
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.

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.

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.

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.

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.

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!

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.

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.

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

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.

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.

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.

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
Other great holiday rentals in Rosedale

Stylish Downtown 1BR Condo | Balcony & City Views

Chic, Centrally Located 1 Bedroom Suite

Riverdale Suite Artist Retreat

Modern Yorkville Condo with Dedicated Makeup Room!

Private suite in Riverdale, 5 mins to the subway

Unique and stylish in The Danforth!

Stylish 1BR Haven Near Downtown Toronto

Panoramic City Views | Pool, Hot Tub & Gym Perks
When is the best time to visit Rosedale?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
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
Destinations to explore
- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- BMO Field
- Nike Square One Shopping Centre
- Harbourfront Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Financial District
- Massey Hall
- Niagara Falls State Park
- Casa Loma
- Dufferin Grove Park
- Lakeridge Ski Resort
- Toronto City Hall
- Downsview Park




