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 70 holiday rentals in The Annex, Old Toronto
Nightly prices starting at
The Annex, Old Toronto holiday rentals start at $25 SGD per night before taxes and fees
Verified guest reviews
Over 2,210 verified reviews to help you choose
Pet-friendly holiday rentals
Find 10 rentals that welcome pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
70 of The Annex, Old Toronto holiday rentals include wifi 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 North Entrance

Top-rated family-friendly rentals in The Annex, Old Toronto

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite

A modern suite features a spacious bed with a tufted headboard, complemented by light-colored bedding. A glass partition delineates the living area, which includes a round dining table and comfortable seating beneath large windows. A sleek workspace with a printer is also present.

Apartment in Yorkville

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.

FamilyKitchenSleep quality

4.9 out of 5 average rating, 328 reviews

Top guest favourite

The exterior of a tall, modern building is captured from a low angle, highlighting its sleek design and illuminated upper floors. A bronze sculpture of a horse stands prominently in front, set against expansive glass walls reflecting city views.

Flat in Yorkville

Sweet Home 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 Yorkville Village is joyful!

FamilyIndoor spacesCheckout

4.9 out of 5 average rating, 119 reviews

Top guest favourite

A cozy living area features a grey sofa and two matching armchairs, all positioned on a neutral area rug. A modern arc floor lamp provides soft lighting, while framed art adorns the walls. A small glass side table sits beside the sofa, enhancing the space's functionality.

Flat in Midtown

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.

FamilyKitchenBathroom

4.93 out of 5 average rating, 264 reviews

Top guest favourite

A modern two-story cottage is surrounded by lush greenery and trees. The exterior features a combination of natural wood and dark green siding. A covered porch is visible with a personal entrance and outdoor seating. Bicycles are parked nearby, enhancing the outdoor activities available.

Guest suite in Toronto

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.

KitchenIndoor spacesGetting around

4.95 out of 5 average rating, 254 reviews

Guest favourite

A warm and inviting living area features exposed brick walls and a large wooden dining table surrounded by black chairs. Soft lighting from a vintage chandelier casts a gentle glow over a cozy sofa and a stylish entertainment unit, creating a sense of comfort.

Flat in Midtown

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.

KitchenFamilyDecor

4.94 out of 5 average rating, 118 reviews

Top guest favourite

The kitchen features modern cabinetry and stainless steel appliances, including a coffee maker. An island with seating accommodates guests. A dining area with a table is visible, alongside a cozy living space with a blue couch, a decorative painting, and potted greenery.

Home in Midtown

Private 2BR Home Sleeps 6 Near Subway

Welcome to The Laneway Suite! A 1000 sq ft, 2 storey, detached laneway house. Private entrances, Smart Lock, full kitchen with island and all amenities, 1.5 bathrooms, washer/dryer, 2 Queen bedrooms with 32” Smart TV, a living room with a comfy Queen size pull-out couch and 65” Smart TV, a dining room, and a private backyard patio. Whether you’re travelling with your family, your friends, by yourself or on a business trip, this is your perfect getaway! Also suitable for long term stays!

KitchenIndoor spacesLocation

4.99 out of 5 average rating, 103 reviews

Guest favourite

A modern living area features a dark gray convertible sofa and a small dining table near the windows. Natural light enters through two large windows, framed by light curtains. A well-equipped kitchen is visible in the background, showcasing stainless steel appliances and a white countertop.

Flat in Midtown

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.

FamilyIndoor spacesHot tub

4.86 out of 5 average rating, 125 reviews

Top guest favourite

A cozy sleeping area is presented with a spacious bed, featuring soft bedding and decorative pillows. Nightstands flank the bed, providing small plants and ambient lighting. A calming nature print is displayed above the bed, enhancing the serene environment.

Home in Midtown

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.

KitchenIndoor spacesLocation

4.87 out of 5 average rating, 126 reviews

Top guest favourite

A spacious dining area features a large wooden table surrounded by eight dark chairs. Two framed artworks are displayed on the warm yellow wall, contrasted by the light-colored floor and modern furnishings visible in the adjacent living area.

Home in Midtown

Private 3BR Whole Home for Groups Near Subway

A newly built, private 3-bedroom, 3-bath home on a quiet laneway in Toronto’s Annex West, just a 3-minute walk to the subway. Bright, modern, and thoughtfully laid out, this entire home is ideal for families or groups traveling together who want to stay in one shared space. Enjoy a full kitchen, heated floors, unlimited hot water, and fast Wi-Fi. Steps from restaurants, parks, and shops, yet calm and private inside. Best suited for guests with confirmed travel plans.

KitchenFamilyCleanliness

4.99 out of 5 average rating, 125 reviews

Top guest favourite

Guest suite in Midtown

Bright Private Basement Suite | 1BR Near Subway

A newly renovated, private lower-level (basement) 1-bedroom, 1-bath suite located in Toronto’s Annex West, just a 3 minute walk to the subway and buses. Bright, quiet, and thoughtfully designed, this self-contained space is ideal for solo travelers, couples, or short business stays. Enjoy heated floors, unlimited hot water, fast Wi-Fi, a full kitchen, and comfortable living and dining areas—steps from restaurants, parks, shops, and beautiful residential streets.

Indoor spacesKitchenCleanliness

4.98 out of 5 average rating, 223 reviews

Luxe

A modern living room features a gray sofa with decorative cushions, a coffee table, and a cozy rug. Shelves against the wall display books and decorative items, with a warm wooden accent above. A plant and stylish lighting enhance the inviting atmosphere.

Home in Downtown Toronto

The Robert House: Masterpiece in Harbord Village

The Robert House is a beautiful stylish home in the heart of the city. Located just south of the Annex neighbourhood, east of Toronto’s Little Italy and a stone’s throw from Kensington Market and Chinatown. Enjoy this remarkable home - steps to subway, landmarks, parks, markets, cafes, restaurants, bars & shops. You will remember your stay in this bright & spacious 3+1 bed, 2.5 bath with soaring 10 foot ceilings and high-end finishings.

FamilyIndoor spacesLaundry

4.93 out of 5 average rating, 136 reviews

Top guest favourite

A dining area is presented with a wooden table set for meals. A textured vase holds an arrangement of greenery and foliage. Black-framed photographs adorn the wall, creating an artistic backdrop, while a pendant light offers soft illumination.

Flat in Midtown

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

Indoor spacesKitchenCheckout

4.97 out of 5 average rating, 115 reviews