Simcoe County Rentals by Owner
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $197/Night
For 7 Nights CA $1,380
10763.91 ft²
4 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Private Pool
- Oceanfront
- Hot Tub
CA $257/Night
For 7 Nights CA $1,799
CA $232/Night
For 7 Nights CA $1,623
400 ft²
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $207/Night
For 7 Nights CA $1,450
10763.91 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Oceanfront
- Skiing
- Fireplace/Heating
CA $454/Night
For 7 Nights CA $3,176
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $399/Night
For 7 Nights CA $2,796
2454.17 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Parking
- Air Conditioner
- Internet
CA $289/Night
For 7 Nights CA $2,024
950 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $100/Night
For 7 Nights CA $697
1001.04 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Parking
- Air Conditioner
CA $107/Night
For 7 Nights CA $749
500 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
CA $206/Night
For 7 Nights CA $1,444
CA $333/Night
For 7 Nights CA $2,333
1200 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $113/Night
For 7 Nights CA $791
Why Choose Rent By Owner for your Simcoe County vacation rental?
What makes our Rentals by Owner special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Simcoe County
When should you plan your Rentals by Owner stay?
Choosing the right time to visit ensures you experience the region's unique charm at its best, whether you're seeking the lively energy of peak seasons or a peaceful retreat during quieter months in Simcoe County, Ontario.
Peak Season Highlights
Summer (June to August)
During the warmest months, you'll find this area bustling with outdoor activities and vibrant local events, making it ideal for a lively getaway.
Average Temperature Daytime: 22°C to 28°C - Nighttime: 14°C to 18°C
Fall (September to November)
Autumn offers spectacular scenery as the leaves change colors, perfect for scenic drives or outdoor exploration in this destination.
Average Temperature Daytime: 15°C to 20°C - Nighttime: 8°C to 12°C
Off-Season Highlights
Winter (December to February)
The cold winter months bring quieter times here, providing a cozy retreat with opportunities for winter sports and festive holiday experiences.
Average Temperature Daytime: -5°C to -1°C - Nighttime: -10°C to -15°C
Spring (March to May)
As the region awakens from winter, you can enjoy fewer crowds and the beauty of blooming flora, making it a peaceful time to visit and explore.
Average Temperature Daytime: 8°C to 15°C - Nighttime: 2°C to 7°C
Weekly Weather Forecast for Simcoe County
How to Book Your Simcoe County vacation rental
What's our booking process?
Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
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.
Explore and book the perfect rental in Simcoe County
Common Rentals by Owner Amenities
What amenities can you expect?
Our Rentals by Owner are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
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 outdoor dining with a fully equipped picnic area or barbecue grill.
- Relax by a private swimming pool or hot tub, ideal for unwinding after your daily adventures.
- Take advantage of expansive gardens or landscaped yards perfect for outdoor activities.
- Make the most of spacious patios or decks for morning coffee or evening gatherings.
- Explore nearby walking trails or nature paths that highlight the region’s scenic beauty.
- Utilize outdoor sports facilities such as volleyball courts or lawn game areas.
- Benefit from ample parking space or covered carports designed to accommodate your transportation needs.
Top Attractions Around Simcoe County
What attractions are nearby?
In this region, you can explore a variety of outdoor activities and cultural experiences that showcase the natural beauty and local heritage, making your stay truly memorable and enriching.
Family Activities
- Simcoe County Museum: Explore local history through engaging exhibits and outdoor activities that are perfect for family visits in the area.
- Treetop Trekking: Experience an exciting adventure with treetop obstacle courses designed to challenge and entertain children and adults alike.
- Discovery Harbour: Step back in time at this historic site where families can enjoy guided tours and interactive displays on regional maritime history.
- Bass Lake Provincial Nature Reserve: Enjoy a day of outdoor fun with hiking, picnicking, and wildlife viewing at this natural gem within the region.
Adult Activities
- Exploring the Local Art Galleries: Immerse yourself in the region’s vibrant arts scene by visiting local galleries that showcase talented regional artists, perfect for a relaxing cultural experience.
- Hiking and Nature Walks: Discover the area's scenic trails and lush landscapes, offering you an ideal opportunity to enjoy outdoor activities amidst picturesque surroundings.
- Wineries and Vineyard Tours: Experience wine tasting sessions at nearby wineries, where you can learn about local viticulture and savor regional varietals firsthand.
- Golfing on Regional Courses: Tee off at well-maintained golf courses designed to challenge players of all skill levels while enjoying the natural beauty of the destination.
Other Places to Stay in Simcoe County, ON
Central Ontario
Barrie - Orillia
Wasaga Beach
Innisfil
Collingwood
Oro-Medonte
Barrie
Orillia
Alcona
Severn
Simcoe County Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Nature: Take advantage of the area's scenic parks and outdoor trails to fully experience the natural beauty that surrounds your rental, enhancing your stay in this region.
- Connect with Hosts: Communicate directly with your rental owner to receive personalized tips and ensure your needs are met, making your visit here more comfortable.
- Plan Activities Ahead: Research popular local events and attractions beforehand to maximize your time and enjoy all that the area has to offer during your trip.
- Utilize Nearby Amenities: Stay close to essential amenities and services by choosing rentals in well-situated locations, simplifying your daily routines while exploring this destination.
Transportation Options
- Simcoe County Transit: Offers comprehensive bus services connecting key towns and rural areas, making it easy to explore the region without a car.
- Regional Airport: Provides convenient air travel options for visitors arriving from other parts of Ontario and beyond, facilitating quick access to your rental accommodations.
- Taxi and Ride-Sharing Services: Reliable taxi and ride-sharing providers operate throughout here, offering flexible transportation solutions for personalized trips and short-distance travel.
- Car Rentals: Numerous rental agencies serve the area, giving you the freedom to discover hidden gems and scenic spots at your own pace during your stay.
Local Customs Options
- Respect for Indigenous Lands: You will find that acknowledging and respecting the area's Indigenous heritage is an important custom here, often seen in local events and community traditions.
- Festivals and Seasonal Celebrations: Participating in regional festivals celebrates local culture and history, offering an authentic experience during your stay in the region.
- Community Hospitality: Visitors are often welcomed warmly, with locals showing genuine hospitality that reflects the area's friendly and inclusive atmosphere.
- Environmental Stewardship: Emphasizing conservation and outdoor respect, it’s customary to follow eco-friendly practices when enjoying the natural beauty of this destination.
Frequently Asked Questions About Simcoe County Rentals by Owner
1. What are the top Vacation Rentals in Simcoe County?
There are a lot of options in Simcoe County. If you plan on staying in the Simcoe County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Simcoe County:
- HOT TUB-Natural paradise, timber frame, sauna, close to Casino and ski hill.
- 2 minute walk to beach. 30 minute drive to Blue Mountain ski resort.
- Beautiful & Private Mid Century Modern Country-House on 10 Acres near Caledon!
- Amazing fully upgraded 3 bedroom+ new furniture, 1 full bath lake property
- Lake Simcoe 4-Bedroom Home 5 Minutes to Beach Park
- Modern 5-bedroom house close to Ski and Forest Trails
- Stunning Waterfront Luxurious Lakehouse 45 mins from Toronto! Great for families
- Spectacular Waterfront three Bedroom Home!
- Luxury Beach House With Incredible Sunset Views
- Luxury Beach House - Steps To Wasaga Beach
2. How many Vacation Rentals are available in Simcoe County?
Currently, the total number of properties listed by RBO in 2026 is over 1662 in the Simcoe County area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Vacation Rentals in Simcoe County.
3. What is the cancellation policy for a rental by owner in Simcoe County?
The cancellation policy varies depending on the specific listing. It’s important to review the cancellation terms directly on the rental’s page or contact the owner for detailed information before booking.
4. How do I communicate with the owner of a rental property in Simcoe County before booking?
You can reach out to the owner through the messaging system provided on the listing platform. This allows you to ask questions, confirm details, and ensure the property meets your needs before finalizing your reservation.
5. Are there any specific check-in or check-out procedures for rentals in the region?
Check-in and check-out procedures are outlined in each listing. To ensure a smooth arrival and departure, review these details carefully or contact the owner if you have specific questions about the process.
6. What amenities are typically included in private rentals here?
Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, and parking. For a complete list, please refer to the individual listing or contact the owner directly for clarification.
7. How do I verify the safety and quality standards of a rental by owner in this area?
All listings are reviewed for accuracy and legitimacy on the platform, but it’s recommended to read guest reviews and ask the owner about safety features to ensure the property meets your expectations before booking.
More Rentals You May Like Near Simcoe County
3003.13 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Parking
CA $661/Night
For 7 Nights CA $4,624
915 ft²
6 Guests
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Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $345/Night
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400 ft²
2 Guests
1 Bedroom
1 Bathroom
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- Hot Tub
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- Balcony/Terrace
CA $273/Night
For 7 Nights CA $1,911
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
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- Fireplace/Heating
- Kitchen
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CA $344/Night
For 7 Nights CA $2,407
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
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- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $151/Night
For 7 Nights CA $1,056
500 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $152/Night
For 7 Nights CA $1,065
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $108/Night
For 7 Nights CA $758
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
CA $482/Night
For 7 Nights CA $3,377
1250 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $399/Night
For 7 Nights CA $2,794
750 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Apartment
- Fireplace/Heating
- Pool
- Ocean View
CA $347/Night
For 7 Nights CA $2,426
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $340/Night
For 7 Nights CA $2,378
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
CA $298/Night
For 7 Nights CA $2,089
