The Annex holiday rentals
We found 252 holiday rentals — enter your dates for availability
Discover a selection of 8 homes and other holiday rentals in The Annex that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and garden. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.
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Find the best place to stay - The Annex

Downtown Toronto: Cozy Retreat in the Annex
Sleeps 5 · 3 bedrooms · 2 bathrooms

Luxury 2bed3bath Condo in Yorkville | Gym |Parking
Sleeps 4 · 2 bedrooms · 2+ bathrooms

Teahouse Condos in Downtown Toronto
Sleeps 2 · 1 bedroom

The Britt Condos in Downtown Toronto
Sleeps 4 · 1 bedroom

Modern St. Clair West Suite w Private Patio & BBQ
Sleeps 4 · 2 bedrooms · 1 bathroom

Stylish 3BR Urban Retreat, near Christie sleeps 6
Sleeps 6 · 3 bedrooms · 1 bathroom
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental in The Annex?
In The Annex, apartments are the most popular type of holiday rental, with around 12 available in this vibrant neighbourhood. These apartments are typically situated close to local cafes, bookstores, and parks, offering a lively option. Guests can expect amenities such as fully equipped kitchens, comfortable living spaces, and some may even feature private balconies for enjoying the city views. The area is well-connected to public transport, making it easy for visitors to explore nearby attractions.
What are popular rental amenities in The Annex?
In The Annex, popular rental amenities include fully equipped kitchens, ideal for those who prefer cooking their own meals. Many rentals also feature coffee and tea makers, ensuring guests can enjoy a warm beverage at any time. For travellers bringing furry friends, several properties permit pets, along with provisions for service animals. Additionally, air conditioning is commonly available, providing comfort during warmer months.
Can I find family house rentals in The Annex?
In The Annex, Ontario, there are several family-friendly house rentals available. This vibrant neighbourhood is known for its tree-lined streets and proximity to various attractions. Many properties in the area feature spacious living rooms, fully equipped kitchens, and outdoor spaces where children can enjoy themselves. Some homes may also come with additional amenities like game rooms or patios for family gatherings.Visitors will appreciate being close to cultural highlights such as the Royal Ontario Museum and the lush greenery of Queen's Park, great for leisurely strolls or picnics. The local dining scene offers diverse options, making it easy for families to find suitable meals after a busy day of exploring.
Can I rent a holiday home with a pool or hot tub in The Annex?
In The Annex, Ontario, there are several holiday homes available for rent that feature pools and hot tubs, making it an attractive option for travellers seeking relaxation. This vibrant neighbourhood, known for its historic architecture and proximity to the University of Toronto, offers a mix of cultural attractions, parks, and dining experiences.Rentals in The Annex typically come with a variety of amenities. Many properties boast private pools and hot tubs, alongside spacious outdoor areas for sunbathing or entertaining. Inside, guests can expect fully equipped kitchens, comfortable living spaces, and modern conveniences such as Wi-Fi and air conditioning. This combination of amenities ensures a comfortable and enjoyable stay, whether for a family getaway or a trip with friends.
Can I book pet-friendly holiday rentals in The Annex?
In The Annex, travellers can indeed find several pet-friendly holiday rentals, making it a great choice for those wanting to bring their furry companions along. This vibrant neighbourhood is known for its vibrant mix of restaurants, cafes, and shops, all within easy walking distance from many rental properties.The holiday rentals in this area often feature modern amenities including fully equipped kitchens, spacious living areas, and outdoor spaces such as balconies or patios, which can be great for enjoying the fresh air with pets. Additionally, The Annex is close to various parks, offering ample opportunities for pet walking and playtime. The nearby Christie Pits Park, for instance, has open green spaces and walking trails, ensuring that both you and your pet can enjoy the outdoors.
When is the best time to visit The Annex for a holiday rental?
The most popular time to visit The Annex is during the peak season, which runs from May to July. This vibrant period draws visitors eager to immerse themselves in the lively option, with plenty of outdoor activities and cultural events to enjoy. The warm summer months provide a fantastic backdrop for exploring the area's unique neighbourhoods, parks, and local attractions, all while basking in temperatures that typically range from 15 to 25 degrees Celsius.July is particularly bustling, as the city comes alive with festivals, open-air markets, and an array of outdoor dining options. If you're drawn to a dynamic environment and wish to soak in the local culture alongside fellow travellers, this is an ideal time for your holiday rental in The Annex.For those seeking a more budget-friendly experience, consider planning your visit in December. While the weather can be chillier, with temperatures averaging around 0 degrees Celsius, this month offers a quieter charm. You can enjoy the festive decorations and holiday events without the crowds, and it's a wonderful time to experience the warmth of local hospitality.Ultimately, the best time to book your stay in The Annex hinges on your preferences.
Are there any remote work holiday rentals in The Annex?
In The Annex, Ontario, there are around 12 remote work-friendly holiday rentals available for those looking to combine work and leisure. This vibrant neighbourhood, known for its lively mix of shops, cafes, and cultural attractions, offers a great environment for remote workers. Many of the properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces, and comfortable living areas, making it easy to stay productive while enjoying the local lifestyle.With its proximity to points of interest like the Royal Ontario Museum and the beautiful parks of the area, these rentals are ideal for those who want to explore during their downtime. Additionally, the local coffee shops and restaurants provide excellent spots for informal meetings or breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are the top attractions in The Annex, Ontario, Canada?
The Annex in Ontario is a vibrant neighbourhood known for its cultural richness and proximity to various attractions. Visitors can explore the Royal Ontario Museum, which showcases an impressive collection of art, culture, and natural history, making it a must-visit for those interested in learning more about both local and global heritage. Another highlight is the scenic Philosopher's Walk, a lovely pathway that connects the museum to the University of Toronto, providing a peaceful escape amidst the urban setting.The area is also well-known for its lively mix of shops, cafes, and restaurants along Bloor Street, offering a diverse culinary scene and a variety of boutiques. For those who enjoy green spaces, the nearby Queen's Park is great for leisurely strolls or picnics. Additionally, the neighbourhood's proximity to Yorkville allows easy access to high-end shopping and art galleries, further enriching the experience for visitors.
Are all fees included in the The Annex holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any The Annex holiday homes with parking?
Stayz offers a wide selection of holiday homes in The Annex with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for The Annex holiday homes?
You can find great discounts on holiday homes in The Annex on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my The Annex holiday home booking on Stayz?
To find The Annex holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in The Annex?
A long-stay holiday home in The Annex is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a The Annex holiday home?
Book your The Annex holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in The Annex?
Prices for holiday homes in The Annex vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in The Annex to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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