Vacation rentals in Rosedale

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Top-rated vacation rentals in Rosedale

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Top guest favorite
The exterior of the laneway house features a modern design, characterized by large windows and a dark facade. It is surrounded by mature trees and a well-maintained yard, creating a serene atmosphere. A stone pathway leads to the entrance, inviting guests into the space.
Home in Parkdale
5 out of 5 average rating, 48 reviews

Stylish Oasis: an architect's unique laneway house

Come and experience our laneway house in the heart of Parkdale, Toronto! This brand new (2022) laneway house has been beautifully designed by the homeowner/architect with amazing attention to detail. It is modern and bright with windows on all 4 sides of the house. It’s inviting, clean and nestled in a park-like setting. It’s also completely private and quiet. Close to Roncesvalles Ave, High Park, Sunnyside Beach, Queen Street and venues such as BMO Field, Exhibition, and the Budweiser Stage.

Top guest favorite
A spacious living room is filled with natural light from large windows, offering city views. A large sectional sofa with soft cushions is placed around a glass coffee table. Occasional chairs with a distinctive pattern complement the elegant decor, highlighted by a decorative chandelier above.
Apartment in Saint James Town
5 out of 5 average rating, 26 reviews

Penthouse * Rare * Stunning Views * 2500 sq ft

Be greeted to spacious luxury in the heart of downtown. You'll be surrounded by a tasteful blend of traditional and high end decor - with some pieces dating to early 1900's Europe. Unwind after a long day in the deep soaker tub in front of the fire, while gazing at the city scape just outside the window. Feel at home especially if you desire a chef's kitchen, large and open entertaining spaces with 2 fireplaces, 2 bedrooms, 2.5 bathrooms & private home office. 1 underground parking space incl.

Top guest favorite
A spacious studio suite showcases a plush queen-sized bed with soft linens and pillows. A comfortable living area includes a smart TV and a cozy gas fireplace. A dining table with white chairs sits invitingly, and plants add a touch of greenery to the decor.
Home in Cabbagetown
5 out of 5 average rating, 57 reviews

Private, Peaceful Suite w/ Conveniences Steps Away

*No Cleaning or Service Fees* Welcome to this bright, private suite with its own separate keyless entry, located on the upper floor of a heritage home. Enjoy plenty of natural light, a cozy gas fireplace, and two balconies. Equipped with a full kitchen, in-suite laundry & A/C, this suite offers a perfect blend of comfort and convenience. Food & Shopping: 200m-450m TMU: 1.8 km U of T: 2.6 km Dundas Square: 2.7 km Please note: The suite is located on the 3rd floor, and access is via stairs.

Guest favorite
Bright living area features large windows with city views, allowing ample natural light. A gray sectional sofa is adorned with decorative pillows, complemented by a warm throw. A dining table with modern chairs sits nearby, beside a stylish coffee table displaying books and greenery.
Condo in Yorkville
4.95 out of 5 average rating, 75 reviews

Prestigious Yorkville Condo, Free Valet Parking

High-end buildings in the area with Free Valet Parking through out your stay, doesn't matter how many times you have to leave and come back. Enjoy a stylish experience at the heart of Downtown Toronto. Best restaurants, cafe's, Museum and shopping experience you can have. Less than 1 min walk to Bay street subway station. 5 min walk to Royal Ontario Museum, Queens park, University of Toronto. 2 mins walk to Prada, Cartier, Tiffany's, Chanel, LV, Harry Rosen, Holt Renfrew and many more!

Top guest favorite
A garden path lined with stepping stones leads to a view of the Toronto skyline across the water. Green grass and plants surround a patio table and chairs, providing a serene setting with trees framing the picturesque scene.
Cottage in Toronto
4.94 out of 5 average rating, 71 reviews

Toronto Island Cottage

This beautifully furnished, bright, and airy cottage is located just eight minutes south of the city, on the picturesque Toronto Island. This is a unique opportunity to experience all that the islands offer in a stylish setting. Perfect for a staycation or vacation, the cottage is well-equipped with everything you need to make the most of your time. The serene community is accessible only by ferry or water taxi. The view of the Toronto Harbour and skyline is absolutely epic – enjoy!

Top guest favorite
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
4.94 out of 5 average rating, 157 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.

Superhost
The modern kitchen features sleek cabinetry and stainless-steel appliances, including a microwave and oven. A spacious island provides seating and workspace. The living area includes a sectional sofa and a coffee table, with large windows allowing natural light to fill the space.
Hotel room in Church-Wellesley
4.77 out of 5 average rating, 146 reviews

Town Inn Suites

Discover your urban retreat in this spacious 500-square-foot room in downtown Toronto, just a short walk from Yorkville. This suite features a king size bed, fully equipped kitchen, ideal for meals, along with a separate living area filled with natural light and a cozy dining space. Enjoy the privacy of a separate bedroom and a well-appointed bathroom. This is the perfect place for extended stays, just a 5-minute walk to the Yonge-Bloor subway station—ideal for exploring the city!

Top guest favorite
The living area features a modern design with a comfortable sofa accented by patterned pillows. A marble dining table is surrounded by elegant chairs. A striking chandelier hangs above, while a large round mirror reflects the ambient light from windows dressed in soft curtains.
Home in Corktown
4.99 out of 5 average rating, 236 reviews

Stylish 1870s Home near Distillery District & Old Toronto

“Rated a Top 10 listing by BlogTO and frequently featured as a must-stay in Toronto. Love thoughtful details? You’ll find them here in this stylishly remodeled 1870s rowhouse. Start your day at St. Lawrence Market, wander through the pedestrian-friendly Distillery District, and explore nearby cafés, restaurants, and bars. In the evening, retreat to the plush, charcoal-hued bedroom and drift off under the glow of a tiered Restoration chandelier. The perfect Toronto stay awaits.”

Top guest favorite
A stylish living room is filled with various plants and natural light. A comfortable sofa is flanked by two chairs, with a small coffee table in front. A large artwork is displayed on the wall, and a decorative rug is laid on the floor.
Apartment in Annex
5 out of 5 average rating, 42 reviews

Grande Victorian Retreat

Enjoy a stylish, luxury experience at this centrally located apartment on the main floor of a Victorian home. Walking distance to CasaLoma, Royal Ontario Museum, University of Toronto, Yorkville Village Shopping! Only a 2 minute walk to the TTC. The space Living Room: Smart TV and High-speed internet. Bedroom: Queen-sized bed, large walk-in closet, Smart TV. Kitchen: Fully-stocked to make your extended stay feel like home. Bathroom: Large walk-in shower, Washer dryer unit.

Guest favorite
The living area features large windows that allow natural light to fill the space, highlighting a comfortable sofa and two armchairs. A glass coffee table is positioned in the center atop a patterned area rug, complemented by a tall bookshelf and decorative elements.
Condo in Saint James Town
4.91 out of 5 average rating, 69 reviews

Rare Luxury 3 Bedroom Residence -Yonge/Bloor Area

Welcome to Luxurious Residence. This rare and stunning 1600 sq. foot 3 bedroom condo comes with luxury finishes, soaring 11 foot ceilings and large windows. Gourmet kitchen with all essentials is perfect for entertainment. In suite laundry and locker. Underground parking available. Stay in the heat of city near Bloor street shops, Rosedale ravine and Yorkville Village. Subway station across the street. First class amenities such as sauna, gym, 24 hour concierge.

Top guest favorite
A cozy sleeping area features a king-size bed with a crisp white comforter. A striped headboard serves as a backdrop, complemented by decorative pillows. A nightstand holds a stylish lamp and decorative items, while soft peach tones accentuate the space.
Guest suite in Cabbagetown
5 out of 5 average rating, 44 reviews

Boutique Suite in Historic Cabbagetown (King Bed)

Stay in a beautifully renovated private suite in Toronto’s iconic Cabbagetown—home to the largest collection of Victorian homes outside of England. This stylish, hotel-style lower level suite has its own entrance, ensuite bathroom, kitchenette and a Palm Springs-inspired design. Located in the heart of the city, guests can access many destinations including downtown, the Distillery District, Yorkville, Danforth Greek Town, Leslieville and Riverdale parks.

Superhost
Apartment in Toronto
New place to stay

Bright & Modern Retreat in Cabbagetown

Enjoy a private and professionally decorated condo nestled beside historic Cabbagetown. This stylish retreat is professionally cleaned between every guest to ensure a spotless, welcoming stay. Explore charming Victorian streets, local boutiques, and cozy cafes, or visit nearby attractions like Riverdale Farm, Allan Gardens, and the Distillery District. Perfectly located for both relaxation and city adventures.

Popular amenities for Rosedale vacation rentals

When is the best time to visit Rosedale?

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Quick stats about vacation rentals in Rosedale

  • Total vacation rentals

    Explore 110 vacation rentals in Rosedale

  • Nightly prices starting at

    Rosedale vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 2,700 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Rosedale vacation 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

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