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Houses for Rent in Collingwood ON Under $500K

Showing results 1 - 30 of 79

Check out our extensive selection of houses under $500k for rent in Collingwood on Square Yards Canada. With over 79 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: August 06, 2026

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31 SLALOM GATE Road, Simcoe, ON , MLS #S13640614 , Image - 1

31 SLALOM GATE Road Collingwood, Simcoe, ON MLS® S13640614

Residential Freehold (Detached)

$4000.0

1 +2 Beds
2 Baths
1500-2000 sq-ft

Luxurious Seasonal Rental with a massive lot that backs onto the Silver Creek. Available immediately through to November 2026. This fully renovated an

37 Photos

32 Courtice Crescent, Simcoe, ON , MLS #S13643282 , Image - 1

32 Courtice Crescent Collingwood, Simcoe, ON MLS® S13643282

Residential Freehold (Detached)

$2900.0

3 +0 Beds
2 Baths
700-1100 sq-ft

Available for Seasonal, Monthly or Annual rental with potential to be partially furnished as well. This family home on a large fully fenced lot with g

21 Photos

32 JOSEPH Trail, Simcoe, ON , MLS #S13581776 , Image - 1

32 JOSEPH Trail Collingwood, Simcoe, ON MLS® S13581776

Residential Condo & Other (Condo Townhouse)

$2450.0

2 +0 Beds
2 Baths
1000-1199 sq-ft

FALL AND SKI SEASON RENTALS AVAILABLE. Located in the quiet Tanglewood neighbourhood, less than a 10-minute drive to Blue Mountain Village and 5 minut

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149 Fairway Crescent, Simcoe, ON , MLS #S13594736 , Image - 1

Unit-71, 149 Fairway Crescent Collingwood, Simcoe, ON MLS® S13594736

Residential Condo & Other (Condo Townhouse)

$2225.0

2 Beds
2 Baths
900-999 sq-ft

FURNISHED - SEASONAL LEASE. Available now until the end of NOV.. Make this your home away from home for a season! Welcome to Unit 71 at 149 Fairway Cr

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66 Portland Street, Simcoe, ON , MLS #S13642102 , Image - 1

66 Portland Street Collingwood, Simcoe, ON MLS® S13642102

Residential Freehold (Detached)

$3500.0

4 Beds
3 Baths
2500-3000 sq-ft

Discover the ultimate lifestyle with this exclusive leasing opportunity! Immerse yourself in the charm of a stunning detached home, just moments away

35 Photos

26 Barrington Trail N/A, Simcoe, ON , MLS #S13640764 , Image - 1

26 Barrington Trail N/A Collingwood, Simcoe, ON MLS® S13640764

Residential Freehold (Detached)

$3200.0

3 Beds
3 Baths
1500-2000 sq-ft

Top 5 Reasons You Will Love This Home: 1) Welcome to the 'Cameron Model' by Eden Oaks, available for lease immediately, ideally located just steps fro

40 Photos

37 Georgian Manor Drive, Simcoe, ON , MLS #S13639618 , Image - 1

37 Georgian Manor Drive Collingwood, Simcoe, ON MLS® S13639618

Residential Freehold (Detached)

$6000.0

4 +1 Beds
3 Baths
1500-2000 sq-ft

Discover the ultimate year-round, four season gem - a spacious, fully furnished waterfront getaway nestled in a peaceful, serene, private wooded setti

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30 Pine Street, Simcoe, ON , MLS #S13636318 , Image - 1

Unit-Unit 2, 30 Pine Street Collingwood, Simcoe, ON MLS® S13636318

Residential Freehold (Upper Level)

$2450.0

2 Beds
1 Baths
700-1100 sq-ft

Annual Residential Lease in Downtown Collingwood, in an attractive Heritage Home in the Heritage Conservation District! This newly renovated 2 bedroom

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2 Golfview Drive, Simcoe, ON , MLS #S12756574 , Image - 1

Unit-1, 2 Golfview Drive Collingwood, Simcoe, ON MLS® S12756574

Residential Freehold (Att/Row/Townhouse)

$2425.0

Reduced by 1.0%

2 Beds
2 Baths
700-1100 sq-ft

Annual Rental - $2,450/month plus utilities. Available April 1st. Pictures to come. Be the first to live in this brand new(2026) 2-bedroom, 2-bath sui

24 Photos

149 Fairway Crescent, Simcoe, ON , MLS #S13223868 , Image - 1

Unit-73, 149 Fairway Crescent Collingwood, Simcoe, ON MLS® S13223868

Residential Condo & Other (Condo Townhouse)

$2250.0

2 Beds
2 Baths
1000-1199 sq-ft

***Available for September & October*** Welcome to this bright and inviting end-unit condo in the sought-after Living Stone community (formerly Cranb

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44 Trott Boulevard, Simcoe, ON , MLS #S13634516 , Image - 1

Unit-13, 44 Trott Boulevard Collingwood, Simcoe, ON MLS® S13634516

Residential Condo & Other (Condo Townhouse)

$2600.0

3 +0 Beds
2 Baths
1200-1399 sq-ft

ANNUAL FURNISHED RENTAL, AVAILABLE SEPTEMBER 1ST. Enjoy effortless year-round living in this beautifully furnished 3-bedroom, 2-bathroom ground-floor

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2 Anchorage Crescent W, Simcoe, ON , MLS #S13620378 , Image - 1

Unit-308, 2 Anchorage Crescent W Collingwood, Simcoe, ON MLS® S13620378

Residential Condo & Other (Condo Apartment)

$1900.0

1 Beds
1 Baths
700-799 sq-ft

Seasonal rental available for Summer, Fall & Ski seasons! Fully Furnished, in Popular Wyldewood Cove 1 Bedroom, 1 Bath Condo, on the shores of Georgia

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29 NORTH MAPLE Street, Simcoe, ON , MLS #S13613504 , Image - 1

29 NORTH MAPLE Street Collingwood, Simcoe, ON MLS® S13613504

Residential Condo & Other (Condo Townhouse)

$18000.0

3 +0 Beds
2 Baths
1600-1799 sq-ft

SHIPYARDS WINTER RENTAL! 3 bedrooms, 2.5 baths, warm furniture and decor - turn key condo ready for your family. Spacious primary bedroom + ensuite, c

25 Photos

23 Archer Avenue, Simcoe, ON , MLS #S13551376 , Image - 1

23 Archer Avenue Collingwood, Simcoe, ON MLS® S13551376

Residential Freehold (Att/Row/Townhouse)

$2800.0

3 Beds
3 Baths
1100-1500 sq-ft

Fully furnished, impeccably maintained, and ready for you to simply move in: this 3-bedroom, 3-bathroom end-unit townhome offers annual lease living i

31 Photos

49 Trott Boulevard, Simcoe, ON , MLS #S13083882 , Image - 1

Unit-193, 49 Trott Boulevard Collingwood, Simcoe, ON MLS® S13083882

Residential Condo & Other (Condo Apartment)

$2350.0

Reduced by 9.6%

3 Beds
2 Baths
1000-1199 sq-ft

Fantastic opportunity to own a 3 bedroom, ground floor, bungalow style condo! All brand new appliances, new quartz countertop, carpet free unit featu

43 Photos

5 Gregory Avenue, Simcoe, ON , MLS #S13465072 , Image - 1

5 Gregory Avenue Collingwood, Simcoe, ON MLS® S13465072

Residential Freehold (Att/Row/Townhouse)

$2550.0

Reduced by 8.9%

3 Beds
3 Baths
1100-1500 sq-ft

Fantastic Opportunity to live in the Heart of Collingwood - Beautiful Freehold Townhome! Welcome to this spacious and well-maintained 3-bedroom, 3-bat

26 Photos

9811 Beachwood Road, Simcoe, ON , MLS #S13629516 , Image - 1

9811 Beachwood Road Collingwood, Simcoe, ON MLS® S13629516

Residential Freehold (Multiplex)

$2200.0

2 Beds
1 Baths
< 700 sq-ft

Welcome to this beautifully renovated 2-bedroom, 1-bathroom apartment offering stylish finishes, modern updates, and an unbeatable Southern Georgian B

36 Photos

15 Dawson Drive, Simcoe, ON , MLS #S13617060 , Image - 1

Unit-6, 15 Dawson Drive Collingwood, Simcoe, ON MLS® S13617060

Residential Condo & Other (Condo Townhouse)

$2200.0

2 Beds
2 Baths
700-799 sq-ft

Short Term and Annual Rental Available in the family friendly Community of Cranberry Resort, close to Georgian Bay. This beautiful 2 Bedroom, 2 Bathro

25 Photos

108 Katherine Street, Simcoe, ON , MLS #S13616948 , Image - 1

108 Katherine Street Collingwood, Simcoe, ON MLS® S13616948

Residential Freehold (Detached)

$2600.0

2 +1 Beds
2 Baths
700-1100 sq-ft

Annual lease in central Collingwood. Charming detached brick side split offering 3 bedrooms, 2 bathrooms, and 1,430 sq ft of finished living space in

37 Photos

31 Huron Street, Simcoe, ON , MLS #S13628870 , Image - 1

Unit-511, 31 Huron Street Collingwood, Simcoe, ON MLS® S13628870

Residential Condo & Other (Condo Apartment)

$2500.0

1 Beds
1 Baths
600-699 sq-ft

Ski Season Rental - 1 Bedroom + Den Condo in Downtown Collingwood. Enjoy the perfect winter getaway in this beautifully appointed 1-bedroom plus den c

32 Photos

4 Anchorage Crescent, Simcoe, ON , MLS #S13605328 , Image - 1

Unit-205, 4 Anchorage Crescent Collingwood, Simcoe, ON MLS® S13605328

Residential Condo & Other (Condo Apartment)

$2100.0

1 +1 Beds
2 Baths
700-799 sq-ft

Furnished Annual Lease available at Wyldewood Cove! This charming One Bedroom, plus den, offers a cozy living space with stylish decor, granite counte

29 Photos

11 HARBOUR Street W, Simcoe, ON , MLS #S13625920 , Image - 1

Unit-341, 11 HARBOUR Street W Collingwood, Simcoe, ON MLS® S13625920

Residential Condo & Other (Condo Townhouse)

$10000.0

2 +0 Beds
2 Baths
1000-1199 sq-ft

SEASONAL 2026/2027 - SKI SEASON RENTAL - Great 2 bedroom, 2 bath bungalow end unit in the desirable Cranberry community with no one above or below you

15 Photos

4 COVE Court, Simcoe, ON , MLS #S13560526 , Image - 1

Unit-104, 4 COVE Court Collingwood, Simcoe, ON MLS® S13560526

Residential Condo & Other (Condo Apartment)

$2000.0

Reduced by 9.1%

1 +0 Beds
1 Baths
800-899 sq-ft

**WINTER SEASONAL RENTAL | FURNISHED 1 BEDROOM + DEN**Enjoy everything winter in Southern Georgian Bay from this beautifully furnished ground-floor co

17 Photos

317 Hume Street, Simcoe, ON , MLS #S13624042 , Image - 1

317 Hume Street Collingwood, Simcoe, ON MLS® S13624042

Residential Freehold (Detached)

$1900.0

3 Beds
1 Baths
1100-1500 sq-ft

Welcome home to this charming 3 bedroom annual rental on Hume Street, ideally located just a short walk to downtown Collingwood, local trails, the YMC

28 Photos

17 Spooner Crescent, Simcoe, ON , MLS #S13448540 , Image - 1

Unit-308, 17 Spooner Crescent Collingwood, Simcoe, ON MLS® S13448540

Residential Condo & Other (Condo Apartment)

$2200.0

2 Beds
2 Baths
800-899 sq-ft

Welcome to this new, bright, and spacious 2-bedroom, 2-bathroom luxury condo in the sought-after The View Blue Fairway, overlooking the picturesque Cr

43 Photos

31 Huron Street, Simcoe, ON , MLS #S13158882 , Image - 1

Unit-405, 31 Huron Street Collingwood, Simcoe, ON MLS® S13158882

Residential Condo & Other (Condo Apartment)

$2895.0

2 Beds
2 Baths
900-999 sq-ft

Experience elevated waterfront living at Harbour House, Collingwood's most coveted new luxury residence. This brand-new, fully upgraded corner suite o

7 Photos

34 Dawson Drive, Simcoe, ON , MLS #S13615730 , Image - 1

Unit-841A, 34 Dawson Drive Collingwood, Simcoe, ON MLS® S13615730

Residential Condo & Other (Condo Townhouse)

$1500.0

1 Baths
500-599 sq-ft

Well-maintained bachelor apartment close to Downtown Collingwood and everything the Blue Mountain has to offer. Featuring an open plan kitchen/living

15 Photos

4 RAMBLINGS Way, Simcoe, ON , MLS #S13621202 , Image - 1

Unit-14, 4 RAMBLINGS Way Collingwood, Simcoe, ON MLS® S13621202

Residential Condo & Other (Condo Apartment)

$10000.0

2 +0 Beds
2 Baths
1000-1199 sq-ft

SEASONAL RENTAL - Available for ski season starting December 1st. Renovated two bedroom, 2 bath ground floor condo in Ruperts Landing. Nicely furnishe

37 Photos

29 St Clair Street, Simcoe, ON , MLS #S13535672 , Image - 1

29 St Clair Street Collingwood, Simcoe, ON MLS® S13535672

Residential Freehold (Detached)

$15000.0

5 Beds
4 Baths
2500-3000 sq-ft

Welcome to The Lake House - a bright & airy 5 bedroom lakeside retreat on the stunning shores of Georgian Bay, with a separate 1 bdrm Coach House. Thi

30 Photos

27 Conservation Way, Simcoe, ON , MLS #S13609436 , Image - 1

27 Conservation Way Collingwood, Simcoe, ON MLS® S13609436

Residential Condo & Other (Condo Townhouse)

$16000.0

3 Beds
4 Baths
1200-1399 sq-ft

Price listed of $16,000 is for ski season from December 1, 2026-March 31, 2027. Also available from September 15, 2026 to April 15, 2027. Located in o

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