
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.

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.

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.

Stylish 1870s Home near Distillery District & Old Toronto
Visiting for fifa? Stop here...Steps from the Distillery District downtown, this Top rated listing is a beautifully restored 1870s row-house (townhouse) that blends historic charm with modern refinement. Thoughtfully designed throughout, it’s located downtown also close to 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

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.

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!!!

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 :)

Admire City Views from Bed at this Chic Apartment
The critics have spoken! This five-star rated, professionally designed unit offers a fresh, functional, and beautifully curated living experience. Every piece of artwork and each accessory has been thoughtfully selected to enhance comfort, style, and positive energy throughout the space. This spacious one-bedroom, one-bathroom suite features a fully equipped kitchen, open living and dining areas, and a versatile den — perfect for working remotely or relaxing after a day in the city.

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.

Beautiful 1 Bedroom Yorkville Condo w/ Parking
Pamper yourself with everything Yorkville has to offer with this professionally decorated, NYC inspired condo at the heart of Toronto's most exclusive address with complimentary valet parking. Queen size bed, sofa bed in living room, 2 person bar table, work station and a 55" Smart TV to accommodate all your needs. Contemporary art by local artist throughout with high end furniture and Miele appliances. South facing lake/city views through expansive floor to ceiling windows.

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)

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.
Popular amenities for Rosedale holiday rentals
Other great holiday rentals in Rosedale

Private Balcony, Near CN Tower and Subway

Modern City Stay | Prime Location & Views

25th Floor Skyline Views • Free Parking • FIFA2026

Stylish Loft in Midtown Toronto

Modern Midtown Manor

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

Cabbagetown Victorian Restored to Designer Dream Oasis

Luxe 3BR - 1560 sq.ft. CN Tower View, Safe, Bidet.
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
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
- Harbourfront Centre
- Nike Square One Shopping Centre
- Distillery District
- Toronto Eaton Centre
- Niagara Falls State Park
- Exhibition Place
- Downsview Park
- Toronto Zoo
- Trinity Bellwoods Park
- Financial District
- Casa Loma
- Niagara Falls
- Massey Hall
- Scarborough Town Center
- York University





