Vacation rentals in Church-Wellesley, Old Toronto

An ice skating rink, bustling with skaters, is framed by modern skyscrapers and the historic Old City Hall. A large illuminated sign spelling 'TORONTO' stands on one side, while a bridge arches over the rink, linking the lively scene to the surrounding architecture.

4.88 out of 5 average rating, 41 reviews

Entire and cozy large studio in Downtown, Toronto

❇️Large renovated studio close to 3 downtown subway stations. LOCATION, and convenience: Although the apartment is in the heart of downtown, the street is very cozy surrounded by houses, trees and parks. Close to all tourist spots such as Dundas Square, Eaton Center, ROM museum, CN TOWER ❇️everything for your daily needs: Tv with Netflix, Amazon, and Amazon Prime. Espresso machine, French press and electric kettle. Workspace desk, complete kitchen (cooking spices gently provided), AC, and Heater

The living area features a neutral-toned sofa positioned adjacent to a dining table with two modern stools. A floor lamp provides soft light, while a kitchenette is visible in the background, showcasing sleek cabinetry and appliances. Warm wooden flooring contrasts with the light walls.

4.9 out of 5 average rating, 29 reviews

Cozy 1 BR @Bloor/Yonge by subway

Experience downtown Toronto living at its finest in this bright unit located in a Yorkville condo. Situated across from the prestigious W Hotel, convenience is at your doorstep. Enjoy the upscale shopping of Bloor Street's Mink Mile and the diverse dining options on Yonge Street. The Bloor/Yonge subway station is a short walk away, providing easy access to the rest of Toronto. This unit boasts a 100% walk and transit score. Experience the best of Toronto living in this centrally located unit.

4.97 out of 5 average rating, 62 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!

A modern living space is featured, showcasing a white sofa adorned with a yellow accent pillow. A marble coffee table sits on a patterned rug, while a sleek television is mounted on the light-colored wall. Natural light enters from a nearby window, enhancing the airy atmosphere.

4.91 out of 5 average rating, 22 reviews

Elegant Downtown Condo for the Perfect Getaway

Start your Toronto stay with comfort, style, and unbeatable convenience. Stay connected with blazing Bell 1.5 Gbps Wi-Fi, unwind with two 55” 4K TVs and bamboo therapeutic beds, and take in skyline views at the seasonal rooftop pool. Enjoy 24/7 concierge service and the convenience of an on-site Rabba store. Free street parking after 9PM. Steps to transit, shops, and dining — just 8 min to Dundas Square and Eaton Centre. Ready to experience Toronto like a local? We’d love to host you!

Hotel room in Downtown Toronto

A contemporary bathroom is designed with a glass shower enclosure and modern fixtures. A sleek vanity with a sink is positioned next to a toilet. Soft lighting is provided by an illuminated mirror, creating a bright and clean atmosphere.

4.79 out of 5 average rating, 86 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!

Two black valet signs are positioned prominently on a concrete surface, indicating designated valet parking. An upscale vehicle is partially visible in the background, and a modern building's entrance is seen behind the signs, characterized by a sleek architectural design.

4.93 out of 5 average rating, 169 reviews

Beautiful 1 Bedroom Yorkville Condo (IG-hotspot)

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.

5 out of 5 average rating, 50 reviews

The One in Yorkville-Previously Four Seasons Hotel

Our chic apartment in the heart of Yorkville is within a five-minutes-walk to ROM and Gardener museums, University of Toronto, libraries, theatre, bookstore, parks, subway stations, church, Whole Foods, and all retail stores, from Chanel, Dior, Holt Renfrew, to COS, Sephora, and Winners. Nestled among Park Hyatt and Hazelton Hotel, our building was previously the historic Four Seasons Hotel, and the upscale area around it is bustling with cafes, restaurants and art galleries.

A modern bathroom features a walk-in shower with a glass door beside a white toilet. A sleek vanity with a rectangular sink sits under a backlit mirror. Light grey tiles cover the floor, while wooden shelves add functional storage space.

4.71 out of 5 average rating, 14 reviews

Cozy One Bedroom Condo Yonge/Bloor

- 5 mins walk to Bloor-Yonge Subway Station - 5 mins walk to nearby grocery store, restaurants, LCBO - 10 mins walk to vibrant Yorkville community with Royal Ontario Museum, Art Gallery and Luxe Boutiques - 30 mins to Downtown Toronto, CN Tower, Scotiabank Arena and Roger’s Centre by subway - Full Kitchen with Stainless Steel Appliances and Kitchen Essentials - Hotel-equivalent Pillows, Liens, Sheets and Towels and Bathroom Essentials

A rooftop terrace offers stunning views of the city skyline, featuring a blend of modern skyscrapers. Black metal tables and chairs provide seating, while lush planters add greenery around the edges, creating an inviting outdoor space for relaxation.

4.97 out of 5 average rating, 132 reviews

Luxury One Bedroom In The Heart Of DT/Next To SubW

Enjoy a stylish experience at this centrally located place. Super central steps away from Wellesley Subway station. This renovated suite looks right onto Yonge St. With many restaurants and stores right outside the front door everything is within arms reach. Enjoy the cozy living room with a massive flat screen, luxurious beddings and a modern kitchen that is fully stocked for all your needs.

A panoramic view of Toronto's skyline is showcased, featuring a mix of modern skyscrapers and historic buildings. Lush greenery punctuates the urban landscape, while distant landmarks are visible under a clear blue sky, complemented by soft clouds.

5 out of 5 average rating, 4 reviews

Urban Escape in Prime Location + 1 Free Parking

Escape to this modern condo in Toronto's charming Cabbagetown, surrounded by scenic parks, local cafes, and the vibrant Distillery District. The condo is professionally decorated, offering a stylish and private retreat with no shared spaces. Thoroughly cleaned between each guest, it provides a fresh, inviting atmosphere—perfect for exploring the city or simply relaxing in your own space.

A scenic balcony view captures the Toronto skyline, showcasing a variety of high-rise buildings under a clear blue sky. The expansive cityscape is complemented by a glass railing, providing an unobstructed perspective of urban life below.

4.96 out of 5 average rating, 24 reviews

Modern High Rise Chic Studio - Downtown Toronto

Experience the heart of Toronto in our modern studio condo at Yonge and College! This perfect retreat is designed for those looking to enjoy city life with comfort and style. Whether you’re here for business or leisure, our fully equipped studio offers a prime location, stunning city views, a TTC subway station right outside, and easy access to top attractions.

4.92 out of 5 average rating, 122 reviews

A charming heritage home features a welcoming entrance with a wooden staircase leading to the front door. Lush greenery surrounds the property, including leafy shrubs and a small red-leafed tree. Large windows are visible, providing light to the inviting facade.

Home in Downtown Toronto

Heritage House all to Yourself! 1BR 3BA 2 Liv Rms

Beautiful detached heritage home on tree lined street in downtown Toronto. Wellesley Subway half block away. 1 bedroom w/ensuite, formal dining room, living room, kitchen w/breakfast room, separate TV room, and about a gajillion books to read :) We also have no hidden cleaning fees (don’t you hate those??)

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Popular amenities for Church-Wellesley, Old Toronto vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Church-Wellesley, Old Toronto's top sights

University of Toronto32 locals recommend

Toronto Eaton Centre392 locals recommend

Royal Ontario Museum513 locals recommend

Art Gallery of Ontario356 locals recommend

Yonge-Dundas Square173 locals recommend

Yorkville176 locals recommend

Other great vacation rentals in Church-Wellesley, Old Toronto

The exterior of a charming brick residence is showcased, featuring arched windows and a large entrance flanked by greenery. Mature trees provide shade, while the wrought iron fence outlines the front garden, enhancing the inviting atmosphere of the home.

4.93 out of 5 average rating, 138 reviews

The Winchester, Modern Bedroom Suite

MandyRating, 5 stars2 days ago

Andrew was a great host. His home was upscale, comfortable and easy to travel from. Within easy walking of restaurants and public transportation. Wicklow the dog is a bonus feature! Choice of firm or soft pillows on the bed was appreciated. Full length mirror in bedroom nice touch. Especially enjoyed the plush bathmat and towels in the very clean, well-supplied bathroom. Would stay here again!

4.98 out of 5 average rating, 249 reviews

Beautiful Loft in Victorian House with Hot Tub

NoelleRating, 5 stars6 months ago

We couldn’t have asked for more. Absolutely beautiful interior. Very comfortable bed and crisp clean linens. Walkable to Distillery Winter Village. Rooftop cedar hot tub. Coffee Nextdoor at the Sumach Cafe. We will be back!

A private outdoor deck is surrounded by lush greenery and features a brown wicker seating area. Colorful flowers bloom in planters, and wooden fencing offers privacy while allowing light to filter through. The space provides a tranquil setting for relaxation.

4.87 out of 5 average rating, 105 reviews

DT Toronto Sunny Suite in Historic Cabbagetown

MohammadRating, 5 stars1 month ago

I had a great stay! The place was clean, quiet, and exactly as described. The host was kind and responsive, and everything went smoothly. I’d definitely recommend staying here. Thank you for the hospitality!

A private back patio is featured, illuminated by string lights. A wooden picnic table is positioned on the dark wooden deck, surrounded by brick walls and a fence. An alleyway is visible in the background, providing access to the side of the home.

4.95 out of 5 average rating, 215 reviews

Cozy suite in the heart of Toronto (no kitchen)

Ella-KatrinRating, 5 stars1 week ago

Had a great stay!

A modern kitchen is highlighted by sleek cabinetry and open shelving. A large window allows natural light to brighten the space, revealing a snowy outdoor view. Countertops are adorned with cooking essentials, including a bouquet of flowers and an array of utensils on display.

4.84 out of 5 average rating, 103 reviews

A Sunny Room in a Victorian House (Cabbagetown)

CindyRating, 5 stars2 weeks ago

BOOK BOOK BOOK THIS PLACE‼️ I booked this place for my dad for few days! The host was very responsive and helpful they made sure to check in if my dad checked in okay! They remained in constant communication with me My dad described them as “very friendly and pleasant” he felt very comfortable and at home! Where the unit is located is VERY convient it’s accessible to many amenities(supermarkets stores, tourist spots, convient stores) he could easily walk anywhere he wanted. I thought he would need an uber but honestly everything is walkable 5-10 minutes The place itself was very comfortable modern, sleek and aesthetically pleasing you could tell it had been recently renovated. The main shared spaces are filled with everything you need! Each room has bathroom assigned to it! Which I found to be extremely convenient Overall this place is value for your money! I would recommend anyone staying here if your coming for short visit and a convient location without comprising comfort!

4.84 out of 5 average rating, 19 reviews

*Downtown Condo Private Room with City Views*

MiladRating, 5 stars1 month ago

I had a great stay at Brent’s place. It was quiet, clean, and exactly as described. Brent was a friendly and respectful host—communication was smooth and easy throughout. Would definitely recommend staying here!

A bright view of downtown Toronto is visible through the large windows. Skyscrapers and residential buildings are framed against a clear blue sky, showcasing the cityscape and surrounding greenery.

5 out of 5 average rating, 69 reviews

Private Room with a View

Ashiyah MoneRating, 5 stars5 days ago

My stay was amazing! He made me feel at home, I explained it was my first time out of the country and he gave great recommendations. He was also just as equally friendly to my cousin when he stopped by. Overall amazing and I do plan on coming back and I might just rebook the Airbnb because it was so welcoming.

A welcoming living area is filled with natural light from large windows adorned with soft drapes. Comfortable seating is arranged around a glass coffee table, with potted plants and decorative accents enhancing the space. A glimpse of the city skyline is visible through the glass.