
Holiday houses in Rosedale
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Rosedale
Guests agree: these stays are highly rated for location, cleanliness and more.

Huge 2 Storey Loft W designer furniture and art
This one of a kind penthouse in downtown Toronto has 18ft high ceilings and furnished with designer furniture and art. No parties or loud gatherings are allowed here they will get cancelled. Only 4 people are allowed up to the unit total and is monitored by 24h concierge, they will check in each guest and only allow 4 up. 3 bedrooms one upstairs just a bed 1 king bed and one queen bed upstairs. The couch could sleep 1 ontop as well but is not a bed. Fire place and true luxury art with a 75" TV

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.

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.

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.

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.

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

Stylish 1870s Home near Distillery District & Old Toronto
Steps from the Distillery District this Top 1% listing is a beautifully restored 1870s row-house that blends historic charm with modern refinement. Thoughtfully designed throughout, it’s located at the Distillery District, 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

Modern and bright private suite.
Enjoy a newly built, professionally designed, roomy 1-bedroom basement apartment in East York Toronto. Conveniently located near the Danforth, Woodbine Beach, parks, and trails, the apartment is a short bus/subway ride or a 15 min drive from Downtown Toronto. Self-contained and spacious, it offers a fully equipped kitchen, new laundry facilities, a queen-sized bed, ample storage, and plenty of natural light.

The Peony Loft - a Modern Take on the Victorian
Built in 1893, this classic Toronto Victorian home will be a relaxed introduction to city life. Enjoy the upper living space, laid out over two floors, with a gorgeous private, beautiful furnished sky deck with a view of Toronto's exciting skyline. Experience the restaurants, pubs & nightlife of Toronto's College St. neighbourhood of Little Italy, all within walking distance of your front door.

Bright, Stunning Victorian Townhouse in the Annex
Newly renovated, 3 level, 2-bedroom sun-filled unit, situated in the Annex. Brick fireplace, central air conditioning and heating, wooden floors and exposed brick. Steps away from Bloor St, coffee shops, restaurants, shops, galleries, parks and much much more. Short walk to Bathurst and Spadina Subway, Casa Loma, Yorkville, University of Toronto, and museums.
Popular amenities for Rosedale holiday rentals
Other great holiday rentals in Rosedale

Leslieville Luxury Home 4BR Entertainer's Dream

Prestigious Rosedale Neighbourhood 4 BR Home

Gem house/10 min to downtown/3BR/Subway/2 Parking

Gem house/5BR/3.5Bth/4 Parking/15 min to downtown

John's Island House

Luxe Forest Hill Retreat

Yorkville Skycrest Penthouse | King Bed | Gym+Pool

Bright Two Story Loft, Downtown TO, FREE Parking
When is the best time to visit Rosedale?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $205 NZD | $207 NZD | $234 NZD | $242 NZD | $246 NZD | $247 NZD | $230 NZD | $251 NZD | $232 NZD | $212 NZD | $190 NZD | $213 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 $51 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 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
Destinations to explore
- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Enercare Centre
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Distillery District
- Harbourfront Centre
- Nike Square One Shopping Centre
- Toronto Eaton Centre
- Exhibition Place
- Toronto Zoo
- Trinity Bellwoods Park
- Niagara Falls State Park
- Financial District
- Massey Hall
- Downsview Park
- Casa Loma
- Dufferin Grove Park
- Casino Niagara
- Lakeridge Ski Resort




