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  3. Toronto
  4. Streetsville
  5. Rentals by Owner

Streetsville Rentals by Owner

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4.8 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
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10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety

Why Choose Rent By Owner for your Streetsville vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Streetsville

When should you plan your Rentals by Owner stay?

Understanding the best time to visit here can help you maximize your experience and enjoy the area’s unique charm when planning your vacation through Rent By Owner in Streetsville, Mississauga, Ontario.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, you'll experience the area's lively atmosphere and longer daylight hours, making it ideal for exploring local outdoor amenities while staying in rental homes here.

Average Temperature Daytime: around 25°C - Nighttime: around 15°C
autumn
Fall (September to November)

Autumn offers a pleasant climate with scenic foliage, creating a charming setting for your stay. This season is perfect for enjoying the area's natural beauty while booking a comfortable rental by owner.

Average Temperature Daytime: around 18°C - Nighttime: around 8°C

Off-Season Highlights

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Winter (December to February)

The winter months bring cooler temperatures and quieter surroundings, providing a peaceful atmosphere for those seeking a cozy getaway in this region.

Average Temperature Daytime: around -2°C - Nighttime: around -10°C
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Spring (March to May)

Early spring sees milder weather and fewer visitors, offering an affordable time to book rental accommodations while enjoying the area's emerging natural beauty.

Average Temperature Daytime: around 10°C - Nighttime: around 3°C

Weekly Weather Forecast for Streetsville

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

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

  • Enjoy private outdoor patios or decks perfect for relaxing and dining al fresco.
  • Take advantage of shared garden areas or lush lawns to unwind amidst nature.
  • Make use of designated grilling or barbecue stations for outdoor cooking experiences.
  • Utilize nearby walking trails or pathways for scenic strolls through the area’s natural beauty.
  • Benefit from outdoor parking spaces that provide convenient access to your rental.
  • Explore communal outdoor swimming pools or hot tubs available at some properties.
  • Discover spacious yards ideal for outdoor activities or family gatherings in this welcoming destination.
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Family Activities

  • Streetsville Memorial Park: Enjoy a relaxing day outdoors with family-friendly picnic areas, walking trails, and playgrounds in this scenic park within the region.
  • Village Square: Explore this charming historic area featuring local shops, seasonal events, and community activities perfect for family outings.
  • local Farmers' Market: Visit the farmers' market during peak seasons to experience fresh produce, artisanal goods, and engaging activities for kids.
  • Walking Tours of Streetsville Heritage District: Discover the area's rich history on guided or self-paced walks through streets lined with heritage buildings and landmarks.
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Adult Activities

  • Streetsville Historic District Tour: Discover the charm of the area's well-preserved architecture and vibrant local history through a guided walk, perfect for immersing yourself in the community’s heritage.
  • Local Wineries and Craft Breweries: Explore nearby wineries and craft breweries that offer tastings and tours, providing a relaxing way to enjoy the region's renowned beverage scene.
  • Golfing at Local Courses: Play a round on the area’s scenic golf courses, where you can enjoy lush fairways and beautiful landscapes in a peaceful setting.
  • Shopping at Streetsville Town Square: Browse unique boutiques and artisan shops in the town square, making it an ideal spot to find one-of-a-kind souvenirs or enjoy a leisurely day out.

Streetsville Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit Around Local Events: Check the area’s event calendar to align your stay with community festivals or markets that showcase the region’s charm and culture.
  • Explore Nearby Dining Options: Take advantage of the local eateries to enjoy authentic flavors and get a true taste of what makes this destination unique.
  • Utilize Public Transportation or Walk: Maximize your experience by exploring the area on foot or via public transit, allowing you to discover hidden gems effortlessly.
  • Communicate with Your Host for Insider Tips: Reach out to your rental host to receive personalized recommendations for the best local attractions and experiences here in the region.

Transportation Options

  • Mississauga Transit: Provides reliable bus services throughout the area, making it easy to explore streets and other neighborhoods within this region.
  • GO Transit: Offers convenient commuter train and bus options connecting you to Toronto and surrounding cities, ideal for day trips or work commutes in the region.
  • Private Car Rentals: Several local agencies offer car rentals that give you flexibility to navigate Streetsville and its nearby attractions at your own pace.
  • Taxis and Rideshare Services: Available throughout the area, these services provide quick, on-demand transportation options for seamless travel around Streetsville and beyond.

Local Customs Options

  • Community Celebrations: Participating in local festivals and parades reflects the area's strong tradition of community engagement and hospitality.
  • Respect for Heritage: Honoring the region's history through preservation efforts and cultural displays showcases the area's pride in its roots.
  • Dining Etiquette: Embracing the local dining customs, such as sharing meals during gatherings, enhances your experience here.
  • Local Art and Craftsmanship: Supporting artisans and engaging with handcrafted goods demonstrates appreciation for the area's creative spirit.

Frequently Asked Questions About Streetsville Rentals by Owner

2. How many Rentbyowner vacation rentals are available in Streetsville?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 354 in the Streetsville 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 Streetsville. 

3. What is the cancellation policy for rentals by owner in Streetsville, Mississauga?

Cancellation policies vary depending on the individual listing. You should review the specific rental's terms on the listing page or contact the owner directly to understand the cancellation options and any applicable fees.

4. How do I communicate with the property owner before booking in this region?

You can typically contact the owner through the messaging platform provided by the booking site. For detailed questions about the property or special requests, reaching out directly ensures clear communication.

5. Are there any specific house rules I need to follow during my stay?

Yes, each rental by owner usually has its own set of house rules outlined in the listing. Be sure to read these carefully before booking and contact the owner if you have any questions.

6. Is a security deposit required when booking a rental in this area?

Many owners request a security deposit to cover potential damages or extra cleaning. The amount and conditions are specified in the listing, so reviewing this information will help you prepare accordingly.

7. What amenities are typically included in a rental by owner here?

Amenities vary between listings but often include essentials like Wi-Fi, parking, and kitchen access. Check the specific property details on the listing page to ensure it meets your needs.

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