Simcoe County Vacation Home Rentals from CA $271: Search Top Private Vacation Homes for Rent

A hillside with autumn foliage, a rocky cliff, and a field of wildflowers.

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Top Cities in Simcoe County

A historic brick building with green shutters and a sign for 'Arcade'.

Our top choices for Simcoe County vacation homes

An indoor swimming pool with clear glass walls, a tiled floor, and a high ceiling with wooden beams.

1. Horseshoe Valley Suites - The Glade

Oro-Medonte

Elizabeth

A two-story house with a front porch, a brick facade, and a symmetrical garden with white flowers and hedges.

2. Charming, private 1 BR - just mins to Collingwood!

Collingwood

Mike A.

An aerial view of a coastal property with multiple houses, a clear beach, and a rocky shoreline.

3. Cottage tiny heaven.

Tiny

Manesha P.

A large house with a swimming pool, surrounded by dense trees and a well-maintained garden.

4. The Mansion, Wasaga beach, Blue mountain

Utopia

Anonymous traveller

CA $2,200 total

includes taxes & fees

Aug 31 - Sep 1

A living room with a leather sofa, a coffee table, a fireplace, and a television.

5. 6 Bedroom Large Family Home near Lake Simcoe & Innisfil Beach - Patio & BBQ

Alcona

Somar A.

A spacious living area with a large fireplace, a dark sectional sofa, and a staircase leading to an upper level.

6. Modern Luxury Retreat with Stunning Views & Open Concept Design

severn

Angue

CA $1,123 total

includes taxes & fees

Sep 1 - Sep 2

A brick house with a central entrance, two satellite dishes, and a chimney.

7. Clearview Ranch Estates Full House

Stayner

8. The 1883 Century Hotel Suite

Collingwood

Robert

CA $271 total

includes taxes & fees

Sep 21 - Sep 22

A hallway with a wooden staircase, white walls, and a tiled floor.

9. Modern 2BR Smart Home, Designed for Ease—Mins to Shops, Dining & Innisfil Beach!

Innisfil

Isabella S.

CA $426 total

includes taxes & fees

Aug 31 - Sep 1

A spacious living room with a fireplace, a staircase, and a large window.

10. Luxury Georgian Bay Retreat Heated Pool, Hot Tub, Sauna + Trails Near the Lake

Midland

Cheryl K.

A modern kitchen with a central island, wooden staircase, and a dining area with white chairs.

11. Vacation Inn Townhomes

Collingwood

Linda

CA $497 total

includes taxes & fees

Sep 21 - Sep 22

A wooden deck with a hot tub, a grill, and outdoor seating.

12. Georgian Bay Cottage- Hot Tub/Sauna/Trail/Run/Bike/Swim//Marina!

Waubaushene

Colette C.

A beach with a clear sky, sandy shore, and a few boats in the water.

13. 3-Min Walk to Sandy Beach | 3BR Georgian Bay Cottage | Fire Pit + BBQ!

Penetanguishene

kevork v.

A clean, modern hallway with a white door leading outside, a large mirror on the right, and a dark staircase on the left.

14. Golf course Access, 5mins to Main Beach, Wasaga 500 (Go-Kart, Batting Cage)

Wasaga Beach

A bedroom with a bed, a nightstand, a ceiling fan, a window with curtains, and a view of greenery outside.

15. Beach1 Waterfront Stunning Views

Wasaga Beach

"We liked the closeness to the beach Was told prior to arrival, the cleaning staff had entered at 11am, the arrived when I was entering at approx .4:30pm. It was dirty with dog hair on the floors, sofa and pillows. The balcony off the livingroom was full of at least 4 day old Pidgeon feces, also on the other two balconies. Maintenance cleaned one WHILE we were there, the other two the next day.. The garage door was defective. Cleaning staff fixed it initially, it happened again after entering...

Deanna

An outdoor deck with wicker furniture, a table, and a view of a lake and distant buildings.

16. Little Lake Escape | Waterfront 2 Bedroom Getaway

Midland

"I reserved this property for a two-night stay seeking a tranquil retreat, and it certainly met my expectations! The residence was impeccably maintained, and the panoramic views from the backyard were truly stunning. The firepit offered a comforting warmth, enhancing the experience of observing the sunset over the lake. The hosts provided all essential information for my stay, facilitating a seamless check-in process upon my arrival. Furthermore, their responsiveness to my inquiries was...

T. J.

A modern kitchen with a bar area, wooden beams, and large windows.

17. Campfire, Privacy, Stargazing minutes to Beaches/Orillia/Casino Rama

Orillia

jacob m.

A lakeside deck with Adirondack chairs and a wooden deck.

18. Cozy Lake Simcoe Waterfront Escape for 10

Innisfil

Robert

A cozy cabin interior with a gray sofa, wooden dining table, and chairs.

19. 3bdrm Cottage at Lake Simcoe

Brechin

Ryan R.

A sandy beach with footprints, a clear sky, and a calm sea.

20. Life's a Beach House -Perfect beachfront vacation rental

Tiny

"We had a wonderful stay at this property! We were six adults travelling with our dog, and there was plenty of space for everyone to be comfortable. The home was spotless, well-maintained, and had everything we needed. The host was excellent with communication, making the entire stay smooth and stress-free. The beach was beautiful and a real highlight of our trip. We had a fantastic time and would definitely return. We highly recommend this property to anyone looking for a relaxing and enjoyable...

Pino M.

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