Holiday rentals with outdoor seating in The Annex, Old Toronto

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Top-rated rentals with outdoor seating in The Annex, Old Toronto

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Top guest favourite
A charming coach house is framed by lush greenery and flowering plants. A stone pathway leads to the entrance, flanked by potted plants. Outdoor seating areas feature vibrant blue fabrics, and a grill is positioned on the left, offering a welcoming outdoor space.
Guest house in Scarborough
4.96 out of 5 average rating, 130 reviews

Private Coach House near the Bluffs

This separate, minimalist, self-contained coach house is a perfect quiet escape for one, and can also intimately accommodate two persons. Wake up in natural light with all the essential home comforts: premium queen-size mattress, hypoallergenic, 100% cotton linens, a private bathroom, toiletries and meal preparation basics. No kitchen. Nearby options for prepared meals, groceries + delivery. No TV. No housekeeping fees. A 20-minute getaway from the downtown core near the lake in the east end.

Top guest favourite
A modern living area features a spacious, cozy sectional sofa with decorative pillows. A large window offers views of the city skyline and access to a balcony adorned with patio furniture. Natural light fills the room, complementing the contemporary decor and wooden flooring.
Apartment in Liberty Village
4.98 out of 5 average rating, 122 reviews

Central condo in heart of Liberty Village +parking

Right on the park! Enjoy a comfortable & convenient stay in the heart of one the most vibrant neighborhoods in Toronto! ALL amenities within walking distance; Shops, bars, patios, groceries, parks, trails, restaurants, concerts, transit, nightlife (King st and Queen St) all just steps away. Short walk to the Waterfront/Lake Ontario, Coca-Cola Coliseum, Bud Stage, BMO field, Fort York, Bentway, CNE, & more! This location is PERFECT for quick & easy access to any experience the city has to offer!

Top guest favourite
The living room is furnished with a modern gray sofa adorned with accent pillows. A coffee table, featuring a stack of magazines and decorative items, sits on a textured area rug. A television is mounted above a blue cabinet against a light gray wall, with framed art and a plant nearby.
Guest suite in Trinity-Bellwoods
4.96 out of 5 average rating, 416 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 on foot, plus close transit with a stop right at your doorstep.

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 Centre Island
4.94 out of 5 average rating, 213 reviews

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.

Guest favourite
Guest house in Little Portugal
4.86 out of 5 average rating, 484 reviews

Unique Studio with Sauna

Perfect sanctuary for two with 11' high cedar-ceilinged right in the heart of Toronto. ♡ Architectural designed space with Private Sauna ♡ Outdoor Patio with Firepit ♡ Hotel Inspired Space with Super Fast WIFI ♡ Automated Check in & Check Out ♡ Street Parking ♡ 100/100 Walk Score ♡ 100/100 Transit Score ♡ Walking distance to Queen West ♡ Flexible Check in Check out - Message for Details 4K Netflix ♡ A/C ♡ Coffee Bar ♡ Record Player ❤ Book today! Please note: NO KITCHEN OR LAUNDRY

Top guest favourite
A modern living area features a dark sofa and a light blue chair, positioned around a glass-top coffee table. A large wall-mounted TV is displayed, while decorative lanterns adorn a white console table with wicker baskets. Natural light streams through a window beside a potted plant.
Flat in Little Portugal
4.9 out of 5 average rating, 128 reviews

Cozy Private Apt DT Toronto + Free Parking

Step into this bright, cozy 1BR 1BA private suite in Toronto’s West End—minutes to great cafés, restaurants, shops, and easy transit to downtown. Ideal for couples, friends, or business travelers who want comfort and convenience. ✔ Queen Bedroom + Sofa Bed (Sleeps 4) ✔ Full Kitchen + Dining ✔ Workspace ✔ Smart TV + Streaming ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Shared Backyard ✔ Self Check-In Enjoy Toronto like a local! Coming for the 2026 World Cup? BMO Field is ~7 mins by car/taxi!

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 Annex
4.87 out of 5 average rating, 100 reviews

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.

Top guest favourite
A sunset over the water is portrayed, with a golden sun reflecting on the calm surface. The horizon features a silhouette of trees, creating a serene atmosphere. Soft waves ripple gently in the foreground, enhancing the tranquil setting.
Flat in Centre Island
4.95 out of 5 average rating, 110 reviews

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.

Top guest favourite
Home in Corktown
4.99 out of 5 average rating, 242 reviews

Stylish 1870s Home near Distillery District & Old Toronto

Named a Top 1% by Airbnb, former Plus listing & top 10 Toronto stay by BlogTO, this beautifully restored 1870s rowhouse blends historic charm with modern refinement. Thoughtfully designed throughout, it’s located downtown steps from St. Lawrence Market, the Distillery District, 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

Top guest favourite
Guest suite in Annex
4.98 out of 5 average rating, 190 reviews

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.

Superhost
A tropical balcony area features two stylish chairs beside a decorative wall adorned with greenery. Vibrant cushions add color, while potted plants enhance the calming atmosphere. A textured rug lies beneath, complementing the space, which offers a view of the city through large glass doors.
Apartment in Harbourfront
4.87 out of 5 average rating, 113 reviews

Downtown Condo w/ tropical balcony beside CN Tower

Enjoy this luxury condo in the heart of downtown Toronto with city views! Located right in the entertainment district next to Scotiabank Arena, Roger's Centre, CN tower, Harbourfront and so much more! It's a relaxing sweet escape while being in all the action! The condo building is also attached to the Underground Path so you can access many areas of Downtown Core without stepping outside!

Top guest favourite
The living space features a modern sofa accompanied by a vibrant area rug. A small dining table with four chairs is positioned near large windows that allow natural light. Wall art and a stylish light fixture enhance the contemporary design.
Home in Trinity-Bellwoods
4.92 out of 5 average rating, 372 reviews

Garden Home @ Trinity Bellwoods Park

Stay in the amazing Trinity Bellwoods area in my modern 2 bed/1 bath apartment with a tree covered deck for coffee in the mornings! All mod cons. Cable/Netflix. Check In 3PM-Out 11AM. Parking can be organized for city streets by me. NOTE: stairs are narrow to the lower level, where the bathroom, laundry & 2nd bedroom are located. This bedroom has a 6 ft-2in ceiling height.

Popular amenities for outdoor seating rentals in The Annex, Old Toronto

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Quick stats about holiday rentals with outdoor seating in The Annex, Old Toronto

  • Total holiday rentals

    Explore 40 holiday rentals in The Annex, Old Toronto

  • Nightly prices starting at

    The Annex, Old Toronto holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 1,760 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 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

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