Holiday rentals 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 well-appointed bedroom features a spacious bed adorned with crisp white linens and a soft throw. Artistic wall decor complements the natural light from two windows, framed by privacy curtains. A bedside table with minimal decor sits adjacent to the bed, enhancing the serene ambiance.
Apartment in Downtown Toronto
5 out of 5 average rating, 41 reviews

Luxe 3BR - 1560 sq.ft. CN Tower View, Safe, Bidet.

Our elegant place is located in the heart of downtown Toronto in a step of the lively and trendy Bloor/Yorkville area. The unit is perfect for international visitors, families, and business travellers. About the unit: ➜ 1560 sqft corner signature suite ➜ Views of the CN Tower ➜ Keyless 24HR self check-in ➜ Located just steps from Yorkville, an upscale restaurant and shopping district in DT. ➜ 150 meters from the Subway station ➜ Walk score of 98 - Excellent! ➜ Transit score of 100 - Excellent!

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 cozy living room is presented with a large floral artwork adorning one wall. A comfortable sofa with decorative cushions faces a television, while a wooden coffee table is positioned in the center. Light filters softly through the lace curtains, illuminating the space.
Home in Downtown Toronto
4.94 out of 5 average rating, 129 reviews

Artist's Lovely Cabbagetown Century Home Downtown

Located in a peaceful historic neighbourhood, you'll feel right at home in this Arts and Crafts residence featuring authentic finishes, hardwood floors, private courtyard garden, and deck. A quaint cottage-like gem filled with the artist's original works. Fast hi-speed Wi-Fi, premium cable. One block from streetcars. Many award-winning restaurants, jazz bars and gourmet shops. Walking distance to the core of Toronto's downtown. Street parking and city lot on the block. Superhost for 11 years.

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
4.94 out of 5 average rating, 216 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
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 Midtown
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
Home in Midtown
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, 109 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
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 Toronto
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.

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 Downtown Toronto
4.93 out of 5 average rating, 182 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.

Top guest favourite
Home in Midtown
5 out of 5 average rating, 11 reviews

1200 sq ft Private Space in Heart of Forest Hill

* 1200 sq ft of fully private space over 2 storeys * Upstairs: 1 bedroom (king bed), bathroom w/ 2 sinks, TV, desk, laundry * Downstairs: Pull out couch (full/double bed), bathroom w/ shower * 100” TV w/ surround sound Sonos speakers * Full kitchen, high end appliances * FREE parking * Ideal location: Steps from St Clair streetcar, short walk to Line 1 & Line 2 subways, in a famous, quiet neighbourhood in Toronto (Forest Hill), short walk to Spadina Village or shops on Yonge St

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, 62 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 modern kitchen and living area are depicted, featuring sleek cabinetry and stainless steel appliances. A spacious island with seating for three is situated at the center. The adjacent lounge area is furnished with a light-colored sectional sofa, and a large wall-mounted TV is visible.
Home in Toronto
4.96 out of 5 average rating, 45 reviews

The Riverdale Laneway Suite

Welcome to our stylish new laneway suite nestled in the beautiful Neighbourhood of Riverdale. This modern new build offers two bedrooms, two bathrooms, a fully equipped kitchen and spacious living space. Perfect for solo travelers, couples or small families. Enjoy the vibrant neighbourhood filled with cafes, shops, parks and and attractions just steps away. Whether you are here for business or leisure our laneway provides the perfect home base for your stay in Toronto.

Popular amenities for Rosedale holiday rentals

When is the best time to visit Rosedale?

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Avg. price$148 SGD$163 SGD$139 SGD$183 SGD$185 SGD$186 SGD$174 SGD$189 SGD$175 SGD$160 SGD$143 SGD$161 SGD
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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 $38 SGD 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    100 of Rosedale holiday rentals include wifi 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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