Holiday rentals with outdoor seating in The Annex, Old Toronto

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in The Annex, Old Toronto

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Guest favourite

Condo in Downtown Toronto

4.98 out of 5 average rating, 240 reviews

Unwind on the Private Terrace of a Downtown Oasis

Soak up the sun or share pre-dinner drinks with friends on the 1,000 square foot terrace and take in 270-degree views of downtown. Hotel-style safes, Missoni cushions and modern artwork add a touch of luxury to this condo. Everything about this space is custom and top of the line. Furnished with high end furniture from Roche Bobois and Jardin De Ville... Missoni pillows… fascinating art...upscale linens from Sferra and Abyss...Stainless steel backsplash in the kitchen… Electric blinds in every room...High Def OLED Smart TV's everywhere and Sonos Sound system for indoor and outdoor listening pleasure. Our 1000 Square Foot terrace is very unique for a downtown location. You have a 270 degree view of the downtown and is a perfect entertainment spot. It's great for sunbathing and some pre-dinner drinks and conversation, or even an intimate catered dinner party. Come have a great time in a safe and secure building with 24 hour concierge and security. Upon arrival, you will generally find fresh flowers, coffee, tea, cream, milk, some juice and beer and a bottle of sparkling wine, plus my favourite Lindt chocolate bar :) Please let me know if you require any additional items prior to your stay and I will do my best to accommodate. There are 3 private bedrooms with queen size hotel style beds. Each of the first two have their own ensuite bathroom + the custom wall to wall cozier 3rd bedroom has a curved OLED High Def TV. There is an available roll-away bed for groups of 7 people, though the 7th person will be in the living area. Each bedroom comes equipped with their own private hotel style safe. There are 3 bathrooms in total. The first has a tub/shower, the second a marble shower and the third is a two piece bathroom. Toiletries are provided. The Kitchen comes fully equipped with all cooking utensils and pots and pans. There is also a Reverse Osmosis water filter with it's own tap at the kitchen sink. If you're a coffee lover, you're really going to enjoy our coffee selection. If needed, parking is in our own private spot off the elevators and is included at no extra charge. Lastly, please note that our spectacular and cozy sister property is right next door with 2 bedrooms and 2 full bathrooms. It sleeps five and also boasts a south view with another 1,000 foot terrace. Together, we can accommodate up to 12 guests. Please let me know if there is anything I can do to make your stay more comfortable. Access of the gym and outdoor space with BBQ is included. (6th floor) Note: If for some reason we cannot meet and greet you upon your arrival, we will send you the lock-box instructions. You can call us at any time for help. The western end of Queen is best known as a centre for Canadian broadcasting, music, fashion, performance, and the visual arts. Chinatown is just a few blocks away for an after-club meal. Famous Queen Street West is just a block away for shopping. Public transit is closeby... streetcars on Queen Street and King Street, plus the Osgoode Subway station is just a short 2 minute walk. Both Union Station (train) and The Bus Terminal are just a 10 minute walk, Billy Bishop (Island Airport) is 10 minute taxi ride away and Pearson Airport can be reached by taxi or by the UP express train from Union Station. Please adhere to the following; No more than 7 sleeping in the suite ...no more than 10 in the suite or on the terrace. There have been numerous noise complaints and management have told us that evictions and $500.00 fines are coming our way for any guests that are loud. We have no say once security gets involved. NO loud music NO parties. NO events without prior written consent. NO smoking indoors (balcony only) Please be respectful of your surroundings and the neighbours. The majority of the people who live in the building are full-time residents who go to work and don't want to have to deal with excessive noise and problems. Please check out the house rules for further important details. Let's all make the AIRBNB experience a positive one!

Guest favourite

Home in Dufferin Grove

4.93 out of 5 average rating, 180 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.

Guest favourite

Guest suite in Little Italy

4.96 out of 5 average rating, 352 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.

Guest favourite

Apartment in Davisville Village

4.9 out of 5 average rating, 262 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

Guest favourite

Home in Downtown Toronto

4.92 out of 5 average rating, 102 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.

Guest favourite

Apartment in Toronto

4.92 out of 5 average rating, 109 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 ✔️

Guest favourite

Home in Downtown Toronto

4.99 out of 5 average rating, 181 reviews

Stylish 1870s Home near Distillery District & Old Toronto

“Rated Top 10 listing by BlogT.0 in Toronto and published frequently as a must stay. Do you appreciate the details? We have you covered here while you unwind at this stylish remodeled circa 1870s Row House. Visit St Lawrence Market, then stroll the pedestrian Distillery District and stop at some great cafes, restaurants or bars. Later, drift off to sleep in the plush, charcoal-hued bedroom under the tiered Restoration Chandelier. This place is perfect for the Toronto experience!

Guest favourite

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.

Guest favourite

Bungalow in Scarborough

4.93 out of 5 average rating, 105 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.

Guest favourite

Home in Little Portugal

4.92 out of 5 average rating, 172 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.

Guest favourite

Apartment in Leslieville

4.96 out of 5 average rating, 125 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.

Guest favourite

Guest suite in East York

4.88 out of 5 average rating, 130 reviews

Chez Chodat - Midtown Leaside near Sunnybrook

This renovated basement suite provides you with a stylish, comfortable living space. Located in historic mid-town Leaside, Chez Chodat offers easy access to Sunnybrook Hospital, the Don Valley trails and a 5 minute walk to popular Bayview & Laird Avenues, offering diverse restaurants and boutique retail stores. Easy access to downtown Toronto by car (15 minutes) or via public transportation. Free street parking.