
Family-friendly holiday rentals in The Annex, Old Toronto
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in The Annex, Old Toronto

Total holiday rentals
Explore 80 holiday rentals in The Annex, Old Toronto

Nightly prices starting at
The Annex, Old Toronto holiday rentals start at $34 NZD per night before taxes and fees

Verified guest reviews
Over 2,090 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 of The Annex, Old Toronto holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across The Annex, Old Toronto rentals

4.8 Average rating
The Annex, Old Toronto stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
The Annex, Old Toronto's top spots, include Royal Ontario Museum, Bata Shoe Museum, and Spadina Station
Top-rated family-friendly rentals in The Annex, Old Toronto
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Luxury Yorkville Escape | Condo in Prime Location
Discover refined living in this beautifully furnished apartment in Yorkville Toronto’s most glamorous & exclusive neighborhood. With new furniture & modern appliances, this space blends comfort with sophistication. Step outside and find yourself surrounded by luxury boutiques, acclaimed restaurants, chic cafes, & world-class art galleries. With Bay subway station just a 3 minute walk away, the entire city is at your fingertips. Elevate your lifestyle in a place where elegance meets convenience.

Beautiful Petit Gem Ap. In Downtown! Walk Anywhere
Welcome to our lovely petit aparment in heart of downtown Toronto! Our place has everything you might need in order to enjoy the city, work remotely and have a great time when the weather outside is not the best! Located right in downtown, you can basically walk anywere fast: Eaton Centre, Dundas Square, U Toronta, etc. Enjoy many of the high end stores located in the area and also some of the best restaurants! The entire place is sensitized using UV lights and COVID 19 cleaning solutions.

Cozy small newly built Toronto Islands getaway
Escape to a modern cottage on Toronto Island Looking onto Lake Ontario is our newly constructed modern home. Enjoy our cozy private guest suite in our family home with a kitchenette, ensuite bathroom, and private entrance Just a quick ferry ride from the bustling downtown core come explore the Toronto Islands which is the biggest car-free community in North America; with beaches, trails & skyline views as well as an amusement park in the summer. We also have 2 bikes you can use to explore.

Cute Private Apartment near University of Toronto
This cozy main floor apartment with private walk out patio, located on a quiet street in the beautiful Annex neighbourhood. Free parking Laundry in building Shared backyard 5 minute walk to subway (Christie Station) 5 minute walk to Bloor Street, the restaurants and bars of Korea Town, and historic Christie Pits Park. Walking distance to University of Toronto and George Brown College Casa Loma campus. There are a lot of great restaurants, bars and local grocery stores within a short walk.

Luxurious Annex/Yorkville 1300 Sq Ft & Parking
Beautifully appointed, top quality furnishings & amenities , spacious Yorkville/Annex rental. Full 1300 sq foot. apartment located within a Heritage Victorian Brownstone! Exceptionally located, walking distance to subway, restaurants and all the sights! Walk to Casa Loma, Royal Ontario Museum & Yorkville. Parking, Wifi, Chromcast, Fibe TV, Local High Def TV included. Fully equipped gourmet kitchen. Air Conditioned. Digital safe for valuables. Treat yourself to pantry snacks, coffee & tea.

Cozy 1 Bedroom Unit in the Annex, Free Parking
Welcome! This cozy unit is a great place to stay if you want to be in the city without feeling like you're in a concrete jungle. Located in the Annex, it's a food haven for those that are interested in exploring different places to eat. It's also a 5 min walk away from the Bloor/Spadina subway station (or Bathurst station in the other direction), so it's great for commuting around to different areas of Toronto. Yorkville, the ROM, and Casa Loma are also under 10 mins drive from here.

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.

Annex Haven: 1 Bedroom plus Den
This centrally located private space is newly updated with new flooring, furniture, and bathroom. It includes a separate entrance with its own kitchen and laundry. Very quiet residential neighbourhood with old growth trees. Walking distance to Christie subway station or Dupont subway station. Be downtown within 20 minutes. Close to Koreatown and many great restaurants on Bloor Street. 5 min walk to 4 grocery stores and LCBO. Basement space not suitable for people over 6 feet tall.

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

Renovated Modern 2 Bedroom Suite w/ City Views
Experience the city like a local in this newly renovated two-bedroom suite. This ample, bright, airy space has beautiful city line views. We are centrally located (steps away from Casa Loma and downtown) with plenty of options for food, drinks, and local shops. The area has excellent walkability and great transit access. 24km from/to Pearson Airport and 6km from/to Billy Bishop Airport

Contemporary cozy home in the Annex
This 2 bed/2bath home is located in the more northern part of the downtown core called West Annex/Seaton Village and is on a cul de sac. Steps from TTC, Yorkville, art galleries, restos & more. The small urban-chic, clean and bright home boasts two balconies off either bed & a spacious backyard off kitchen. Permit No: STR-2010-GZSXPH Application Reference No: 3383-645

Bright, Stunning Victorian Townhouse in the Annex
Newly renovated, 3 level, 2-bedroom sun-filled unit, situated in the Annex. Brick fireplace, central air conditioning and heating, wooden floors and exposed brick. Steps away from Bloor St, coffee shops, restaurants, shops, galleries, parks and much much more. Short walk to Bathurst and Spadina Subway, Casa Loma, Yorkville, University of Toronto, and museums.
Popular amenities for The Annex, Old Toronto family-friendly rentals
Family-friendly home rentals with a hot tub

Backyard Oasis | Hot Tub & Playground

The Penty: Luxurious Penthouse with Pool, Hot Tub

FIFA: 4BR: 365 Days Open- Heated Pool & Hot Tub

**30%OFF** Lake view property ❤️ of downtown

Modern Downtown Loft with Private Garden

FIFA fan zone Pool/HottubFree parking walk to BMO

1 Bedroom + Den (Office/Bidet/Balcony) near Rogers

Stylish Downtown Toronto Condo + Free Parking
Family- and pet-friendly home rentals

Sun-Filled Two-Storey Loft | 15 Minute FIFA Walk!

Toronto Island Wonderland View

Comfy Oasis In Historic Downtown Neighborhood

Spacious Mid Century w/Patio

Stunning Yorkville Townhome Backing onto Park
Garden Home @ Trinity Bellwoods Park

Authentic Hard Loft in the Heart of Toronto

Kimchi Loft in Korea Town
Family-friendly home rentals with a pool

Lux amenities/fast WIFI/walking to sub Yorkville

Stunning Skyline View Condo, Steps to CN Tower

The Farmer's Cottage

King West Triplex Main FLR PVT APT 1 BDRM Parking

Beautiful Yorkville Luxury Condo

Charming Condo w Parking, CN Tower View & Pool

2BR Across from CN Tower & MTCC

Stylish 1+1 Corner Suite |Steps to Lake&Downtown
Destinations to explore
- Fitness-friendly rentals The Annex
- House rentals The Annex
- Apartment rentals The Annex
- Rentals with a washing machine and dryer The Annex
- Pet-friendly rentals The Annex
- Rentals with outdoor seating The Annex
- Rentals with a fireplace The Annex
- Rentals with a patio The Annex
- Family-friendly rentals Toronto
- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Enercare Centre
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Harbourfront Centre
- Nike Square One Shopping Centre
- Toronto Eaton Centre
- Niagara Falls State Park
- Downsview Park
- Exhibition Place
- Toronto Zoo
- Trinity Bellwoods Park
- Niagara Falls
- Casa Loma
- Massey Hall
- Scarborough Town Center
- York University
- Casino Niagara
- Fallsview Indoor Waterpark
- Dufferin Grove Park





