Holiday rentals in The Annex, Old Toronto

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Top-rated holiday rentals in The Annex, Old Toronto

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Top guest favourite
A bronze sculpture of a historical figure stands prominently at the forefront, with a modern high-rise building visible in the background. The glass and steel facade reflects the urban environment, emphasizing the contemporary architectural design surrounding the area.
Apartment in Yorkville
4.99 out of 5 average rating, 69 reviews

High-Floor 1BR in Yorkville | Walk Everywhere

Housed in a former Four Seasons Hotel in Toronto’s prestigious Bloor-Yorkville neighbourhood, this modern high-floor condo places you in the heart of downtown Toronto — walkable, elegant, and just steps from museums, acclaimed restaurants, luxury retailers, boutique shops, and major subway lines. Inside, the fully renovated 1-bedroom features soaring 9-foot ceilings, designer furnishings, curated artwork, luxury bedding, and sunlit bay windows — a boutique city escape for solo or duo travellers.

Top guest favourite
The living room is furnished with a modern gray sofa adorned with accent pillows. A coffee table, featuring a stack of magazines and decorative items, sits on a textured area rug. A television is mounted above a blue cabinet against a light gray wall, with framed art and a plant nearby.
Guest suite in Trinity-Bellwoods
4.96 out of 5 average rating, 416 reviews

Ossington Rowhouse + Private Garden

Relax with a glass of wine in your own backyard garden at this romantic urban cottage—a 700 sq ft pied-à-terre on two private floors of a designer's 4-level townhouse just off the Ossington strip. This calm oasis is perfect for couples or business trips, with high-speed internet and flexible work spaces. Cook in the fully equipped kitchen, or discover Toronto's best bars and restaurants a few steps from home. Explore the city easily on foot, plus close transit with a stop right at your doorstep.

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.

Guest favourite
A modern multi-story condominium building features large glass balconies and expansive windows, reflecting the clear blue sky. Surrounding trees provide greenery and contrast with the sleek architecture, creating a vibrant urban atmosphere.
Flat in Fort York
4.95 out of 5 average rating, 39 reviews

Little Fort

Welcome to the Lil Fort! This cozy 1-bedroom condo offers an open concept living/dining area, and a secondary entrance via your private patio . Just steps from Fort York Park, the lakefront, and downtown dining/entertainment. Enjoy a comfy queen bed, 65” 4K TV, full kitchen, and relaxing bathroom. Skip the elevator—stay on the main floor and unwind in style! Keep it simple at this peaceful and centrally located place. Walking distance to entertainment district, shopping. Parks, and more!

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
4.85 out of 5 average rating, 101 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.

Guest favourite
A spacious sleeping area is furnished with a large bed covered in a white quilt, accompanied by neatly arranged towels. A desk with a computer is positioned nearby, while a decorative rug adds texture to the polished concrete floor. Exposed brick walls provide a touch of character.
Flat in Cabbagetown
4.93 out of 5 average rating, 172 reviews

Modern Victorian

Modern stay in a Cabbagetown Victorian. Welcome to our renovated, self-contained basement apartment in the heart of Cabbagetown, Toronto. This chic space is ideal for solo travelers or couples. Our apartment is nestled in the charming Cabbagetown neighborhood, known for its Victorian houses, tree-lined streets, and vibrant atmosphere. Cafes, restaurants, and boutiques are within walking distance, and nearby parks offer tranquil escapes. Book now to experience the best of Toronto.

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, 105 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.

Guest favourite
A modern high-rise condominium building is visible, featuring a sleek façade of glass and metal. The surroundings include various city structures and signage, with a mix of urban architecture and a cloudy sky above.
Apartment in Entertainment District
4.94 out of 5 average rating, 154 reviews

Luxurious heart of downtown condo next to CN Tower

Welcome to the heart of the city! A non-shared 1-bedroom condo with a full-sized kitchen. My condo is located just across the street from the CN Tower admission booth. 5-10 minutes walking distance to the Aquarium, Rogers Center, Air Canada Center, and Union Station. A few blocks from the entertainment district, endless dining, and shopping options. Fashionably furnished and decorated to be your perfect home away from home.

Top guest favourite
A modern high-rise condominium building is captured against a cloudy sky. The sleek facade features large windows and a combination of brick and glass elements. Surrounding urban architecture contributes to the vibrant cityscape.
Apartment in Entertainment District
4.96 out of 5 average rating, 158 reviews

Across Street from CN Tower,Rogers,Aquarium,MTCC!

Welcome to the heart of the city! A non-shared 1-bedroom condo with a full-sized kitchen. My condo is located just across the street from the CN Tower admission booth. 5-10 minutes walking distance to the Aquarium, Rogers Center, Air Canada Center, Union Station. A few blocks from the entertainment district, endless dining, and shopping options. Fashionably furnished and decorated to be your perfect home away from home.

Guest favourite
A bright living area is filled with natural light, showcasing large windows that provide a panoramic view of the city. A comfortable grey sofa and a distinctive red chair are positioned around a low table, with a large TV and decorative elements enhancing the space.
Loft in Downtown Toronto
4.91 out of 5 average rating, 363 reviews

Panoramic Views in Bright Loft + Free Parking

The loft has more windows than it has walls and offers a clear view of the city sky. Located in the heart of downtown Toronto, you're close to all major attractions, trendy restaurants, bars, and coffee shops. Toronto's legendary Fashion District is where you'll find all the action. If you're here for work, you'll be walking distance to most ad agencies, software companies, and a 15 min walk to the financial district.

Guest favourite
A modern kitchen area showcases sleek white cabinetry and a polished countertop with an under-mount sink. A subtle mosaic backsplash complements the stainless-steel appliances. An inviting dining space is highlighted by a colorful area rug and natural light filtering through large doors.
Tiny home in Midtown
4.91 out of 5 average rating, 122 reviews

Zen Oasis Tiny House - Entire house to yourself!

Beautifully-designed Japanese Zen tiny house features a private inner courtyard. This is a bright space with lots of natural light from 13 foot ceilings and floor-to-ceiling windows and radiant heated floors. 8 minute walk to the Bloor subway line. Minutes from trendy Geary Street, Bloordale, Dovercourt Park. Restaurants, cafes, bakeries, variety stores, pharmacy are conveniently located just steps away.

Superhost
The living area features a gray sectional sofa paired with two wooden coffee tables, each adorned with potted plants. A large television stands against the wall opposite the seating. The glass doors lead to a city view, showing the evening skyline.
Flat in Yorkville
4.88 out of 5 average rating, 26 reviews

Cozy 1BR/1Bath @Yonge/Bloor Subway Free parking

Unbeatable location in downtown Toronto. This cozy Condominium definitely will make yourself feel like home! Either for business trip or visiting the kids at University of Toronto, even simply a family holiday, you will find our place perfectly suitable for your needs. Parking also FREE with the unit (subject to prior reservation).

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Quick stats about holiday rentals in The Annex, Old Toronto

  • Total holiday rentals

    Explore 300 holiday rentals in The Annex, Old Toronto

  • Verified guest reviews

    Over 10,120 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wifi availability

    290 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 Royal Conservatory of Music

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