Holiday rentals with a fireplace in The Annex, Old Toronto

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Top-rated rentals with a fireplace in The Annex, Old Toronto

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Guest favourite

Guest suite in Toronto

4.96 out of 5 average rating, 392 reviews

Ossington Rowhouse + Private Garden

Relax with a glass of wine in your own backyard garden at this romantic urban cottage—a 700 sq ft pied-à-terre on two private floors of a designer's 4-level townhouse just off the Ossington strip. This calm oasis is perfect for couples or business trips, with high-speed internet and flexible work spaces. Cook in the fully equipped kitchen, or discover Toronto's best bars and restaurants a few steps from home. Explore the city easily with a 97 Walk Score and a transit stop right outside the door.

Guest favourite

Home in Pape Village

4.84 out of 5 average rating, 179 reviews

Private apartment in trendy Danforth neighbourhood

One bedroom basement apartment in a single family home with separate entrance. 7 minute walk to Pape subway and 10-15 minute subway to downtown. Danforth shops and restaurants close by. Bedroom with queen size bed, desk, and washer/dryer in a generous sized closet. Kitchen/living area includes a full kitchen with stainless steel appliances and quartz counter tops, a kitchen table, and a living area with a sofa bed. Bathroom with nice sized shower with glass enclosure. All newly renovated.

Top guest favourite

Flat in St. James Town

5 out of 5 average rating, 11 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 favourite

Guest suite in The Beaches

4.98 out of 5 average rating, 111 reviews

The Beaches- Bright Suite with Kitchenette

Beaches-Bright 1 bed basement suite with kitchenette, TV room with gas fireplace & full bathroom. High speed Bell Fibe Internet. Short stroll to beach, shops and restaurants. Small town charm by the water; only a 25 min. streetcar ride to downtown Toronto. Max 3 hr parking anytime on our street. Paid permit parking on Leonard Circle; Lee Ave, & Beaufort Rd among others from the City of Toronto. Unit is suited for a couple/1 person. No smoking in & on property. Laundry for stays over 7 nights

Guest favourite

Guest suite in Toronto

4.89 out of 5 average rating, 113 reviews

Loft-Style Private Studio Little Italy/Ossington

From the exposed brick, to original artwork, to massive private bathroom with double vanity, this basement suite in our home has been renovated and decorated to feel like a loft. The double bed is brand new with a 16" mattress sure to deliver an excellent night's sleep. You will find a brand new, 42" smart TV resting on a unique mantlepiece refashioned from an antique upright piano, as well as a kitchenette with convection oven/air fryer, Keurig coffeemaker, and stainless steel mini fridge.

Guest favourite

Flat in Yorkville

4.97 out of 5 average rating, 77 reviews

Luxury condo in Yorkville, Toronto, free parking

Welcome to your home at Yorkville Plaza in the heart of downtown Toronto! Formerly the Four Seasons Hotel Condo, this suite has been newly furnished. The main bedroom is full of natural light and the den serves as a second bedroom or office. The living room sofa can be turned into a huge bed. You can sit beside fireplace or cook in the kitchen; you can watch spectacular city views or enjoy comforts from smart TV to smart toilet. Walking around in the historical old York Village is joyful!

Top guest favourite

Guest suite in Toronto

4.95 out of 5 average rating, 117 reviews

Cozy apartment in the heart of Trinity Bellwoods!

You will enjoy easy access to the city from this centrally located place! Steps to Dundas street and nearby streetcar stop. A short walk to Little Italy, Ossington & Queen West! This apartment has all you need for a weekend getaway in the city! Kitchenette w/ fridge/freezer, coffee maker & microwave for quick breakfast prep, a spacious living room, a rain shower-head for a spa like shower experience and a comfy queen sized bed! Registration Number: STR-2208-GWRHHH Exp: 09-29-2025

Guest favourite

Townhouse in Summerhill

4.96 out of 5 average rating, 45 reviews

Stunning Upscale Toronto - Historic Home/ Hot Tub

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

Guest favourite

Home in Trinity-Bellwoods

4.96 out of 5 average rating, 56 reviews

Luxury Home in Trinity Bellwoods | Hot Tub

In the heart of Trinity Bellwoods, This gorgeous 2 Bed 1.5 Bath is light and bright and flows effortlessy from livng room, dining room and kitchen. The custom kitchen with gas range, stone counters and custom cabinets is a pleasure to cook and entertain. Primary bedroom also function as a sitting room so you can look out at the beautiful backyard; now with a large private hot tub! Downstairs you will find a gorgeous main bath with large walk in shower

Top guest favourite

Home in Palmerston

5 out of 5 average rating, 94 reviews

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.

Superhost

Apartment in Garden District

4.8 out of 5 average rating, 5 reviews

*Cozy* 1bed condo w/ pool & view DT Toronto

Located in the heart of downtown Toronto this one bedroom oasis is just minutes away from the iconic Dundas Square. This special place is close to everything, making it easy to plan your visit to Toronto. Sunny, modern and luxurious sitting over 30 stories high you will indulge in an unobstructed city and lake view

Top guest favourite

Home in Church-Wellesley

4.93 out of 5 average rating, 121 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??)