Best Vacation Homes in Simcoe County
Condo
10.0(86 Reviews)
1 Bedroom
1 Bath
4 Guests
630 ft²
Oceanfront
Fireplace/Heating
Pool
Ocean View
US $155/Night
7 Nights - US $1,082
House
10.0(17 Reviews)
1 Bedroom
1 Bath
4 Guests
10763.91 ft²
Private Pool- Oceanfront
Hot Tub
Spa
US $188/Night
7 Nights - US $1,319
House
10.0(3 Reviews)
1 Bedroom
1 Bath
- Spa
- Fireplace/Heating
Balcony/Terrace
Breakfast
US $171/Night
7 Nights - US $1,194
Apartment
10.0(45 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $130/Night
7 Nights - US $912
Villa
10.0(8 Reviews)
3 Bedrooms
3 Baths
6 Guests
10763.91 ft²
- Oceanfront
Skiing- Fireplace/Heating
- Ocean View
US $333/Night
7 Nights - US $2,329
Cottage
10.0(36 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly
Kitchen
US $181/Night
7 Nights - US $1,266
Cabin
10.0(32 Reviews)
1 Bedroom
1 Bath
5 Guests
400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $152/Night
7 Nights - US $1,063
House
10.0(31 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $294/Night
7 Nights - US $2,056
Simcoe County Luxury Rentals
US $6,611/Night
7 Nights - US $46,274
Cottage
8 Bedrooms
7 Baths
18 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
US $5,789/Night
7 Nights - US $40,525
Cottage
6 Bedrooms
4 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
Air Conditioner
Internet
US $5,005/Night
7 Nights - US $35,036
Other
5 Bedrooms
7 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $3,830/Night
7 Nights - US $26,811
Cottage
10.0(6 Reviews)
3 Bedrooms
4 Baths
14 Guests
7000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Spa
US $3,255/Night
7 Nights - US $22,788
Other
5 Bedrooms
3 Baths
14 Guests
4100 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $3,248/Night
7 Nights - US $22,739
House
7 Bedrooms
5 Baths
14 Guests
4000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $3,102/Night
7 Nights - US $21,714
Cottage
14 Bedrooms
5 Baths
31 Guests
2691 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $3,061/Night
7 Nights - US $21,424
Simcoe County Pet Friendly Vacation Rentals
House
10.0(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
915 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $263/Night
7 Nights - US $1,838
House
10.0(3 Reviews)
2 Bedrooms
3 Baths
6 Guests
904.17 ft²
- Oceanfront
- Hot Tub
- Spa
- Skiing
US $244/Night
7 Nights - US $1,711
Cottage
10.0(1 Review)
5 Bedrooms
3 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $694/Night
7 Nights - US $4,858
Cottage
10.0(11 Reviews)
2 Bedrooms
1 Bath
4 Guests
1302 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $239/Night
7 Nights - US $1,672
House
10.0(2 Reviews)
4 Bedrooms
4 Baths
8 Guests
3003.13 ft²
- Balcony/Terrace
- Pet Friendly
Parking- Air Conditioner
US $484/Night
7 Nights - US $3,391
House
10.0(11 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $200/Night
7 Nights - US $1,401
Condo
10.0(10 Reviews)
2 Bedrooms
2 Baths
5 Guests
850 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $183/Night
7 Nights - US $1,282
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
1250 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $312/Night
7 Nights - US $2,187
Simcoe County Large Vacation Homes
Villa
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
US $91/Night
7 Nights - US $640
Apartment
10.0(1 Review)
5 Bedrooms
5 Baths
10 Guests
3003.13 ft²
Private Beach- Oceanfront
- Spa
- Skiing
US $1,063/Night
7 Nights - US $7,442
US $238/Night
7 Nights - US $1,668
Villa
9.2(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
915 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $239/Night
7 Nights - US $1,671
House
10.0(1 Review)
6 Bedrooms
1 Bath
5 Guests
1194.79 ft²
- Fireplace/Heating
- Pool
- View
- Parking
US $184/Night
7 Nights - US $1,291
Villa
8.6(7 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $152/Night
7 Nights - US $1,067
Condo
7.4(3 Reviews)
1 Bedroom
2 Baths
10 Guests
- Skiing
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $313/Night
7 Nights - US $2,192
Villa
6.0(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
915 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $272/Night
7 Nights - US $1,906
Why Choose Rent By Owner for your Simcoe County Vacation Rental Homes?
What makes our Vacation Rentals 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 Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as the region offers distinct attractions and activities throughout each season that perfectly complement your vacation plans.
Peak Season Highlights
Summer (June to August)
During the warm summer months, you'll enjoy the region's lush landscapes and vibrant outdoor activities, making it an ideal time to explore this destination’s natural beauty.
Average Temperature Daytime: 22°C to 28°C - Nighttime: 13°C to 17°C
Fall (September to November)
As the foliage transforms, the area offers stunning autumn scenery, perfect for scenic drives and outdoor adventures while experiencing pleasant weather.
Average Temperature Daytime: 15°C to 21°C - Nighttime: 7°C to 12°C
Off-Season Highlights
Winter (December to February)
This quiet season provides a peaceful retreat with opportunities for winter sports and cozy stays in your preferred vacation rentals in the region.
Average Temperature Daytime: -3°C to -8°C - Nighttime: -10°C to -15°C
Spring (March to May)
As the landscape begins to bloom, you can enjoy fewer crowds and mild weather, making it a great time to visit and relax in comfortable accommodations.
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 Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. 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 Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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 private barbecue grill available at many properties in the area.
- Relax by a scenic fire pit, perfect for cozy evenings under the stars.
- Take advantage of spacious yards, ideal for outdoor games and family activities.
- Access nearby lakes or rivers for kayaking, canoeing, or paddleboarding experiences.
- Benefit from well-maintained patios or decks, offering great spots to unwind and admire natural surroundings.
- Explore extensive gardens or landscaped grounds that enhance your outdoor living experience.
- Discover outdoor swimming pools often included in vacation rentals here, providing refreshing relief during warmer months.
Top Attractions Around Simcoe County
What attractions are nearby?
During your stay, you'll discover a variety of outdoor activities and local attractions nearby that allow you to fully experience the natural beauty and cultural charm of this region.
Family Activities
- Discovery Harbour: Explore this historic site where you and your family can learn about the region's maritime history through engaging exhibits and scenic waterfront views.
- Barrie Waterfront Trail: Stroll or bike along this picturesque trail, offering beautiful lakefront scenery and outdoor activities suited for all ages in the area.
- Heritage Park & Cultural Centre: Enjoy interactive exhibits, seasonal festivals, and hands-on activities that celebrate the local culture perfect for a family day out.
- Skiing and Snowboarding at Snow Valley: During winter months, hit the slopes and enjoy family-friendly skiing and snowboarding experiences at this popular ski resort in the region.
Adult Activities
- Exploring the outdoors at the Simcoe County Forests: You can enjoy hiking and wildlife watching in this expansive natural area that showcases the region's rich ecology.
- Visiting the historical sites in Barrie: Discover the area's heritage by exploring local museums and landmarks that highlight its cultural history.
- Enjoying water activities at Lake Simcoe: Relax or entertain yourself with boating, fishing, or swimming along the scenic shores of this popular destination.
- Experiencing local arts and culture: Attend performances and visit galleries that reflect the vibrant creative scene found throughout the region.
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 Attractions: Take advantage of the area's natural beauty and cultural sites to enrich your stay in Simcoe County.
- Plan Outdoor Activities: Engage in outdoor pursuits like hiking, boating, or fishing to fully experience this destination’s scenic landscapes.
- Enjoy Seasonal Events: Check out local festivals and seasonal activities to add a memorable touch to your visit here.
- Select the Right Accommodation: Choose a well-reviewed vacation rental that offers comfort and convenience to maximize your time exploring the region.
Transportation Options
- Simcoe County Transit: A reliable bus system offering connectivity across the area, making it easy for you to explore your surroundings during your stay.
- Ontario Northland Motor Coach: Providing long-distance travel options that connect here to major cities, ideal for day trips or extended journeys.
- Local Taxi Services: Convenient and readily available, these services can help you navigate the region comfortably when you prefer door-to-door transportation.
- Private Car Rentals: Renting a vehicle grants you the flexibility to explore this destination at your own pace and visit its scenic outdoor spots with ease.
Local Customs Options
- Loyalist Heritage: You can explore the area's deep roots by appreciating the Loyalist history that shaped the local community and its traditions.
- Farmers' Markets: Visiting local farmers' markets offers you a taste of regional produce and an authentic glimpse into the area's farming heritage.
- Indigenous Traditions: Respect for Indigenous cultures is essential here, with opportunities to learn about their history and ongoing contributions to the region.
- Seasonal Festivals: Participating in seasonal festivals allows you to experience the vibrant local customs and community spirit throughout the year.
Simcoe County Vacation Rental Frequently Asked Questions
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.
- Essence Suites Modern Condo *Collingwood *King Bed *Lake *Beach *Mountains *Spa
- Charming, private 1 BR - just mins to Collingwood!
- Private Queen Bed Studio near hiking, biking, golf, beach, spa and Blue Mountain
- 2 minute walk to beach. 30 minute drive to Blue Mountain ski resort.
- Modern Waterfront Lake House with it's own beach on Georgian Bay
- Beautiful & Private Mid Century Modern Country-House on 10 Acres near Caledon!
- Guest house close to Blue Mountain, Wasaga Beach and Collingwood!
- Truly a slice of heaven a must see!
- Country Cabin Escape | King Bed | Pet Friendly
2. How many vacation rentals have private pools in Simcoe County?
There are 111 vacation rentals with private pools near Simcoe County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Simcoe County are best for families?
If you are looking for a family-friendly vacation home in Simcoe County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Simcoe County:
4. How many Rentbyowner vacation rentals are available in Simcoe County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 2779 in the Simcoe County 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 Simcoe County.
5. What is the cancellation policy for vacation rentals in this region?
Cancellation policies vary depending on the property listing. You should review the specific terms provided on each rental's page or contact the property owner directly for detailed information about cancellations and potential fees.
6. How do I ensure my booking in the area is secure and reliable?
Bookings are made through a trusted platform that offers secure payment options and verified listings. Always read reviews and confirm the property details before completing your reservation to ensure a dependable stay.
7. Are there any additional fees or deposits required when booking here?
Additional fees and security deposits may apply, depending on the property. Check the listing details carefully or reach out to the owner to understand all costs involved before confirming your reservation.
8. What amenities should I expect from vacation rentals in this destination?
Amenities vary by property, but many include essentials like Wi-Fi, kitchen facilities, and parking. For specific features, review the property description or contact the host directly.
9. How far in advance should I book my stay to secure the best available options?
It’s recommended to book several weeks to months ahead, especially during peak seasons. Early planning helps you access the widest selection of accommodations and ensures availability for your preferred dates.
Simcoe County Top Rated Vacation Rentals
House
10.0(37 Reviews)
4 Bedrooms
2 Baths
7 Guests
3000 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $367/Night
7 Nights - US $2,569
Condo
10.0(18 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $144/Night
7 Nights - US $1,005
Ski Chalet
10.0(17 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $259/Night
7 Nights - US $1,814
Ski Chalet
10.0(16 Reviews)
3 Bedrooms
2 Baths
5 Guests
1338 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $116/Night
7 Nights - US $813
Condo
10.0(15 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $234/Night
7 Nights - US $1,638
House
10.0(14 Reviews)
1 Bedroom
1 Bath
3 Guests
500 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $151/Night
7 Nights - US $1,059
House
10.0(13 Reviews)
4 Bedrooms
2 Baths
9 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $434/Night
7 Nights - US $3,041
Cottage
10.0(12 Reviews)
4 Bedrooms
2 Baths
12 Guests
3000 ft²
- Oceanfront
- Hot Tub
- Skiing
- Fireplace/Heating
US $618/Night
7 Nights - US $4,327
