Discover Your Ideal Rental by Owner in Leaside, Toronto for a Comfortable Stay
Discover Your Perfect Leaside Rentals by Owner
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Rentals by Owner
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Luxury Vacation Rentals
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Pet Friendly Vacation Rentals
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Sustainable Travel
Leaside Rentals by Owner
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- TV
- Wheelchair Accessible
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Accessibility
- Security/Safety
- TV
- Security/Safety
- Fireplace/Heating
- Air Conditioner
- Parking
- Wheelchair Accessible
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Accessibility
- Security/Safety
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Pet Friendly
- Pool
- Parking
- Pet Friendly
- TV
Why Choose Rent By Owner for your Leaside vacation rental?
What makes our Rentals by Owner special?
Popular Areas for Leaside Rentals by Owner
Where are the best neighborhoods to stay in Leaside?
Discover the charm of Leaside, Toronto, Ontario, Canada, by choosing the perfect neighborhood to stay in during your visit. This welcoming community offers a mix of tranquility and convenient access to city amenities, making it an ideal location for your next rental by owner. Whether you prefer a cozy residential area or easy proximity to local shops and parks, Leaside provides a reliable and comfortable base for exploring Toronto’s vibrant surroundings. Booking through Rent By Owner ensures you find trustworthy vacation rentals in this desirable neighborhood, delivering a seamless and dependable experience tailored to your travel needs.
North York
This part of the city offers convenient access to a variety of amenities and transportation options, making it an ideal area to stay for both leisure and business travelers exploring the broader region.
View 363+ Rentals in North YorkEast York
Known for its vibrant community atmosphere, the area provides a comfortable setting with easy transit connections for those looking to experience local life while remaining close to the city's main attractions.
View 80+ Rentals in East YorkMidtown Toronto
Positioned centrally, here you'll find a lively neighborhood that combines urban convenience with peaceful residential streets, perfect for visitors seeking a balanced stay near the city's core.
View 287+ Rentals in Midtown TorontoBennington Heights
This peaceful enclave offers a quiet retreat within close proximity to the city's amenities, making it suitable for travelers wanting a serene environment during their visit.
View 1370+ Rentals in Bennington HeightsGovernor's Bridge
Famous for its scenic surroundings, the area provides a charming setting with easy access to natural spaces and local conveniences, ideal for those who appreciate a peaceful neighborhood.
View 1427+ Rentals in Governor's BridgeThorncliffe Park
A diverse and dynamic part of the city, it offers excellent public transit options and community amenities, making it a practical choice for visitors wanting connectivity and local flavor.
View 487+ Rentals in Thorncliffe ParkMount Pleasant East
This upscale neighborhood boasts tree-lined streets and a welcoming ambiance, perfect for travelers seeking a refined yet accessible place to stay in the region.
View 342+ Rentals in Mount Pleasant EastMoore Park
Known for its family-friendly feel, this area offers a tranquil environment with nearby parks and local services, making it suitable for those looking for a relaxed and comfortable stay.
View 1635+ Rentals in Moore ParkBest Times to Visit Leaside
When should you plan your Rentals by Owner stay?
To ensure a memorable stay in this destination, it's important to consider the optimal times to visit when booking your rental by owner through Rent By Owner, as the local climate and seasonal events can greatly influence your experience here.
Peak Season Highlights
Summer (June to August)
During the summer months, the area experiences warm weather, making it ideal for outdoor activities and exploring local amenities. This is when rental properties tend to be in high demand.
Early Fall (September to October)
As early fall arrives, the region offers pleasant temperatures and vibrant foliage, attracting visitors looking for a comfortable yet scenic stay. Booking early ensures access to top rental options here.
Off-Season Highlights
Late Fall to Winter (November to February)
During this period, the area sees cooler temperatures and fewer visitors, providing a more relaxed rental experience. It’s a great time to find deals and enjoy quieter surroundings.
Early Spring (March to May)
As the region transitions into spring, temperatures begin to rise, and rental prices often become more accessible. It’s an excellent time for those seeking a peaceful visit before the peak season begins.
Weekly Weather Forecast for Leaside
How to Book Your Leaside vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Leaside
Common Rentals by Owner Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Access to a private or shared outdoor patio or deck for relaxing and dining outdoors.
- Beautiful landscaped gardens or yard spaces to enjoy the fresh air and local flora.
- Outdoor seating areas perfect for morning coffee or evening gatherings.
- Ample space for outdoor activities such as lawn games or picnics.
- Convenient parking facilities in close proximity to outdoor amenities.
- Secure outdoor storage for outdoor gear or recreational equipment.
- Proximity to nearby parks or green spaces that enhance your outdoor experience here.
Top Attractions Around Leaside
What attractions are nearby?
Within this vibrant region, you can explore a variety of outdoor activities and local attractions that showcase the best of Toronto’s diverse community, all easily accessible from your rental by owner in Leaside for a truly convenient and enjoyable stay.

Family Activities
- Leaside Park: You can enjoy outdoor family activities and sports at this popular local park, perfect for picnics and playground visits.
- Sunnybrook Park: Take a family stroll or bike ride through the scenic trails of this expansive green space nearby, offering a relaxing escape.
- Cineplex Cinemas in Leaside: Experience the latest blockbuster movies in a family-friendly environment right in the area.
- Local Community Events: Participate in seasonal festivals and community gatherings that bring families together throughout the year here.
Adult Activities
- Golfing at Leaside Golf Course: Experience a relaxing day on the greens at this local golf course, perfect for unwinding and enjoying the scenic surroundings.
- Visiting Sunnybrook Park: Explore the expansive park with its walking trails and outdoor activities, ideal for a leisurely day in the region's natural setting.
- Dining at Local Restaurants: Savor diverse culinary offerings at nearby eateries that showcase the area's vibrant food scene and welcoming atmosphere.
- Shopping at Bayview Village Shopping Centre: Discover a wide range of retail stores and boutiques just minutes from here, making it easy to indulge in some retail therapy.
Other Places to Stay in Leaside, ON
Leaside Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining options: Take time to discover nearby restaurants and cafes to experience the authentic flavors of this vibrant area.
- Utilize public transportation: Make the most of transit options around here to easily access Toronto’s key attractions and avoid parking hassles.
- Plan outdoor activities: Enjoy the region’s parks and green spaces to unwind and immerse yourself in the natural beauty of your surroundings.
- Communicate with your host: Reach out for personalized recommendations and insider tips to enhance your stay in this welcoming community.
Transportation Options
- Toronto Transit Commission (TTC) Subway and Bus Services: You can rely on the extensive TTC network for convenient access around the area and beyond, making your stay easily connected to Toronto's key attractions and neighborhoods.
- GO Transit Commuter Trains and Buses: For regional travel, GO Transit offers efficient train and bus routes that connect here with downtown Toronto and other parts of Ontario, ideal for day trips or commuting.
- Rideshare Services: Popular ride-hailing apps provide flexible transportation options within the region, giving you the ease of door-to-door service during your visit.
- Local Taxis and Private Car Rentals: Traditional taxis and private car rentals are readily available for direct, comfortable travel around this destination and surrounding neighborhoods.
Local Customs Options
- Respect for Local Heritage: You’ll notice a strong appreciation for the area's historical roots, often reflected in community events and preserved architecture.
- Community Engagement: Participating in neighborhood gatherings and local markets is common, fostering a welcoming atmosphere for visitors seeking an authentic experience.
- Environmental Awareness: Eco-friendly practices are valued here, with residents and visitors encouraged to minimize waste and support sustainable initiatives.
- Politeness and Courtesy: Courteous interactions and respectful behavior are often observed in everyday exchanges, highlighting the area's friendly community spirit.
Frequently Asked Questions About Leaside Rentals by Owner
1. What are the top vacation rentals in Leaside?
There are a lot of options in Leaside. If you plan on staying in the Leaside area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Leaside:
- Grand Victorian Suite - min 30 nights
- Toronto - Central Location, Classic Leaside Neighbourhood
- Crescent House - Luxury Residence in Rosedale, in the Heart of Toronto
- Unrivaled Location on Yorkville Ave 2000 sq.ft -1 BED.
- Hazelton Suites - Yorkville - Indoor Pool & Hot Tub
- Clean, white, bright and close to Woodbine subway
- Deluxe Yorkville Townhouse
- 4 BDRM Downtown House - Urban Elegance with 2 cars Garage
- Traveller home in centre Toronto
- Regis Suites - Downtown Toronto - CN Tower & Rogers Centre
2. How many Rentbyowner vacation rentals are available in Leaside?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 668 in the Leaside area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Leaside.
3. What is the cancellation policy for a rental by owner in this area?
4. How do I ensure the rental I book complies with safety standards?
5. Are there any additional fees I should be aware of when booking a rental in this region?
6. What is the check-in and check-out process for rentals here?
7. How can I verify the authenticity of a rental listing in this destination?
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