Holiday houses in Rosedale, Old Toronto

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Top-rated holiday rentals in Rosedale, Old Toronto

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Condo in Yorkville
4.9 out of 5 average rating, 314 reviews

Luxury Yorkville Escape | Condo in Prime Location

Discover refined living in this beautifully furnished apartment in Yorkville Toronto’s most glamorous & exclusive neighborhood. With new furniture & modern appliances, this space blends comfort with sophistication. Step outside and find yourself surrounded by luxury boutiques, acclaimed restaurants, chic cafes, & world-class art galleries. With Bay subway station just a 3 minute walk away, the entire city is at your fingertips. Elevate your lifestyle in a place where elegance meets convenience.

Superhost
Condo in Yorkville
5 out of 5 average rating, 14 reviews

Stunning Condo Beautiful Views Heart of Yorkville

Indulge in luxury at our stunning 2-bedroom, 2-washroom Downtown Toronto Yorkville retreat! Unwind in style on your private balcony overlooking the city, or relax in the heart of Toronto's upscale neighborhood. Perfect for couples or friends seeking a luxurious getaway. Amenities: - 2 spacious bedrooms - 2 modern washrooms - Private balcony with city views - Upscale decor and amenities - Prime Yorkville location -Gym and Pool Book now and experience the best of Toronto's luxury hospitality!

Guest favourite
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 Midtown
4.89 out of 5 average rating, 38 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.

Top Guest favourite
A modern two-story cottage is surrounded by lush greenery and trees. The exterior features a combination of natural wood and dark green siding. A covered porch is visible with a personal entrance and outdoor seating. Bicycles are parked nearby, enhancing the outdoor activities available.
Guest suite in Toronto
4.95 out of 5 average rating, 220 reviews

Cozy small newly built Toronto Islands getaway

Escape to a modern cottage on Toronto Island Looking onto Lake Ontario is our newly constructed modern home. Enjoy our cozy private guest suite in our family home with a kitchenette, ensuite bathroom, and private entrance Just a quick ferry ride from the bustling downtown core come explore the Toronto Islands which is the biggest car-free community in North America; with beaches, trails & skyline views as well as an amusement park in the summer. We also have 2 bikes you can use to explore.

Top Guest favourite
Home in Downtown Toronto
4.99 out of 5 average rating, 249 reviews

Stylish 1870s Home near Distillery District & Old Toronto

Visiting for fifa? Stop here...Steps from the Distillery District downtown, this Top rated listing is a beautifully restored 1870s row-house (townhouse) that blends historic charm with modern refinement. Thoughtfully designed throughout, it’s located downtown also close to St. Lawrence Market, and some of the city’s best cafés and restaurants. In the evening, unwind in the serene, charcoal-toned bedroom beneath the warm glow of a statement chandelier—your refined Toronto retreat awaits

Guest favourite
Home in Midtown
5 out of 5 average rating, 23 reviews

Summerhill 2BR Home • Designer Style • Sleeps 4

Design-forward retreat with a sunlit living room—large leather sofa, lounge chairs, wall-mounted TV, and a sleek linear fireplace. Glass-top dining for four flows to a chef-ready galley kitchen with wall oven, quartz counters, and a breakfast bar for two; slide the doors to a private, greenery-framed deck. Two serene bedrooms (king + queen). Spa bath with walk-in shower, and soaking tub. In-home laundry, hardwood floors and fast Wi-Fi. Modern and thoughtful decor—perfect base for your stay.

Top Guest favourite
A spacious living area features a dark gray sectional sofa and a wooden coffee table adorned with decorative items. Natural light illuminates the space, highlighting a gas fireplace underneath the wall-mounted television. A dining area with four chairs is visible in the background.
Home in Toronto
4.99 out of 5 average rating, 116 reviews

New! Private 1BR in Toronto by Danforth, Sleeps 4

Welcome to our stunning, newly renovated home in Toronto’s Old East York neighborhood, just a two minute walk from trendy Danforth Avenue and Pape Subway Station. This bright and airy, coastal-inspired retreat blends the comfort of home with the soothing simplicity of Maritime charm. This private oasis spans 750 square feet and is ideal for those seeking a peaceful escape in East York, with easy access to the best of Toronto. We'd put our accommodations up against the hotels of Toronto!!!

Guest favourite
Home in Yorkville
4.89 out of 5 average rating, 9 reviews

Stylish Victorian home with free parking

A beautifully-appointed century home in the Yorkville/Rosedale neighbourhood of downtown Toronto. Centrally located within walking distance to many attractions such as the Royal Ontario Museum, the Yorkville shopping area, and Bloor Street. Located adjacent to Rosedale subway station or a few minutes walk from Bloor/Yonge station. Across the street, there is a beautiful public park called Ramsden Park with tennis courts, beautiful trails and lovely surroundings, including picnic tables.

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.
Apartment in Downtown Toronto
4.94 out of 5 average rating, 187 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
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 Midtown
4.94 out of 5 average rating, 63 reviews

Stunning Historic Upscale Toronto Home

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

Top Guest favourite
A bright kitchen area features a central island with seating for three. Modern cabinetry and appliances are visible, including a microwave and coffee maker. Warm wooden floors and recessed lighting enhance the inviting space.
Apartment in Downtown Toronto
4.99 out of 5 average rating, 111 reviews

King bed, Big kitchen, Free Parking, Central

Welcome to 9 Selby Street – Downstairs Apartment. We hope you enjoy your stay in our home and city. Our neighbourhood is close to popular attractions, offers great walks, and has convenient stores across the street. The subway and transit are a one-minute walk away. -Private apartment with own laundry -Spacious and bright kitchen -Smart tv, working desk, fast Wi-Fi -Cozy living room with a huge TV -Sleeping: Bedroom has luxury King bed, living room has 2 futons (full size)

Guest favourite
Condo in Yorkville
5 out of 5 average rating, 12 reviews

Yorkville Skycrest Penthouse | King Bed | Gym

This is one of a kind Penthouse style unit with the best views in the city in the highest end area of Toronto - Yorkville - 2 Bedrooms with King Beds and remote control blinds. - Sofa Bed in the living area - Sleeps up to 6 guests - Bathroom with bathtub and heated floors - Fully stocked kitchen with modern appliances - Nespresso Coffee Machine - In-suite Washer & Dryer - 55" Smart TV - High-speed Wi-Fi

Popular amenities for Rosedale, Old Toronto holiday rentals

When is the best time to visit Rosedale, Old Toronto?

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Avg. price$194 NZD$214 NZD$182 NZD$239 NZD$242 NZD$244 NZD$227 NZD$247 NZD$229 NZD$209 NZD$187 NZD$211 NZD
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Quick stats about holiday rentals in Rosedale, Old Toronto

  • Total holiday rentals

    Explore 110 holiday rentals in Rosedale, Old Toronto

  • Nightly prices starting at

    Rosedale, Old Toronto holiday rentals start at $50 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,000 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Rosedale, Old Toronto holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Rosedale, Old Toronto rentals

  • 4.8 Average rating

    Rosedale, Old Toronto stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Rosedale, Old Toronto's top spots, include Evergreen Brick Works, Bloor–Yonge Station, and Bay Station