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Houses for Rent in Collingwood ON Under $500K

Showing results 1 - 29 of 29

Check out our extensive selection of houses under $500k for rent in Collingwood on Square Yards Canada. With over 29 options available, we provide a variety of affordable rental choices to suit your needs in different municipalities. Our listings offer detailed information about bedroom and bathroom configurations, as well as other amenities. Use our filters to search by budget, location, and features to find the perfect rental. You simply need to choose your desired budget range filter and you will be provided with the sorted options available for your range. Discover the best Simcoe houses for rent under Collingwood today and start your journey to affordable living with Square Yards Canada.

Last Updated: December 05, 2025

23 Photos

5 Spooner Crescent, Simcoe, ON , MLS #S12590562 , Image - 1

Unit-210, 5 Spooner Crescent Collingwood, Simcoe, ON MLS® S12590562

Residential Condo & Other (Condo Apartment)

$2800.0

2 Beds
2 Baths
1000-1199 sq-ft

Discover Your Dream Retreat in Collingwood Near Blue Mountain & Georgian Bay! Nestled in the Scenic Blue Fairview Development on Cranberry Golf Course

37 Photos

29 St. Clair Street, Simcoe, ON , MLS #S12170761 , Image - 1

29 St. Clair Street Collingwood, Simcoe, ON MLS® S12170761

Residential Freehold (Detached)

$12500.0

Reduced by 16.7%

5 Beds
4 Baths
2500-3000 sq-ft

Ski Season is Coming! Welcome to The Lake House - a bright & airy 5 bedroom lakeside retreat on the stunning shores of Georgian Bay, with a separate 1

24 Photos

452 Hurontario Street, Simcoe, ON , MLS #S12526470 , Image - 1

452 Hurontario Street Collingwood, Simcoe, ON MLS® S12526470

Residential Freehold (Detached)

$2300.0

Reduced by 14.8%

2 Beds
1 Baths
< 700 sq-ft

SKI SEASON RENTAL. Detached bungalow. 2 bedrooms & 1 bathroom. Oversized backyard! Walk to downtown Collingwood. Discover this stylish and contemporar

33 Photos

111 ELLEN Lane, Simcoe, ON , MLS #S12259571 , Image - 1

111 ELLEN Lane Collingwood, Simcoe, ON MLS® S12259571

Residential Condo & Other (Condo Townhouse)

$12000.0

Reduced by 14.3%

2 +2 Beds
3 Baths
1400-1599 sq-ft

SKI SEASON LEASE***INCLUSIVE OF UTILITIES AND PETS CONSIDERED***PRICE STATED IS FOR THE SEASON. This spacious 4 bedroom and 3 bath townhouse offers a

22 Photos

50 Trott Boulevard, Simcoe, ON , MLS #S12547164 , Image - 1

50 Trott Boulevard Collingwood, Simcoe, ON MLS® S12547164

Residential Freehold (Detached)

$2700.0

2 Beds
1 Baths
1100-1500 sq-ft

Season rental Winter or Summer. Recently renovated 1200 sf. separate, self contained turn key 2 bedroom suite, fully furnished bnb. Fully equipped kit

32 Photos

12 MITCHELL Avenue, Simcoe, ON , MLS #S12406822 , Image - 1

12 MITCHELL Avenue Collingwood, Simcoe, ON MLS® S12406822

Residential Freehold (Detached)

$3000.0

3 Beds
3 Baths
1100-1500 sq-ft

This modern yet cozy open-concept home of over 1,300 sq ft has everything you need! An open foyer lets light in on both levels and a grey-stained oak

28 Photos

100 Fairway Crescent, Simcoe, ON , MLS #S12525302 , Image - 1

Unit-5, 100 Fairway Crescent Collingwood, Simcoe, ON MLS® S12525302

Residential Condo & Other (Condo Townhouse)

$2550.0

3 Beds
2 Baths
1200-1399 sq-ft

Annual, rental, partially furnished, can provide unfurnished if required. Welcome to 100 Fairway unit 5 in Living Stone Resort, formerly Cranberry Res

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637 Hurontario Street, Simcoe, ON , MLS #S11998853 , Image - 1

Unit-106, 637 Hurontario Street Collingwood, Simcoe, ON MLS® S11998853

Residential Freehold (Store W Apartment/Office)

$2500.0

Reduced by 10.7%

2 Beds
1 Baths
700-1100 sq-ft

Step into a world of historic elegance and contemporary comfort with this unique annual rental, perfectly situated in a meticulouslyrestored historica

26 Photos

1 Brandy Lane Drive, Simcoe, ON , MLS #S12453102 , Image - 1

Unit-104, 1 Brandy Lane Drive Collingwood, Simcoe, ON MLS® S12453102

Residential Condo & Other (Condo Apartment)

$2150.0

2 Beds
2 Baths
800-899 sq-ft

Available for one year rental. Can consider shorter period.This lovely ground level unit has 2 bedrooms. Master bedroom has a queen size bed and ensui

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32 Green Briar Drive, Simcoe, ON , MLS #S12231202 , Image - 1

Unit-32, 32 Green Briar Drive Collingwood, Simcoe, ON MLS® S12231202

Residential Condo & Other (Condo Townhouse)

$18000.0

Reduced by 10.0%

3 +1 Beds
4 Baths
1400-1599 sq-ft

SEASONAL SKI SEASON LEASE FROM MID DECEMBER - END OF MARCH Meticulous Bungalow Located in the Prestigious Briarwood Community. The location can't be b

18 Photos

65B St Vincent Street, Simcoe, ON , MLS #40752602 , Image - 1

65B St Vincent Street Collingwood, Simcoe, ON MLS® 40752602

Residential Lease (Single Family Residence)

$3200

5 Beds
4 Baths
3424 sq-ft

Welcome to 65B St Vincent, a stunning custom-built modern home offering over 2700 sq ft of beautifully finished living space in the heart of Collingwo

31 Photos

291 Mariners Way, Simcoe, ON , MLS #40752949 , Image - 1

291 Mariners Way Collingwood, Simcoe, ON MLS® 40752949

Residential Lease (Row/Townhouse)

$2450

2 Beds
2 Baths
867 sq-ft

SEASONAL RENTAL available in the exclusive waterfront community of Lighthouse Point in Collingwood. This fully furnished unit features two large bedro

31 Photos

67 Maidens Crescent, Simcoe, ON , MLS #40746616 , Image - 1

67 Maidens Crescent Collingwood, Simcoe, ON MLS® 40746616

Residential Lease (Single Family Residence)

$3300

5 Beds
4 Baths
2600 sq-ft

STUNNING 2 STOREY HOME IN SUMMIT VIEW COMMUNITY. CLYDESDALE MODEL WITH 2600 SQFT. 9'CEILING, OPEN CONCEPT. 5 BEDROOMS, 3.1 BATHROOM. SORRING FOYER LEA

28 Photos

70 Shipley Avenue, Simcoe, ON , MLS #40715540 , Image - 1

70 Shipley Avenue Collingwood, Simcoe, ON MLS® 40715540

Residential Lease (Single Family Residence)

$3800

Reduced by 6.2%

5 Beds
4 Baths
2600 sq-ft

STUNNING 2 STOREY HOME IN SUMMIT VIEW COMMUNITY. CLYDESDAL MODEL WITH 2600 SQFT. 9'CEILING, OPEN CONCEPT. 5 BEDROOMS, 3.1 BATHROOM. SORRING FOYER LEAD

25 Photos

234 Simcoe Street, Simcoe, ON , MLS #40681725 , Image - 1

234 Simcoe Street Collingwood, Simcoe, ON MLS® 40681725

Residential Lease (Single Family Residence)

$2500

3 Beds
2 Baths
1200 sq-ft

3 bed, 1.5 bath annual rental located close to Downtown Collingwood. Large rooms throughout including the spacious kitchen with room for a dining tabl

47 Photos

4 Kimberly Lane

Unit-318, 4 Kimberly Lane Collingwood, Simcoe, ON MLS® 40681285

Residential Lease (Condo/Apartment Unit)

$2500

2 Beds
2 Baths
1250 sq-ft

UNFURNISHED ANNUAL RENTAL - Introducing 4 Kimberly Lane #318, an elegant 2 bed + den, 2 bath condo situated in the highly sought-after and brand new R

39 Photos

5 Spooner Crescent, Simcoe, ON , MLS #40673307 , Image - 1

Unit-412, 5 Spooner Crescent Collingwood, Simcoe, ON MLS® 40673307

Residential Lease (Condo/Apartment Unit)

$2600

2 Beds
2 Baths
887 sq-ft

Welcome to Collingwood's newest Condo building located in the wonderful community of BlueFairway. This brand new 2 bedroom condo is located on the top

41 Photos

410 Mariners Way, Simcoe, ON , MLS #40679716 , Image - 1

410 Mariners Way Collingwood, Simcoe, ON MLS® 40679716

Residential Lease (Row/Townhouse)

$3200

3 Beds
2 Baths
1324 sq-ft

Gorgeous Lighthouse Point Annual Lease available December 1, 2024. You do not want to miss this stunning condo that is fully renovated and beautifully

25 Photos

674 Johnston Park Avenue, Simcoe, ON , MLS #40650428 , Image - 1

674 Johnston Park Avenue Collingwood, Simcoe, ON MLS® 40650428

Residential Lease (Condo/Apartment Unit)

$8000

Reduced by 33.3%

2 Beds
2 Baths
870 sq-ft

Seasonal winter rental in Lighthouse Point. Price based on 4 mths with flexible dates. Stunning, newly renovated 2 bed, 2 bath, ground floor unit, boa

30 Photos

394 Fourth Street W, Simcoe, ON , MLS #40642430 , Image - 1

394 Fourth Street W Collingwood, Simcoe, ON MLS® 40642430

Residential Lease (Single Family Residence)

$3200

3 Beds
2 Baths
1298 sq-ft

Welcome to your ideal winter retreat in Collingwood, complete with a relaxing sauna!This beautifully furnished home is perfect for those seeking a sea

17 Photos

594 Oak Street, Simcoe, ON , MLS #40659676 , Image - 1

594 Oak Street Collingwood, Simcoe, ON MLS® 40659676

Residential Lease (Single Family Residence)

$2800

Reduced by 6.7%

4 Beds
2 Baths
1723 sq-ft

***SEASONAL LEASE***Welcome to 594 Oak Street! This charming home is the perfect retreat for a large family looking for a cozy, in-town ski residence.

32 Photos

333 Mariners Way, Simcoe, ON , MLS #40673417 , Image - 1

333 Mariners Way Collingwood, Simcoe, ON MLS® 40673417

Residential Lease (Condo/Apartment Unit)

$3700

3 Beds
2 Baths
1038 sq-ft

Welcome to Lighthouse Point! This 3 bedroom, 2 bathroom condo is on the waterside of Collingwood, 5 minute drive to the ski slopes and Village of Blue

19 Photos

4 Mitchell Avenue, Simcoe, ON , MLS #40679308 , Image - 1

4 Mitchell Avenue Collingwood, Simcoe, ON MLS® 40679308

Residential Lease (Single Family Residence)

$3000

4 Beds
3 Baths
1940 sq-ft

Experience spacious living with this stunning 4-bedroom, 2.5-bathroom Hampton model in Collingwood, available for annual lease. Boasting 1,940 sq. ft.

23 Photos

347 Mariners Way, Simcoe, ON , MLS #40661670 , Image - 1

347 Mariners Way Collingwood, Simcoe, ON MLS® 40661670

Residential Lease (Condo/Apartment Unit)

$7500

2 Beds
2 Baths
1042 sq-ft

SKI SEASON RENTAL, list price is for Dec. 1/24 thru March 31/25 but dates may be flexible. Welcome to beautiful Lighthouse Point, perfectly located mi

19 Photos

22 Ramblings Way, Simcoe, ON , MLS #40671453 , Image - 1

Unit-59, 22 Ramblings Way Collingwood, Simcoe, ON MLS® 40671453

Residential Lease (Condo/Apartment Unit)

$9000

3 Beds
2 Baths
1375 sq-ft

SKI SEASON RENTAL -Welcome to your perfect retreat on the outskirts of Collingwood! This beautifully updated, ground-floor condo features 3 spacious b

32 Photos

349 Mariners Way, Simcoe, ON , MLS #40669696 , Image - 1

349 Mariners Way Collingwood, Simcoe, ON MLS® 40669696

Residential Lease (Condo/Apartment Unit)

$8800

3 Beds
3 Baths
1300 sq-ft

Ski season rental - 3 bdrm, 2.5 bath top floor unit condo at Lighthouse Point, fully furnished and equipped in west Collingwood, sleeps 6, list price

24 Photos

18 Ramblings Way, Simcoe, ON , MLS #40647047 , Image - 1

Unit-92, 18 Ramblings Way Collingwood, Simcoe, ON MLS® 40647047

Residential Lease (Condo/Apartment Unit)

$10500

Reduced by 8.7%

3 Beds
3 Baths
1479 sq-ft

Seasonal Ski Rental Available! Dates are flexible from December to March. This beautiful 3 Bedroom 2.5 Bath Condo in the popular Rupert's Landing Reso

23 Photos

3 Brandy Lane Drive, Simcoe, ON , MLS #40657707 , Image - 1

Unit-302, 3 Brandy Lane Drive Collingwood, Simcoe, ON MLS® 40657707

Residential Lease (Condo/Apartment Unit)

$9250

Reduced by 28.8%

3 Beds
3 Baths
1205 sq-ft

Seasonal Winter Rental in Wyldewood Collingwood! Three bedroom Balsam Wood model has been modified to add a main floor powder room, totaling 3 baths.

26 Photos

5 Anchorage Crescent, Simcoe, ON , MLS #40617541 , Image - 1

Unit-205, 5 Anchorage Crescent Collingwood, Simcoe, ON MLS® 40617541

Residential Lease (Condo/Apartment Unit)

$2100

2 Beds
2 Baths
863 sq-ft

SEASONAL RENTAL Lovely 2 bedroom, 2 bathroom Wyldewood Cove condo. Enjoy the water views from the balcony, take a swim in the heated outdoor pool that

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