Holiday rentals in Church-Wellesley

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Top-rated holiday rentals in Church-Wellesley

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Flat in Discovery District
4.87 out of 5 average rating, 31 reviews

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.

Guest favourite
An open-concept living space is highlighted by large windows and high ceilings. A dining table with blue chairs sits beside a stylish kitchen. A comfortable sectional couch is visible in the living area, while an eye-catching artwork adorns the wall. Stairs lead to the lofted bedroom.
Flat in Saint James Town
4.97 out of 5 average rating, 78 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!

Top guest favourite
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.
Flat in Saint James Town
5 out of 5 average rating, 30 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.

Guest favourite
A modern bedroom features a plush green bed with layered bedding in shades of green and blue. A piece of framed artwork hangs above the bed. Natural light filters through large glass doors, which open to a city view, while dark curtains frame the windows.
Flat in Downtown Toronto
5 out of 5 average rating, 26 reviews

Pleasant 1BR Sofa Bed Close to UofT

Welcome to our modern urban retreat in the heart of downtown Toronto, situated next to the lively Yorkville area and the esteemed University of Toronto. Experience the ideal mix of luxury and convenience in our elegantly furnished apartment, featuring breathtaking city views. Discover world-class shopping, dining, and cultural attractions just moments away. Our space comfortably accommodates three guests, offering a plush Queen bed in the bedroom and a pullout sofa bed for an additional guest

Top guest favourite
Flat in Church-Wellesley
4.97 out of 5 average rating, 35 reviews

Clean and Bright 2 Bed w/Parking & Gym

Stay close to everything that makes Toronto great in the heart of downtown. This 2 bed, 1 bath offers an abundance of light to greet you each day + great amenities. I stay here with my infant daughter from time to time so this unit is CLEAN CLEAN CLEAN. Small collapsible baby bathtub and baby doc cushion for your use if travelling with an infant. Take advantage of the city’s public transportation one minute from your doorstep . Access to the condo gym. Garage parking on the property.

Guest favourite
A spacious room features a comfortable bed and a sitting area with elegant leather chairs. A desk is positioned by the window, offering natural light. Light hardwood flooring complements the room's neutral color scheme, while a piece of artwork adds a touch of color.
Flat in Yorkville
4.92 out of 5 average rating, 25 reviews

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.

Top guest favourite
An outdoor seating area is showcased, featuring a comfortable couch adorned with patterned cushions. Flanking the couch, two red chairs face a wooden fence, while a decorative lantern and potted plants add touches of greenery, highlighting the inviting atmosphere of this private space.
Home in Cabbagetown
4.94 out of 5 average rating, 588 reviews

Comfy Oasis In Historic Downtown Neighborhood

According to Airbnb, we are "One of the most beloved homes on Airbnb". Now in the top 5% of all listings on AIRBNB. Superhosts for 10 years! This renovated guest house features an open-plan kitchen, a spiral staircase to a beautiful and open loft suite, with custom furniture and decorating accessories (1 bed + 1 sofabed). Enjoy the beautiful garden in the summer, and sip any of the more than 15 different complimentary teas and coffees we offer. This guest house is FULLY equipped.

Superhost
A modern living space features large windows that overlook the city skyline. Stylish furnishings include a spacious couch with decorative pillows, yellow dining chairs at a glass table, and a sleek kitchen with a dark countertop. Natural light brightens the open layout.
Flat in Yorkville
4.9 out of 5 average rating, 20 reviews

Beautiful 1BR Condo Coveted Yorkville!

Welcome to our stylish and luxurious Yorkville condo! Immerse yourself in the heart of Toronto's most upscale neighbourhood, surrounded by top-rated shopping, renowned restaurants, and cultural attractions. This chic retreat offers modern amenities, elegant design and a prime location for an unforgettable stay in a newly-constructed building. ➜ Approx. 500ft² / 56m² of space ➜ Highspeed WIFI ➜ In-unit washer & dryer ➜ Fully equipped kitchen ➜ Steps to Bay & Museum subway stations

Superhost
A spacious bedroom is presented with large windows offering panoramic city views. A comfortable bed is complemented by stylish bedding and a decorative throw. A bedside table and lamp enhance the functionality, while a modern chair adds to the overall decor.
Flat in Church-Wellesley
5 out of 5 average rating, 3 reviews

CN Tower View - 2BR - Free Parking - Pool/Gym

Our spacious 2BR suite is located in the heart of Toronto, with panoramic skyline and CN Tower views. The unit is perfect for international visitors, families, and business travellers. ➜ Located 1 min walk to College/Yonge subway station ➜ Easy access to CN Tower, Metro Toronto Convention Centre, Rogers Centre, Scotiabank Arena, Union Station ➜ View of the CN Tower ➜ 24HR self check-in ➜ 1 FREE parking spot ➜ Walk score of 100 - Excellent! ➜ Transit score of 100 - Excellent!

Superhost
A spacious living area features a red sofa, a coffee table, and a dining table surrounded by black wire chairs. A large mirror reflects the light fixtures and the white cabinetry in the background, while a colorful piece of artwork adds a pop of color to the wall.
Guest suite in Cabbagetown
4.84 out of 5 average rating, 133 reviews

Spacious and Modern Garden Suite Studio

Bright, modern and large studio of nearly 700sqft/70sqm in North America’s largest Victorian district just minutes from Yonge Street, Ryerson, and the Village. Great for those who don’t want the hassle or sterility of condo rentals. Queen Murphy bed with extra deep mattress plus a Bensen sleeper sofa that sleeps one adult or two children. Full shutters that block out light or let some in while maintaining privacy during the day.

Top guest favourite
The exterior of a detached heritage home is showcased, featuring a brick façade and large windows. The entrance is framed by vibrant orange flowers and lush greenery. A yellow awning extends over the front door, adding a cheerful touch to the welcoming ambiance.
Home in Church-Wellesley
4.92 out of 5 average rating, 137 reviews

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??) and our house keeper takes care of sheets, towels, garbage, cleaning etc when you leave.

Guest favourite
Flat in Yorkville
5 out of 5 average rating, 8 reviews

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.

Popular amenities for Church-Wellesley holiday rentals

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Quick stats about holiday rentals in Church-Wellesley

  • Total holiday rentals

    Explore 350 holiday rentals in Church-Wellesley

  • Nightly prices starting at

    Church-Wellesley holiday rentals start at £15 per night before taxes and fees

  • Verified guest reviews

    Over 11,410 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 60 rentals that welcome pets

  • Holiday rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wifi availability

    340 of Church-Wellesley holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Church-Wellesley rentals

  • 4.8 Average rating

    Church-Wellesley stays are highly rated by guests – averaging 4.8 out of 5!

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