Pet-friendly holiday rentals in The Annex, Old Toronto

Toronto Island Wonderland View

Toronto Islands are a 10 minute ferry ride away from downtown Toronto. Switch from the hustle and bustle of the city to the tranquillity of one of Toronto's most coveted parks. Unique to any other metropolitan city, Toronto Island has limited vehicle access. This car free area boasts 6 kilometres of nature walks, children and pet friendly access to beaches, Centre island amusement park, artist exhibitions, restaurants and even a nude beach. A perfect getway for the hybrid vacationer.

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.

Admire City Views from Bed at this Chic Apartment

The critics have spoken! This five-star rated, professionally designed unit offers a fresh, functional, and beautifully curated living experience. Every piece of artwork and each accessory has been thoughtfully selected to enhance comfort, style, and positive energy throughout the space. This spacious one-bedroom, one-bathroom suite features a fully equipped kitchen, open living and dining areas, and a versatile den — perfect for working remotely or relaxing after a day in the city.

Yorkville 29th Floor Celebrity Suite GREAT VIEW

This top floor Yorkville celebrity suite corner suite has unobstructed views of Yorkville from the Queen sized bed in the master bedroom. Steps to UofT campus, and less than 5mins walk from 3 subway stops. Luxury shopping and stores like Whole Foods, Louis Vuitton, Holt Renfrew, Nespresso, Dolce+Gabbana, Tiffany at your front door. Perfect for business or leisure. The building has a gym on the 3rd floor. The suite sleeps up to 4 people in 2 areas. The sofa bed in the living room.

Spacious Mid Century w/Patio

Adorable Historic Home with Private Patio & BBQ. ♡ 3 bedroom & 1.5 bath (1 King & 2 Queens) ♡ Hotel Inspired Home with Super Fast WIFI ♡ Automated Check in & Check Out ♡ Steps from St. Clair transit line / connects to Subway ♡ 90/100 Walk Score ♡ 100/100 Transit Score ♡ Walking distance to Casa Loma | Rated #1 by BlogTO of Places to Visit in Toronto ♡ Flexible Check in Check out - Message for Details ♡ A/C ♡ Laundry ♡ BBQ & Fully Equipped Kitchen ❤ Book today!

Backyard Oasis | Hot Tub & Playground | Near DT

Summer in Toronto starts here — a private fenced backyard with an all-season 6-person hot tub, fire pit, BBQ, and a playground the kids won't want to leave. Four bedrooms, three full bathrooms, sleeps 9 comfortably — 15–20 minutes from downtown. Need more space? Add the basement unit for up to 15 guests total. ★ "The backyard is AMAZING!!! The house is super close to the parade and it's walking distance to so many restaurants and shops." — Devon, Caribana 2025

Downtown Gem! Free Park + Roof Deck + Backyard BBQ

Prime location with a 99 Walk Score, 98 Transit Score & 99 Bike Score—steps from restaurants, shops, and transit, yet tucked on a quiet street for peaceful sleep 😴 Sparkling clean with comfy beds, in-home laundry, and flexible early check-in/late check-out when available. Dedicated quiet work/study space for 4. Enjoy free garage pad parking, rooftop deck, gas BBQ, treed backyard, and complimentary coffee/tea. Comfort, convenience, and thoughtful touches await!

Beautiful, Bright 1-Bedroom in Victorian Home!

Feel at home in the heart of Toronto in this beautifully renovated century old Victorian main-floor suite on a quiet Kensington Market street. Enjoy an incredible bright solarium, spacious living room, fully equipped galley kitchen, and large bedroom with a king size bed. Private furnished backyard to enjoy. Walk to Kensington Market, Chinatown, Little Italy, U of T, and major hospitals. A stylish, comfortable home base perfect for exploring the city.

Luxury 4BR | World Cup | High Park & Beach

Luxury 4-bed, 4.5-bath home sleeping 8 in Toronto's vibrant west end. Steps from the cafes and restaurants of Roncesvalles Village, 10-min walk to Sunnyside Beach and High Park — Toronto's largest public park. BMO Field (World Cup 2026 venue) is a 30-min walk or quick rideshare away. Glimpses of Lake Ontario from the master terrace. Self check-in, high-end finishes throughout, fast WiFi, dedicated workspace, and pets welcome.

Stunning Yorkville Townhome Backing onto Park

Situated in the heart of Yorkville, this 3 bedroom 2.5 bathroom townhouse with views overlooking Ramsden Park, is the ideal oasis for families, couples, or people travelling for work. The space features a bright sun-filled interior featuring a gas fireplace, WIFI, Smart TV with all apps and fully equipped kitchen. The home backs onto green space with a wonderful back deck and eating area.

Panoramic Views in Bright Loft + Free Parking

The loft has more windows than it has walls and offers a clear view of the city sky. Located in the heart of downtown, you're close to all major attractions, restaurants, bars, and coffee shops. Toronto's legendary Fashion District is where you'll find all the action. Waterworks Food Hall is right next door and makes a great co-working location. Strictly, no parties allowed.

Garden Home @ Trinity Bellwoods Park

Enjoy the amazing Trinity Bellwoods area/park & Ossington in my modern 1 bed/1 bath apt; with a fold down double bed in the living room, for extra guests. Start the AM on the deck with your coffee. Cable/Netflix. Check-In 3 PM, Check-Out 11 AM. Parking permits can be organized. Lower level- bathroom, storage & laundry. App. Ref.#2804-346