Leaside holiday rentals
We found 32 holiday rentals — enter your dates for availability
Discover a selection of 9 homes and other holiday rentals in Leaside that are perfect for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, including air conditioning and Wi-Fi. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
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Find the best place to stay - Leaside

Quiet Luxury Stay at Prime Location • 2-Min Walk to Leaside Subway• Pet Friendly
Sleeps 6 · 4 bedrooms · 2 bathrooms

High End 3BR Retreat in Leaside with Parking
Sleeps 7 · 3 bedrooms · 2+ bathrooms

Lovely Family Home in Leaside
Sleeps 8 · 4 bedrooms · 2+ bathrooms

Stylish 2bed2bath| Parking | Gym | Sauna|4ppl
Sleeps 4 · 2 bedrooms · 2 bathrooms

Leaside/Sunnybrook Terrace Executive 2 Bedroom, 3 Bathroom, Terrace, Condo
Sleeps 4 · 2 bedrooms · 2+ bathrooms

Bright Luxury 2BR Condo w/ Parking | Nature Trails, Cafés & Transit Steps Away
Sleeps 4 · 2 bedrooms · 2 bathrooms
- 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 Leaside?
In Leaside, holiday houses are the predominant type of holiday rental, with about 18 available in this charming neighbourhood. These properties typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable home away from home. Additionally, there are several apartments available, which provide a more compact living option while still offering essential amenities such as kitchen facilities and cosy living areas.
What are popular rental amenities in Leaside?
In Leaside, popular holiday rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, alongside dedicated workspaces featuring desks and desk chairs for those needing to attend to business matters during their stay. Many rentals also provide coffee and tea makers for a warm beverage at any time, as well as decks or patios where guests can relax outdoors.
Can I find family house rentals in Leaside?
In Leaside, Ontario, there are several family-friendly house rentals available, making it a great choice for groups looking to enjoy the area. These homes typically feature spacious layouts, ideal for family gatherings, along with amenities such as fully equipped kitchens for preparing meals together and comfortable living rooms for relaxation.Visitors will appreciate the proximity to local parks, such as Leaside Memorial Community Gardens, where children can play and families can enjoy picnics. The neighbourhood also boasts easy access to charming shops and eateries along Bayview Avenue, ensuring that everything needed for a pleasant stay is within reach.
Can I rent a holiday home with a pool or hot tub in Leaside?
In Leaside, Ontario, there are several holiday homes available for rent that feature both pools and hot tubs, making it an attractive option for travellers seeking relaxation. This charming neighbourhood is known for its family-friendly atmosphere and well-maintained parks, providing a pleasant environment for visitors.Rentals in Leaside often come equipped with private pools, hot tubs, and spacious outdoor areas, great for enjoying warm summer days or unwinding in the evenings. Inside, many properties offer modern amenities such as fully equipped kitchens, comfortable living spaces, and Wi-Fi, ensuring a convenient stay.The local area is also well-connected, making it easy to explore nearby attractions, shops, and dining options.
Can I book pet-friendly holiday rentals in Leaside?
In Leaside, Ontario, there are several pet-friendly holiday rentals available, making it a great option for travellers looking to bring their furry companions along. The area is known for its charming residential atmosphere, with holiday properties often featuring amenities such as spacious living areas, well-equipped kitchens, and outdoor spaces, which are great for both relaxation and entertaining.Leaside is conveniently located near parks and green spaces, providing ample opportunities for walks and outdoor activities with pets. The nearby Leaside Memorial Community Gardens offers beautiful trails and open areas where pets are welcome, ensuring that both you and your pet can enjoy the outdoors together. Additionally, the local cafes and shops often have pet-friendly policies, adding to the overall charm of the neighbourhood for animal lovers.
When is the best time to visit Leaside for a holiday rental?
The best time to visit Leaside for a holiday rental is during the summer months, particularly in July. This peak season, running from July to September, offers vibrant opportunities for outdoor activities, community events, and festivals. The warm weather, typically around 20 to 30 degrees Celsius, provides a comfortable atmosphere for exploring local parks, enjoying picnics, and participating in various recreational activities.July stands out as the most popular month, with residents and visitors alike taking advantage of the lively community spirit. You'll find numerous events happening, making it a fantastic time to experience local culture and connect with fellow travellers.If you're looking for a more budget-friendly option, consider visiting in October. This month presents a lovely opportunity to enjoy the beautiful autumn foliage without the crowds, making it superb for leisurely walks and scenic drives. The peacefulness of fall can enhance your experience, allowing for reflection and relaxation amidst the vibrant colours of the season.Ultimately, the timing of your visit to Leaside hinges on your preferences—whether you want the energy and excitement of summer or the calm and beauty of autumn.
Are there any remote work holiday rentals in Leaside?
In Leaside, Ontario, there are around 18 remote work-friendly holiday rentals available, making it a suitable destination for those looking to combine work and leisure. Many of these properties come equipped with essential amenities for remote work, such as dedicated desks, complimentary Wi-Fi, and comfortable desk chairs.The neighbourhood itself is known for its tranquil residential atmosphere, with nearby parks providing a pleasant backdrop for breaks from work. Leaside's proximity to downtown Toronto means that you can easily explore local cafés and restaurants during your downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are the top attractions in Leaside, Ontario, Canada?
In Leaside, Ontario, visitors can enjoy several attractions that showcase the charm of this suburban neighbourhood. The Leaside Gardens, for instance, is a popular spot featuring an arena and a community centre, where locals engage in various sports and activities. The nearby Serena Gundy Park offers scenic walking trails and lush greenery, great for leisurely strolls or picnics.Another highlight is the Leaside Village, a shopping area with a mix of boutiques, cafés, and restaurants, providing a vibrant local atmosphere. The area is also well-connected to the Bayview Extension, which allows for easy access to downtown Toronto and its numerous attractions.
Are all fees included in the Leaside 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 Leaside holiday homes with parking?
Stayz offers a wide selection of holiday homes in Leaside 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 Leaside holiday homes?
You can find great discounts on holiday homes in Leaside 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 Leaside holiday home booking on Stayz?
To find Leaside 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 Leaside?
A long-stay holiday home in Leaside 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 Leaside holiday home?
Book your Leaside 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 Leaside?
Prices for holiday homes in Leaside 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 Leaside 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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