village
5 out of 5 average rating, 12 reviews

Trendy 2-Story Loft in the Annex! Steps to Train!

Experience the epitome of urban living in this trendy 2-story loft apartment, perfectly situated in the Annex neighborhood of Toronto! This stylish apartment offers a modern and comfortable retreat with 4 bedrooms, 3.5 bathrooms, and a host of amenities including a fully equipped kitchen, Smart TV, and Wi-Fi. With steps to the train, you'll have easy access to all the city has to offer. Enjoy the convenience of being close to downtown, while also having a relaxing space to unwind.

Superhost
An open-concept kitchen and living area is shown, featuring modern white cabinetry, stainless steel appliances, and a central island with a wooden countertop. A cozy gray sofa is positioned nearby, accompanied by a bright yellow throw. Stairs lead to an upper level, enhancing the spacious feel.
Flat in Casa Loma
4.74 out of 5 average rating, 108 reviews

Bright Apartment in Casa Loma

Newly renovated suite with a private entrance and free parking in the heart of beautiful Casa Loma. Enjoy this spacious open-concept apartment with a dedicated workspace and plenty of room for guests to feel at home. 7-minute walk to Dupont Subway Station and 4 minutes to the historic Casa Loma Estate. Enjoy this charming area with some of Toronto's best restaurants and the Taragon Theatre. The host is dedicated to make our experience as enjoyable as possible!

Top guest favourite
A bright living room is filled with natural light, featuring a cozy couch and two large cushions arranged on the floor. A round coffee table sits at the center, adorned with decorative objects. Green plants add a touch of nature, complemented by light, airy curtains.
Flat in Annex
4.98 out of 5 average rating, 53 reviews

Sundrenched 1BR Downtwn Apt-Views & Free O/N Prkng

THE ANNEX OASIS Unwind on a lush, rainforest-inspired balcony with sweeping downtown views - steps from cafes, trendy shops & restaurants, culture & UofT. Our spacious 1-BD home in Annex blends comfort, charm & location. ➜ 3-min walk to St. George Subway & UoFT ➜ Free overnight street parking ➜ Complimentary breakfast snacks, coffee & tea ➜ 2 workstations+high-speed WiFi ➜ 60" Home Theater Smart TV ➜ Beautiful sunsets from balcony Your homestay in Toronto.

Guest favourite
A modern living area features a black sofa, round ottoman, and a small coffee table positioned on a textured rug. A bright artwork piece is mounted on the white wall, with the kitchen area visible in the background, showcasing essential appliances and a minimalist design.
Flat in Roncesvalles
4.94 out of 5 average rating, 108 reviews

Bright & Modern Lower Level On Lansdowne

Located on Lansdowne between Queen and Dundas West, this newly renovated one bedroom lower level unit with separate entrance is a bright and open floorplan you will easily enjoy during your stay. It’s proximity to downtown and highway access while being close to all the best Toronto West neighbourhoods makes this location truly special. Come stay in this convenient, private, and modern unit with all the comforts of home.

Top guest favourite
A welcoming living area is presented with large bay windows allowing natural light. Comfortable seating is arranged around a circular coffee table, complemented by decorative elements like artwork on the walls and a potted plant in the corner.
Flat in Palmerston
4.97 out of 5 average rating, 37 reviews

Beauty 1800 sq ft, 2 storey, 2 beds, Little Italy

Beautiful, 1800 square feet, two level apartment. Laundry, 2 washrooms, two bedrooms with really comfy matresses, full kitchen. Deck for outdoor lounging or dining. Close to many restaurants, bars, transport or a great spot to just start wandering downtown Toronto. Street parking available through the City. Go to City of Toronto temporary parking permit website. Easy and inexpensive. PRINT PERMIT BEFORE YOU ARRIVE.

Top guest favourite
A dining area is presented with a wooden table set for meals. A textured vase holds an arrangement of greenery and foliage. Black-framed photographs adorn the wall, creating an artistic backdrop, while a pendant light offers soft illumination.
Flat in Wychwood
4.97 out of 5 average rating, 98 reviews

Renovated Modern 2 Bedroom Suite w/ City Views

Experience the city like a local in this newly renovated two-bedroom suite. This ample, bright, airy space has beautiful city line views. We are centrally located (steps away from Casa Loma and downtown) with plenty of options for food, drinks, and local shops. The area has excellent walkability and great transit access. 24km from/to Pearson Airport and 6km from/to Billy Bishop Airport

Popular amenities for The Annex, Old Toronto apartment rentals

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Quick stats about flat rentals in The Annex, Old Toronto

  • Total holiday rentals

    Explore 150 holiday rentals in The Annex, Old Toronto

  • Nightly prices starting at

    The Annex, Old Toronto holiday rentals start at £15 per night before taxes and fees

  • Verified guest reviews

    Over 3,650 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    150 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

  • 4.7 Average rating

    The Annex, Old Toronto stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    The Annex, Old Toronto’s top spots include Royal Ontario Museum, Bata Shoe Museum and Spadina Station

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