Vacation rentals with outdoor seating in The Annex, Old Toronto

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

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Guest favorite

Home in Dufferin Grove

4.93 out of 5 average rating, 179 reviews

Classic 1 Bedroom Suite

Toronto Short-Term Rental Registration Number: STR-2009-GBSXPD *No Parties* Situated on the main floor of a 3600-square foot Victorian home built in 1908, this guest space is recently renovated with modern amenities. Located on the border of Little Italy and Dufferin Grove it is conveniently only a 10-minute walk to the Ossington subway station and a 2-minute walk to College st. With restaurants, parks, coffee shops, bars, grocery stores, a mall and a movie theatre all within 20 minutes on foot.

Dec 14 – 21

R3,284 ZAR per night

Guest favorite

Guest suite in Little Italy

4.96 out of 5 average rating, 351 reviews

Ossington Rowhouse + Private Garden

Enjoy a fully private retreat in a gorgeous guest suite! Relax with a glass of wine in your own backyard garden at this romantic urban cottage—a 700 sq ft suite on two floors of a designer's 4 level home. 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 enjoy some of the city's best bars and restaurants just steps from home, and explore the city easily—there's a transit stop right outside the door.

Jul 30 – Aug 6

R3,531 ZAR per night

Guest favorite

Apartment in Davisville Village

4.9 out of 5 average rating, 260 reviews

Mid-town T.O. getaway - conveniently located

Bright and spacious. Ideal for singles or couples. Very safe family-oriented neighbourhood, close to public transit (TTC), restaurants, theatres, Sunnybrook Hospital for medical staff or patient visitors. Queen-size bed, couch, TV (with Netflix, AppleTV, Prime Video, no cable), private full kitchen and bathroom. All towels and linens provided. Shared laundry machine 12 min walk to Yonge St. and Subway, 2 min walk to bus stop (6 mins to Yonge by bus), 25 mins from downtown via public transit

Jul 29 – Aug 5

R2,137 ZAR per night

Guest favorite

Home in Downtown Toronto

4.92 out of 5 average rating, 101 reviews

Heritage House all to Yourself! 1BR 3BA 2 Liv Rms

Beautiful detached heritage home in downtown Toronto. Wellesley Subway half block away. Just 1 bedroom w/ensuite. Formal dining room, living room, kitchen w/breakfast room, separate TV room, sun room. NO SMOKING OR VAPING OF ANY KIND Indoors AND Back Patio. (violation = immediate eviction and max. AIRBNB fine .) NO PARTIES: caretaker lives nearby and will evict. **PLEASE NOTE: Oven is a counter-top convection oven that bakes and broils **PLEASE NOTE our cleaner comes every Monday morning.

Apr 5 – 12

R3,859 ZAR per night

Guest favorite

Apartment in Midtown

4.93 out of 5 average rating, 76 reviews

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.

Jul 17 – 24

R2,778 ZAR per night

Guest favorite

Apartment in Toronto

4.92 out of 5 average rating, 107 reviews

Spacious & Vibrant upstairs apartment

There are several shops and restaurants on St. Clair Ave W. Plenty of transit options north of you on the St. Clair line or the bus line on Dufferin. A dog within minutes from the home. The actual space is perfect. Opposite of the open concept apartment, this spacious one bedroom had a separate eat-in kitchen, separate living room, and bedroom. The apartment has the fastest wifi speed. The second floor back terrace has a lovely view with gorgeous sunsets. Not a shared space. Parking ✔️

Aug 11 – 18

R2,794 ZAR per night

Guest favorite

Tiny home in Downtown Toronto

4.91 out of 5 average rating, 132 reviews

Cozy tiny house in Trinity Bellwoods, Toronto

Our place is close to Trinity Bellwoods Park—in one of the liveliest neighbourhoods in Toronto. The tiny house is a 400sf loft studio with a lovely private garden. Private entrance can be accessed through laneway. A two-sided fireplace adds great ambiance. Stylish, compact, and right in the middle of Toronto's trendiest area. Not recommended for little kids as the loft is quite high and is accessed via a ladder but excellent for couples, solo adventurers, and business travelers.

Jan 18 – 25

R2,519 ZAR per night

Guest favorite

Bungalow in Scarborough

4.93 out of 5 average rating, 103 reviews

Stylish Apartment! Steam sauna! Free Parking!

Check into this spacious and professionally decorated luxury apartment! You'll find comfort at every step with heated floors, a double steam sauna shower, fully stocked kitchen and 55" HD TV cable and Netflix. Lightning fast Bell internet (8gig) for streaming and work. Free Parking. 6 mins walk to the subway (Victoria Park). 15-20 mins by subway OR driving to the downtown core of Yonge and Bloor. 10mins drive to Scarborough Bluffer’s Park Beach and 7mins Drive to Woodbine Beach.

Aug 27 – Sep 3

R2,279 ZAR per night

Guest favorite

Loft in Downtown Toronto

4.92 out of 5 average rating, 48 reviews

Bright and Warm, Luxury Annex Loft

Welcome to our beautifully renovated 2-story loft located in the historic Annex neighborhood of Toronto. Our cozy and comfortable living space is filled with natural sunlight throughout the day. On the main floor, you'll find a modern kitchen and dining area, with a spiral staircase leading up to the second floor bedroom, washroom, and deck with stunning views of the Toronto skyline. Explore the charming Annex neighborhood or use the Spadina subway station to explore the city.

Dec 2 – 9

R3,001 ZAR per night

Guest favorite

Home in Little Portugal

4.92 out of 5 average rating, 171 reviews

Charming coach house / guest house downtown

Private and secluded, completely separated, fully serviced and renovated guest house / urban cottage with a beautiful private patio nestled among the mature trees of Dufferin Grove - one of Toronto's most vibrant and interesting neighbourhoods. Find quiet, peace and tranquility in a private oasis, tucked away behind trees and the residential streets, located in the middle of Toronto's trendiest urban centres: Little Italy, Dundas West, Ossington, Little Portugal and Queen West.

Oct 28 – Nov 4

R2,514 ZAR per night

Guest favorite

Home in Niagara

4.91 out of 5 average rating, 265 reviews

King West Victorian Studio Gem

Victorian Century Home Quiet Residential Street in the Heart of Downtown Toronto Overlooks Park + Outdoor Public Pool Open Concept 735 sq ft Sunny, Exposed Brick, Chandeliers Hardwood Floors Throughout Soaring 11' Ceilings Fully Equipped Eat-in Kitchen Private Laundry Private Backyard/Garden Business Traveler Ready Steps to King Streetcar Minutes to Queen & King West Nightlife, Shops, Cafes + Restaurants & King West Theatre District Street Permit Parking

Aug 2 – 9

R3,137 ZAR per night

Guest favorite

Apartment in Leslieville

4.96 out of 5 average rating, 124 reviews

Modern Private Lower Level Apartment Leslieville

Self-contained 1 bedroom lower level apartment with private entrance. The double bed sleeps 2 same with pull out couch. The apartment has a full kitchen with an induction cooktop, wall oven, dishwasher, microwave, fridge, toaster, kettle, and coffee maker. The unit is 550 sq feet. TV & WiFi. There is private parking available at $10.00 per night. This must be arranged at the time of booking to guarantee it is available. See below for full details.

Aug 28 – Sep 4

R2,227 ZAR per night