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
Apartment in Discovery District
4.88 out of 5 average rating, 33 reviews

Luxe Cozy Downtown 1BR Condo w/Views

Welcome to your 1-bedroom luxurious high-floor retreat in the heart of downtown Toronto! All just steps from Bay & College What You’ll Love: • High floor with city skyline views • Extra tall ceilings & full-height windows • Bright and airy space with abundant natural light • Fully equipped kitchen & in-unit laundry • High-speed Wi-Fi&Smart TV • Walk Score 99 – subway, U of T, Eaton, Restaurant all within minutes Perfect for couples, or solo traveler who want premium comfort in a prime location.

Top Guest favourite
Guest suite in Playter Estates-Danforth
5 out of 5 average rating, 17 reviews

Danforth Nook - Laundry included onsite

Enjoy easy access to everything from this centrally located home base for 2 adults, 1 child. This lower unit boasts all you need for a stay in the city. Just around the corner from Chester TTC subway station, and the thriving heart of The Danforth, this home away from home has all you need for rest through your stay. Self-check in at our side entrance takes you down 6 steps to your own entry way into a full kitchen, washer/dryer, washroom, queen bed, couch, TV, wifi, & a small separate office.

Superhost
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
4.87 out of 5 average rating, 31 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
4.94 out of 5 average rating, 213 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
An open-concept living space is highlighted by large windows and high ceilings. A dining table with blue chairs sits beside a stylish kitchen. A comfortable sectional couch is visible in the living area, while an eye-catching artwork adorns the wall. Stairs lead to the lofted bedroom.
Apartment in Saint James Town
4.97 out of 5 average rating, 79 reviews

Bright Two Story Loft, Downtown TO, FREE Parking

Enjoy a STYLISH experience at Andre's CENTRALLY located home. A statuesque highrise tower with attached suites & lofts. This is your urban address overlooking a European style park, a short walk to the University of Toronto, Metropolitan University and Yorkville. Located in the heart of the city, steps from transit and grocery stores. Minutes from the financial and entertainment districts. A short walk to the Village and its nightlife. You'll have Toronto at your feet. FREE PARKING for 1 car!

Guest favourite
A spacious room features a comfortable bed and a sitting area with elegant leather chairs. A desk is positioned by the window, offering natural light. Light hardwood flooring complements the room's neutral color scheme, while a piece of artwork adds a touch of color.
Apartment in Yorkville
4.92 out of 5 average rating, 26 reviews

Centrally Located Haven

Quick access to all downtown venues from this perfectly located unit - entire apartment to yourself :) Enjoy Yorkville, Church & Yonge streets, the distillery district etc. Restaurants, groceries, and a subway station all within walking distance. The world's at your fingertips. ! Perfect WFH space with high speed internet Welcoming respectful guests who will be on the quieter side and won't disturb my neighbors. Building amenities (exercise room, laundry, etc) available upon request.

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, 169 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 Summerhill
4.93 out of 5 average rating, 58 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

Guest favourite
Apartment in Toronto
4.84 out of 5 average rating, 19 reviews

Modern & Sleek Condo Near Everything + 1 Parking

Located in Toronto’s historic Cabbagetown, this chic condo is the perfect spot for those looking to enjoy both the tranquility of green spaces and the excitement of downtown. Explore nearby attractions like the Distillery District and Allan Gardens, or relax in this professionally decorated, private condo. With no shared spaces and professional cleaning between each guest, your stay will be both comfortable and effortless.

Superhost
A living area is presented with two blue armchairs positioned beside a low coffee table. A flat-screen TV is mounted on the wall above a gas fireplace. Light filters in through a large window, illuminating built-in shelves filled with decorative items.
Townhouse in Yorkville
4.82 out of 5 average rating, 104 reviews

Stunning Yorkville Townhome Backing onto Park

Situated in the heart of Yorkville, this 3 bedroom 2.5 bathroom townhouse with views overlooking Ramsden Park, is the ideal oasis for families, couples, or people travelling for work. The space features a bright sun-filled interior featuring a gas fireplace, WIFI, Smart TV with all apps and fully equipped kitchen. The home backs onto green space with a wonderful back deck and eating area.

Guest favourite
Apartment in Yorkville
5 out of 5 average rating, 14 reviews

Chic Yorkville Condo • Sleeps 3 • Prime Location

Experience upscale city living in the heart of Yorkville. This stylish brand-new 1-bedroom condo offers modern finishes, luxury Miele appliances, and a fully equipped kitchen — perfect for business travelers, couples, or small families. Nestled in one of Toronto’s most desirable new developments, you’ll be steps from world-class dining, high-end shopping, and the best of downtown.

Guest favourite
Condo in Yorkville
4.95 out of 5 average rating, 21 reviews

Yorkville Luxury • 2BR Condo w/ Views + Parking

Experience upscale living in the heart of Yorkville. This stylish 2-bedroom, 2-bath condo features modern finishes, luxury Miele appliances, a wine fridge, Nespresso, and in-suite laundry. With 2 bedrooms plus a sofa bed, it comfortably sleeps up to 6. Relax on the balcony with city views, then step outside to world-class dining, designer shopping, and Toronto’s top attractions.

Popular amenities for Rosedale holiday rentals

When is the best time to visit Rosedale?

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Avg. price$200 NZD$202 NZD$228 NZD$237 NZD$240 NZD$242 NZD$225 NZD$245 NZD$227 NZD$207 NZD$185 NZD$209 NZD
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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 $50 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,960 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

    110 of Rosedale holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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