Holiday rentals in Old Toronto

Bright Suite in Little Portugal / Queen West

Our guest suite is bright, spacious & cozy - just down the street from The Drake Hotel. We're in the heart of Little Portugal - tons of amazing restaurants, shops, amenities & cafes in all directions. It’s a great launch pad to explore Queen west / Ossington / Parkdale / Trinity Bellwoods / Dundas West. *Check-in using the keypad on. We keep the space simple and very clean, all the linens & towels are cotton and you'll find organic coffee beans ready to grind + brew! *Pack+play bed available

Yorkville | Exec Kitchen | Office | Spa bathrooms

Tucked away on a tranquil street in Yorkville , this 19th-century gem places you steps from the city's most exclusive dining, shopping, and art galleries. Meticulously renovated, you'll enjoy high-end finishes --a Wolf range, Miele appliances, deep soaker tub and custom furniture. The spacious layout features 1 bedroom per floor for ultimate privacy. The home office ensures effortless remote work. When it's time to close your laptop, unwind on 1 of 3 patios, savoring serene city skyline views.

Sunny private home with garden and free parking

Entire home (not shared, no other tenants in house, no basement apartment ) with 2 bedrooms (one queen bed in each) and 1.5 bathrooms. 🍷 Private backyard retreat with a lounge, dining area. 🚗 Private parking located directly behind a secure gate off the back laneway. 📍 steps from Queen East’s best cafes and dining, with easy, immediate access to Lake Shore and the waterfront. In the studio district. Not suitable for small children or pets due to open staircase. Please see picture.

Toronto Skyline view | Walk Everywhere

✨Just bring yourself – everything else is ready!✨ • Private Netflix zone🎬 –Lounge on a cozy daybed and enjoy your favorite shows with a beam projector • Separate dining area – Work, eat, or relax in a dedicated space • Cozy balcony with chairs – Sip your morning coffee or wind down at sunset • Comfy, clean beddings – Get the restful sleep you deserve • Thoughtful amenities provided: Toothbrush/paste, razor, comb, shampoo, conditioner, body wash • Welcome drinks & water – Ready upon arrival 💧

1 BR | Self Check-in | Prime DT | Walk everywhere

Tucked away on the charming and historic St. Patricks Square, this beautiful home offers the perfect blend of peaceful retreat and unbeatable downtown location. Whether you’re visiting Toronto for work, a weekend getaway, or an extended stay, you’ll love coming to this calm, comfortable space right in the heart of the city. You’re minutes from the iconic CN tower, Eaton Centre, Financial District, University of Toronto, TTC subway/streetcars, restaurants, cafes and nightlife and more.

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.

Stylish 1870s Home near Distillery District & Old Toronto

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

Unique Loft in Quiet Pocket | Close to U of T/UHN

Relax and unwind in this unique loft apartment in a rustic house in downtown Toronto! My cat Rikki will be with you also. This space is perfect for anyone looking for a comfy place to stay while exploring what Toronto has to offer. Steps to University of Toronto + Kensington Market. Just north of the entertainment district, 15-min walk to Eaton Centre, 5-min walk to major subway line and University Health Network hospitals. Perfect for couples or single travellers alike!

Yorkville Skyline View 1BR | Standing Desk

🏙️Stay high above Yorkville in a bright one-bedroom condo in the former Four Seasons Hotel building, with skyline views over one of Toronto’s most iconic neighbourhoods. From the bay windows🖼️, you overlook Yorkville’s elegant streets, boutiques, cafés, and evening lights. Just a short walk from the ROM, the 🎓University of Toronto, 🛒Whole Foods, and 🚇Bay/Bloor subway stations, this home offers a refined and comfortable stay in one of Toronto’s most desirable areas.

Steps to Four Seasons Hotel Yorkville Condo

Unobstructed panoramic view in the heart of upscale Yorkville. Minute walk to Bay subway station, Whole Foods, ROM and U of T and high-end restaurants. Easy parking @ 74 Yorkville for $20 (daytime). Around the corner from Toronto's main luxury shopping hub, Yonge + Bloor. *Upscale neighborhood *Highspeed WIFI *Walk score of 96 *Transit score of 93 *Bike score of 98 (rentable Bixi bikes nearby) *Fully equipped kitchen *Full-sized washer/dryer *Gym in building

Yorkville Sinclair

Stay on the 30th floor in the heart of Yorkville in this stylish 430 sq ft one-bedroom suite. Enjoy a full kitchen, in-unit washer & dryer, high-speed WiFi, and optional paid parking. Contactless check-in for a seamless stay. Walk Score 98, Transit 96. Steps to top dining, shopping, and the Royal Ontario Museum. 9 mins to CN Tower & Scotiabank Arena, 27 mins to Pearson Airport. 🎈 Check-in until 8pm, late check-in to 9pm available for a fee.

Prime Downtown Location + 1 Free Parking

Make yourself at home in this professionally maintained condo, thoughtfully designed for guests who appreciate comfort and an exceptional location. Situated in Toronto’s Entertainment District, you'll be just a short walk from the CN Tower, Ripley’s Aquarium, Rogers Centre, and an outstanding selection of restaurants, entertainment, and nightlife. It’s the perfect place to experience everything downtown has to offer.