Vacation rentals in Rosedale, Old Toronto

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Top-rated vacation rentals in Rosedale, Old Toronto

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Top guest favorite

A kitchenette area features a modern sink with a sleek faucet and a minimalist design. A distinctive backsplash displays beige and white tiles, shaped like a crown with five decorative stars. Small appliances, including a kettle and toaster oven, are neatly arranged on the countertop.

Guest suite in Playter Estates

5 out of 5 average rating, 14 reviews

Bright 'Royal Guest Suite'-1926 Home

Bright, clean basement studio apartment with 6'10" ceilings has a separate entrance and is located in the sweet spot of Toronto. 1/2 a block from Chester & Danforth subway in Greektown. You will have all the best access to make Toronto your playground. The elegant unit is naturally cool with fireplace, smart tv, Queen bed with a new firm mattress, memory foam top & multiple pillow types to assure comfort. With a private bathroom heated floor, shower & adorable kitchenette. Sorry, no parking.

Superhost

A cozy living area is presented with a light-colored sofa facing a wooden coffee table. A textured rug covers the floor, adding warmth to the space. In the background, a modern kitchenette is visible, equipped with appliances and shelving for convenient storage.

Guest suite in Rosedale

4.85 out of 5 average rating, 26 reviews

Private Suite in Downtown Home

A perfect balance of quiet convenience with a private suit in the basement of a newly built unit in the residential Toronto neighbourhood of Rosedale only steps away from the subway and a quick walk from the downtown core. - High-speed Wifi & work station in room, perfect for remote work. - Modern living space and fridge, sink and coffee/tea. - Queen sized bed to sleep 2 comfortably. - The summer allows for shared backyard. - 6min walk to Castle Frank subway station, 19min walk to Bloor Yonge

Guest favorite

A spacious dining area is highlighted by a long table draped with a neutral-toned tablecloth. Clear ghost chairs surround the table, creating an airy feel. Above, a distinctive light fixture with multiple bulbs adds character to the softly painted walls.

Apartment in Downtown Toronto

4.94 out of 5 average rating, 35 reviews

Urban Watch Suite in DT Toronto w/ King Bed

✦✦✦✦✦❤✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦ ✦✦✦✦✦✦✦✦✦✦✦✦ ✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦❤✦✦✦✦✦ This unit is AVAILABLE for bookings for the Christmas with discounts. Please contact me directly for the booking instructions. ✦✦✦✦✦❤✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦ ✦✦✦✦✦✦✦✦✦✦✦✦ ✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦✦❤✦✦✦✦✦ Hello travelers, immerse yourself in the vibrant pulse of urban living as you savor the dynamic cityscape from the comfort of our Urban Watch Suite, where every glance captures the essence of bustling streets and the heartbeat of city life.

A cozy living room features a sectional sofa arranged around a striped ottoman. A comfortable armchair is positioned nearby, and a bookshelf filled with a variety of books is seen against the wall. Natural light enters through large windows, enhancing the inviting space.

Home in Rosedale

4.83 out of 5 average rating, 24 reviews

Four Bedroom Rosedale Home

Spread out at this peaceful and centrally located place., in the most prestigious downtown neighbourhood, wooded and tranquil Rosedale. With three work stations, 4 TVs including a 65 inch screen television with over 22,000 live TV channels. The main work station has a computer monitor at a sit-stand desk that turns your modern laptop into an internet connected workhorse. A fully stocked pantry and neighbourhood food shops make cooking in a breeze. Local fine restaurants are a brief stroll away.

Guest favorite

A spacious living room is filled with natural light from large windows, offering city views. A large sectional sofa with soft cushions is placed around a glass coffee table. Occasional chairs with a distinctive pattern complement the elegant decor, highlighted by a decorative chandelier above.

Apartment in St. James Town

5 out of 5 average rating, 12 reviews

Penthouse * Rare * Stunning Views * 2500 sq ft

Be greeted to spacious luxury in the heart of downtown. You'll be surrounded by a tasteful blend of traditional and high end decor - with some pieces dating to early 1900's Europe. Unwind after a long day in the deep soaker tub in front of the fire, while gazing at the city scape just outside the window. Feel at home especially if you desire a chef's kitchen, large and open entertaining spaces with 2 fireplaces, 2 bedrooms, 2.5 bathrooms & private home office. 1 underground parking space incl.

Superhost

The modern kitchen features sleek cabinetry and stainless-steel appliances, including a microwave and oven. A spacious island provides seating and workspace. The living area includes a sectional sofa and a coffee table, with large windows allowing natural light to fill the space.

Hotel room in Church-Wellesley

4.8 out of 5 average rating, 96 reviews

Town Inn Suites

Discover your urban retreat in this spacious 500-square-foot room in downtown Toronto, just a short walk from Yorkville. This suite features a king size bed, fully equipped kitchen, ideal for meals, along with a separate living area filled with natural light and a cozy dining space. Enjoy the privacy of a separate bedroom and a well-appointed bathroom. This is the perfect place for extended stays, just a 5-minute walk to the Yonge-Bloor subway station—ideal for exploring the city!

Top guest favorite

A bright living area features a light-colored sofa and a round dining table surrounded by two chairs. A decorative area rug adds texture to the tiled floor. A television is placed on a low stand, while a door leads to an outdoor space.

Apartment in Playter Estates

5 out of 5 average rating, 40 reviews

Steps to Greektown/Danforth

Cozy, quiet apartment just steps from Toronto’s vibrant Danforth/Greektown neighbourhood. Short 2-minute walk to Pape subway, hundreds of restaurants, cafes and shops. Nearby access to greenspace, bike/running paths in the Don Valley and just a short trip down to downtown or Woodbine Beach. Modern, quiet and clean space with high 8+ ft. ceilings, well-appointed with 100% cotton linens, fully equipped kitchen and TV. 1.5 gigabit fiber internet, private entrance laundry included.

Top guest favorite

A modern living area is highlighted by a sleek sofa and a glass coffee table atop a zebra-patterned rug. An open layout reveals a kitchen area equipped with contemporary appliances. Art pieces adorn the walls, and a smart TV is mounted for entertainment.

Apartment in Yorkville

5 out of 5 average rating, 52 reviews

The One in Yorkville-Previously Four Seasons Hotel

Our chic apartment in the heart of Yorkville is within a five-minutes-walk to ROM and Gardener museums, University of Toronto, libraries, theatre, bookstore, parks, subway stations, church, Whole Foods, and all retail stores, from Chanel, Dior, Holt Renfrew, to COS, Sephora, and Winners. Nestled among Park Hyatt and Hazelton Hotel, our building was previously the historic Four Seasons Hotel, and the upscale area around it is bustling with cafes, restaurants and art galleries.

Guest favorite

The exterior of a historic Victorian home features a warm red brick façade with large windows. A welcoming front porch is framed by neatly maintained gardens, with colorful flower beds enhancing the entrance. The symmetry of the building is complemented by traditional architectural details.

Townhouse in Summerhill

4.96 out of 5 average rating, 46 reviews

Stunning Upscale Toronto - Historic Home/ Hot Tub

Stunning Victorian home w/ huge windows (very bright) & 10 foot ceilings. 1300 SQ feet + basement. Located in prime upscale Summerhill district. Toronto skyline views. Walking distance to Toronto's finest: - 10 mins to Bloor Street (Toronto's 5th avenue) which boasts many designer boutiques, restaurants and galleries' - 2 mins to Summerhill subway station - 2 mins to wine bars, coffee shops and a variety of upscale restaurants - 2 mins to parks - 5 mins to ravine walks

Guest favorite

A modern living area is featured, showcasing a grey couch with light-colored throw pillows. A small coffee table is positioned in front of the couch on a patterned area rug. Lush green plants are visible, adding a touch of nature, while a window allows natural light to enter the space.

Guest suite in Davisville Village

5 out of 5 average rating, 23 reviews

Modern Midtown Manor

Feel taken away from the city in this modern basement apartment. The 2-bedroom unit is equipped with a fully stocked kitchen, living room, dining area, office space, and laundry facilities. It is located in a quiet area of Midtown Toronto and gives you access to all amenities including restaurants, shops and grocery stores. Please note there is no air conditioning, but the apartment is relatively cool and large fans are provided just in case.

Top guest favorite

A stylish living area features a gray sectional sofa paired with decorative pillows. A circular side table holds a small plant and a tray. The wall is adorned with a flat-screen TV, and light-colored wood flooring complements the soft gray walls, enhancing the modern decor.

Condo in The Pocket

4.98 out of 5 average rating, 49 reviews

Unique townhouse studio

Welcome to your urban oasis in the heart of Toronto! Nestled between the vibrant "GreekTown" and the charming "Lesliville" neighborhoods, my cozy multilevel townhouse studio awaits your arrival. With a plethora of restaurants, cafes, and green spaces just steps away, you'll be perfectly situated to explore all that this dynamic city has to offer.

Top guest favorite

A cozy living area features a spacious grey sectional sofa and a wooden coffee table. Natural light floods in through a large window dressed with soft, patterned curtains. Two potted plants add a touch of greenery, enhancing the inviting atmosphere.

Condo in St. James Town

5 out of 5 average rating, 30 reviews

Chic & Modern Escape Near Yorkville

Welcome to our home at James Cooper Mansion condos! A cozy unit in a modern building that's nearby incredible Bloor shopping and trendy Yorkville restaurants. ✓ 1st floor unit = no elevator wait! ✓ Spacious 1100 sq ft ✓ Safe indoor parking ✓ Two sets of keys ✓ 24/7 security desk ✓ Subway station (1 min walk)