Holiday houses in Rosedale

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Top-rated holiday rentals in Rosedale

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

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Top Guest favourite
A modern suite features a spacious bed with a tufted headboard, complemented by light-colored bedding. A glass partition delineates the living area, which includes a round dining table and comfortable seating beneath large windows. A sleek workspace with a printer is also present.
Condo in Yorkville
4.9 out of 5 average rating, 313 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.

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 Rosedale
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, 219 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.

Guest favourite
Home in Summerhill
5 out of 5 average rating, 22 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
5 out of 5 average rating, 112 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!!!

Top Guest favourite
The exterior of a detached heritage home is showcased, featuring a brick façade and large windows. The entrance is framed by vibrant orange flowers and lush greenery. A yellow awning extends over the front door, adding a cheerful touch to the welcoming ambiance.
Home in Church-Wellesley
4.92 out of 5 average rating, 146 reviews

Entire Heritage House for Two! 1BR 3BA 2 Liv Rms

Beautiful detached heritage home on a quiet, tree-lined street in the heart of downtown Toronto. Wellesley Subway Station is just half a block. We offer one spacious bedroom with ensuite bathroom, formal dining room, living room, modern kitchen with bright breakfast area, and tv room. You’ll also find an extensive library throughout the home — perfect for curling up with a book during your stay. Our pricing is transparent, with a modest cleaning fee and no surprises at checkout :)

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 Cabbagetown
4.93 out of 5 average rating, 184 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.

Superhost
Apartment in Toronto
5 out of 5 average rating, 9 reviews

Charming Apartment with Patio in Midtown Toronto

Beautifully renovated 1-bedroom in a quiet, secure building at Oriole Parkway. Features a brand-new kitchen, modern bathroom, fresh paint, and a spacious private patio perfect for relaxing or entertaining. Steps from Yonge & Eglinton, Eglinton Park, cafés, shops, and transit. Enjoy peaceful living with city convenience - ideal for professionals or couples seeking comfort, style, and location in one of Toronto’s best neighbourhoods. 1 parking spot is available at the property.

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 Summerhill
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 Upper Jarvis
4.99 out of 5 average rating, 110 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
An impressive view of a modern high-rise building is captured from below, showcasing the architectural details of the glass façade and concrete structure. A bronze statue stands prominently at the base, adding a cultural element to the urban landscape.
Condo in Yorkville
4.9 out of 5 average rating, 182 reviews

Yorkville Toronto Breakfast Included

Entire apartment is yours to enjoy. I am the owner: I always clean-this is not multi operated. Laundry is carefully cleaned. New leather reclining sofa. I include breakfast groceries at no charge. Coffee, tea, milk, 2 apples, 2 oranges, 2 bananas, 4 bagels, cream cheese, strawberry jam, dozen eggs, butter, onion, tomatoes. Walk to Whole Foods, Starbucks. University.50" TV + 32 " TV, includes NETFLIX, AMAZON PRIME VIDEO, INTERNET.

Guest favourite
Condo in Toronto
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 holiday rentals

When is the best time to visit Rosedale?

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Quick stats about holiday rentals in Rosedale

  • Total holiday rentals

    Explore 110 holiday rentals in Rosedale

  • Nightly prices starting at

    Rosedale holiday rentals start at $42 AUD 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 holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Rosedale rentals

  • 4.8 Average rating

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

  • Nearby attractions

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

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