Simcoe County Vacation Rentals with Pools
Condo
10.0(86 Reviews)
1 Bedroom
1 Bath
4 Guests
630 ft²
Oceanfront
Fireplace/Heating
Pool
Ocean View
US $161/Night
7 Nights - US $1,127
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
Condo
2.0(1 Review)
1 Bedroom
1 Bath
4 Guests
6458 ft²
- Spa
Skiing- Fireplace/Heating
- Pool
US $168/Night
7 Nights - US $1,178
Condo
10.0(21 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Fireplace/Heating
- Pool
- Ocean View
Balcony/Terrace
US $141/Night
7 Nights - US $988
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
Ski Chalet
10.0(18 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $229/Night
7 Nights - US $1,603
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
Condo
10.0(16 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $234/Night
7 Nights - US $1,635
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
839.58 ft²
- Private Beach
- Oceanfront
- Skiing
- Fireplace/Heating
US $395/Night
7 Nights - US $2,765
House
10.0(15 Reviews)
1 Bedroom
1 Bath
3 Guests
500 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $165/Night
7 Nights - US $1,156
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
House
10.0(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
915 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $236/Night
7 Nights - US $1,655
Why Choose Rent By Owner for your Simcoe County Vacation Rentals with Pools?
What makes our Vacation Rentals with Pools 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.
Weekly Weather Forecast for Simcoe County
How to Book Your Simcoe County Vacation Rentals with Pools
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals with pools. 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 with Pools Amenities
What amenities can you expect?
Our Vacation Rentals with Pools 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
Other Places to Stay in Simcoe County, ON
Central Ontario
Barrie - Orillia
Wasaga Beach
Innisfil
Collingwood
Oro-Medonte
Barrie
Ramara
Severn
Alcona
Orillia
Frequently Asked Questions About Simcoe County Rentals with Pools
1. What are the top Rentals With Pools 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 Rentals With Pools in Simcoe County:
- Beautiful & Private Mid Century Modern Country-House on 10 Acres near Caledon!
- STUNNING LAKEFRONT VIEWS. Beautiful, ground floor unit. Lighthouse Point.
- The Blue House - 4 Bedrooms + Pool - Perfect for the Whole Family!
- Georgian Bay waterfront cottage in a quiet cove w/HOT TUB
- Two units in Horseshoe Valley
- Cottage on quiet lake, great for swimming, fishing, boating
- Friday Harbour Prime Location - Luxurious Lakeside Escape
- Luxury Lake Simcoe Waterfront Cottage
- Stunning Modern Beach/Ski House
- The Mansion, Wasaga beach, Blue mountain
2. How many Rentals With Pools are available in Simcoe County?
Currently, the total number of properties listed by RBO in 2026 is over 539 in the Simcoe County area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Simcoe County.
More Rentals You May Like Near Simcoe County
House
9.8(7 Reviews)
2 Bedrooms
3 Baths
6 Guests
904.17 ft²
- Oceanfront
- Hot Tub
- Skiing
- Fireplace/Heating
US $176/Night
7 Nights - US $1,231
Condo
10.0(11 Reviews)
2 Bedrooms
2 Baths
5 Guests
850 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $183/Night
7 Nights - US $1,282
Condo
10.0(7 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $139/Night
7 Nights - US $971
Condo
10.0(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $154/Night
7 Nights - US $1,078
Apartment
10.0(4 Reviews)
2 Bedrooms
3 Baths
6 Guests
750 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $240/Night
7 Nights - US $1,678
House
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $194/Night
7 Nights - US $1,356
Condo
10.0(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $98/Night
7 Nights - US $688
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
4 Guests
350 ft²
- Hot Tub
- Spa
- Skiing
- Fireplace/Heating
US $88/Night
7 Nights - US $616
Condo
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $218/Night
7 Nights - US $1,527
Condo
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $177/Night
7 Nights - US $1,239
Condo
10.0(2 Reviews)
3 Bedrooms
1 Bath
6 Guests
1050 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $60/Night
7 Nights - US $419
Condo
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $446/Night
7 Nights - US $3,122
