Skip to main content
squareyards-logo
Sell Your Home
Shortlisted Properties
  • New Homes
  • For Sale
  • For Rent
Danger! Indicates a dangerous or potentially negative action.
Error

Maximum 4 project can be compared at one go.

L9Y Houses For Lease Under 5K - P2

Showing results 31 - 60 of 102
Last Updated: October 01, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
  • Square Feet(Lo-Hi)
  • Square Feet(Hi-Lo)
31 Photos
Last Updated : 6 Days ago
46 Glen Road, Simcoe, ON , MLS #S13827312 , Image - 1
Image With Blur overlay

Like What you see?

46 Glen Road Collingwood, Simcoe, ON MLS® S13827312

Residential Freehold (Detached)

$3500.0
  • 4 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Location, Location, Perfect House For The Family . 4 Bedroom, two full bathrooms, 2 Car garage, two driveways with 10 car parking, walk to 50 metres t
17 Photos
Last Updated : 7 Days ago
25 Maidens Crescent, Simcoe, ON , MLS #S13824050 , Image - 1

Like What you see?

25 Maidens Crescent Collingwood, Simcoe, ON MLS® S13824050

Residential Freehold (Detached)

$3500.0
  • 4 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome to 25 MAIDENS CRESCENT, Collingwood, Ontario, a beautifully maintained 4-bedroom, 4-bathroom detached home offering over 2,600 sq. ft. of fini
12 Photos
Last Updated : 7 Days ago
11 Harbour Street W, Simcoe, ON , MLS #S13823400 , Image - 1

Like What you see?

Unit-345, 11 Harbour Street W Collingwood, Simcoe, ON MLS® S13823400

Residential Condo & Other (Condo Townhouse)

$2500.0
  • 2 Beds
  • 1 Baths
  • 800-899 sq-ft
Enjoy a cozy winter getaway in this fully furnished, turnkey condo in a quiet Collingwood enclave. Available for a ski season lease, this reverse-layo
18 Photos
Last Updated : 7 Days ago
51 Trott Boulevard, Simcoe, ON , MLS #S13819638 , Image - 1

Like What you see?

Unit-164, 51 Trott Boulevard Collingwood, Simcoe, ON MLS® S13819638

Residential Condo & Other (Condo Apartment)

$2300.0
  • 2 Beds
  • 2 Baths
  • 900-999 sq-ft
Your Collingwood lifestyle starts here! This bright and inviting corner unit at 51 Trott Boulevard offers 2 bedrooms, 2 full bathrooms and a comfortab
30 Photos
Last Updated : 7 Days ago
1 Shipyard Lane, Simcoe, ON , MLS #S13822228 , Image - 1

Like What you see?

1 Shipyard Lane
Unit-303, 1 Shipyard Lane Collingwood, Simcoe, ON MLS® S13822228

Residential Condo & Other (Condo Apartment)

$3000.0
  • 1 +0 Beds
  • 2 Baths
  • 1000-1199 sq-ft
SKI SEASON RENTAL OR ANNUAL LEASE. Rare Opportunity: Reimagined Luxury Penthouse in The Shipyards!Welcome to The FOUNDRY in the highly sought-after Si
15 Photos
Last Updated : 8 Days ago
25 Marina Crescent, Simcoe, ON , MLS #S13809722 , Image - 1

Like What you see?

25 Marina Crescent Collingwood, Simcoe, ON MLS® S13809722

Residential Freehold (Detached)

$4000.0
  • 3 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Spend the heart of ski season in a comfortable, fully furnished family home in Collingwood. Available for a three-month lease from February through Ap
36 Photos
Last Updated : 8 Days ago
183 ALTA Road, Grey County, ON , MLS #X13558596 , Image - 1

Like What you see?

Unit-GROUND LEVEL, 183 ALTA Road Blue Mountains, Grey County, ON MLS® X13558596

Residential Freehold (Detached)

$3899.0
  • 1 Beds
  • 1 Baths
  • 2500-3000 sq-ft
SEASONAL RENTAL GROUND FLOOR UNIT. The ground floor unit can be leased monthly for 3,899 throughout the year or for a season, start dates flexible. S
28 Photos
Last Updated : 8 Days ago
570 OXBOW Crescent, Simcoe, ON , MLS #S13817390 , Image - 1

Like What you see?

570 OXBOW Crescent Collingwood, Simcoe, ON MLS® S13817390

Residential Condo & Other (Condo Townhouse)

$4200.0
  • 4 +0 Beds
  • 3 Baths
  • 1600-1799 sq-ft
WINTER SEASONAL RENTAL! This spacious, beautifully updated, four bedroom, two and half bath condo with postcard views of the mountain is the ideal pla
18 Photos
Last Updated : 9 Days ago
4 Kimberly Lane E, Simcoe, ON , MLS #S13816502 , Image - 1

Like What you see?

Unit-327, 4 Kimberly Lane E Collingwood, Simcoe, ON MLS® S13816502

Residential Condo & Other (Condo Apartment)

$2250.0
  • 1 +1 Beds
  • 1 Baths
  • 700-799 sq-ft
Welcome to refined adult living at Royal Windsor at Balmoral Village in Collingwood. This beautifully upgraded and freshly painted Viscount Model offe
38 Photos
Last Updated : 9 Days ago
184 Stoneleigh Drive, Grey County, ON , MLS #X13756532 , Image - 1

Like What you see?

184 Stoneleigh Drive Blue Mountains, Grey County, ON MLS® X13756532

Residential Freehold (Semi-Detached )

$3000.0
price drop iconReduced by 14.3%
  • 5 Beds
  • 5 Baths
  • 1500-2000 sq-ft
Welcome to contemporary living in Blue Mountain, Ontario. These fresh, modern semi-detached homes offer an exceptional combination of style, space and
46 Photos
Last Updated : 9 Days ago
104 Kinsey Place, Grey County, ON , MLS #X13783988 , Image - 1

Like What you see?

104 Kinsey Place Blue Mountains, Grey County, ON MLS® X13783988

Residential Freehold (Detached)

$4000.0
  • 2 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Fall & Winter Seasonal Rental in the Heart of Blue Mountain - Steps to South Base Lodge & Village! Experience the best of fall and winter in Blue Mou
44 Photos
Last Updated : 10 Days ago
24 Ramblings Way, Simcoe, ON , MLS #S13802736 , Image - 1

Like What you see?

24 Ramblings Way
Unit-905, 24 Ramblings Way Collingwood, Simcoe, ON MLS® S13802736

Residential Condo & Other (Condo Apartment)

$3200.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
5-STAR FULLY FURNISHED RENTAL | 2 BED | 2 BATH | GEORGIAN BAY & BLUE MOUNTAIN VIEWSWelcome to this exceptional fully furnished 2-bedroom, 2-bathroom c
30 Photos
Last Updated : 10 Days ago
49 Trott Boulevard, Simcoe, ON , MLS #S13808400 , Image - 1

Like What you see?

Unit-179, 49 Trott Boulevard Collingwood, Simcoe, ON MLS® S13808400

Residential Condo & Other (Condo Townhouse)

$2650.0
  • 2 Beds
  • 2 Baths
  • 900-999 sq-ft
Welcome to Harbourside 1 in Collingwood. Furnished, short term rental, 2-4 months, $2,650 per month including utilities. Bungalow style condo townhous
36 Photos
Last Updated : 10 Days ago
15 Dawson Drive, Simcoe, ON , MLS #S13617060 , Image - 1

Like What you see?

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

Residential Condo & Other (Condo Townhouse)

$2050.0
price drop iconReduced by 6.8%
  • 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
19 Photos
Last Updated : 12 Days ago
22 St. Paul Street, Simcoe, ON , MLS #S13793212 , Image - 1

Like What you see?

22 St. Paul Street Collingwood, Simcoe, ON MLS® S13793212

Residential Freehold (Semi-Detached )

$2700.0
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
This modern, rustic farmhouse has been beautifully renovated while maintaining the vintage charm of the home of Collingwoods original Harbour Master.
9 Photos
Last Updated : 13 Days ago
19 Dawson Drive, Simcoe, ON , MLS #S13679748 , Image - 1

Like What you see?

Unit-64, 19 Dawson Drive Collingwood, Simcoe, ON MLS® S13679748

Residential Condo & Other (Condo Apartment)

$1950.0
price drop iconReduced by 7.1%
  • 2 Beds
  • 2 Baths
  • 700-799 sq-ft
ANNUAL LEASE -- Welcome to Unit 64 at 19 Dawson Drive. Tucked away in a desirable Collingwood community, this beautifully updated ground-floor condo o
12 Photos
Last Updated : 13 Days ago
218 Fifth Street, Simcoe, ON , MLS #S13786926 , Image - 1

Like What you see?

Unit-2, 218 Fifth Street Collingwood, Simcoe, ON MLS® S13786926

Residential Freehold (Duplex)

$2750.0
  • 2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Collingwood Duplex with 2 separate apartments for rent: Unit 2 is unfurnished and being offered for annual rental at a monthly rent of $2750 (Utilitie
25 Photos
Last Updated : 13 Days ago
7 Willow Street, Simcoe, ON , MLS #S13801000 , Image - 1

Like What you see?

7 Willow Street Collingwood, Simcoe, ON MLS® S13801000

Residential Freehold (Detached)

$1900.0
  • 2 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Settle into Collingwood living with this bright and welcoming two-bedroom lower-level apartment, offering comfortable everyday living in a peaceful re
7 Photos
Last Updated : 14 Days ago
176 Eighth Street, Simcoe, ON , MLS #S13780494 , Image - 1

Like What you see?

Unit-201, 176 Eighth Street Collingwood, Simcoe, ON MLS® S13780494

Residential Condo & Other (Condo Apartment)

$2000.0
  • 2 Beds
  • 1 Baths
  • 800-899 sq-ft
ANNUAL LEASE AVAILABLE IMMEDIATELY. Bright and spacious upper-level two-bedroom, one-bath unit ideally located in the heart of Collingwood. Just steps
40 Photos
Last Updated : 14 Days ago
28 TESKEY Court, Simcoe, ON , MLS #S13797094 , Image - 1

Like What you see?

28 TESKEY Court Collingwood, Simcoe, ON MLS® S13797094

Residential Freehold (Detached)

$3000.0
  • 2 +1 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Welcome to 28 Teskey Court in Collingwood! Step inside this beautifully renovated raised bungalow, where comfortable living meets thoughtful updates.
43 Photos
Last Updated : 14 Days ago
171 Snowbridge Way, Grey County, ON , MLS #X13726994 , Image - 1

Like What you see?

Unit-24, 171 Snowbridge Way Blue Mountains, Grey County, ON MLS® X13726994

Residential Condo & Other (Condo Townhouse)

$2800.0
  • 3 +0 Beds
  • 4 Baths
  • 1800-1999 sq-ft
Blue Mountain seasonal rental in sought-after Snowbridge! Available for both a fall getaway or the full 4-month ski season. This spacious, fully furni
38 Photos
Last Updated : 14 Days ago
31 Huron Street, Simcoe, ON , MLS #S13793794 , Image - 1

Like What you see?

Unit-618, 31 Huron Street Collingwood, Simcoe, ON MLS® S13793794

Residential Condo & Other (Condo Apartment)

$3700.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Welcome to Penthouse 618 at Harbour House, Collingwood's premier waterfront condominium in the heart of downtown. Completed in 2025, this luxury resid
24 Photos
Last Updated : 15 Days ago
56 Winters Crescent, Simcoe, ON , MLS #S13790324 , Image - 1

Like What you see?

56 Winters Crescent Collingwood, Simcoe, ON MLS® S13790324

Residential Condo & Other (Condo Townhouse)

$2500.0
  • 2 Beds
  • 3 Baths
  • 1400-1599 sq-ft
**ANNUAL UNFURNISHED LEASE** Embrace Modern Living: Newly Constructed Three-Story Townhome Ready for You! Nestled in the Tranquil West End of Collingw
11 Photos
Last Updated : 15 Days ago
642 Oak Street, Simcoe, ON , MLS #S13791386 , Image - 1

Like What you see?

642 Oak Street Collingwood, Simcoe, ON MLS® S13791386

Residential Freehold (Detached)

$2300.0
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Newly Renovated Main Floor Annual Rental in Central Collingwood. Welcome to 642 Oak Street. This thoughtfully renovated main-floor residence offers a
22 Photos
Last Updated : 15 Days ago
590 Tenth Street, Simcoe, ON , MLS #S13780960 , Image - 1

Like What you see?

590 Tenth Street Collingwood, Simcoe, ON MLS® S13780960

Residential Condo & Other (Condo Townhouse)

$2300.0
  • 3 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Annual rental with flexible dates, as early as Oct 1st. Townhouse style condo with it's own yard in the heart of Collingwood. An open concept main flo
40 Photos
Last Updated : 15 Days ago
774 Johnston Park Avenue, Simcoe, ON , MLS #S13787888 , Image - 1

Like What you see?

774 Johnston Park Avenue Collingwood, Simcoe, ON MLS® S13787888

Residential Condo & Other (Condo Townhouse)

$4000.0
  • 4 Beds
  • 3 Baths
  • 1600-1799 sq-ft
This spacious, Orchid Garden Home with an attached Garage, Updated Designer Kitchen and Baths with Quartz counter tops and designer glass showers, is
40 Photos
Last Updated : 15 Days ago
109 Archer Avenue, Simcoe, ON , MLS #S13789864 , Image - 1

Like What you see?

109 Archer Avenue Collingwood, Simcoe, ON MLS® S13789864

Residential Freehold (Att/Row/Townhouse)

$2550.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to this beautiful brand-new semi-detached home in Collingwood, offering the perfect combination of modern comfort, family-friendly living and
24 Photos
Last Updated : 15 Days ago
9 Trafalgar Road, Simcoe, ON , MLS #S13789428 , Image - 1

Like What you see?

9 Trafalgar Road Collingwood, Simcoe, ON MLS® S13789428

Residential Condo & Other (Condo Townhouse)

$3000.0
  • 3 Beds
  • 3 Baths
  • 1400-1599 sq-ft
Fall & Winter Seasonal Rental in Whisper Woods, Collingwood. Enjoy a peaceful fall and winter getaway in this beautifully updated 3-bedroom, 3-bathroo
9 Photos
Last Updated : 16 Days ago
3 Portland St Street, Simcoe, ON , MLS #S13712282 , Image - 1

Like What you see?

3 Portland St Street Collingwood, Simcoe, ON MLS® S13712282

Residential Freehold (Lower Level)

$1875.0
price drop iconReduced by 5.1%
  • 1 Beds
  • 1 Baths
  • < 700 sq-ft
Extra large bright 1 bedroom basement apartment with separate entrance in Collingwood's popular South end. Easy access off Poplar Sideroad and minutes
29 Photos
Last Updated : 17 Days ago
826 SUNCREST Circle, Simcoe, ON , MLS #S13767936 , Image - 1

Like What you see?

826 SUNCREST Circle Collingwood, Simcoe, ON MLS® S13767936

Residential Condo & Other (Condo Townhouse)

$3000.0
  • 3 +0 Beds
  • 3 Baths
  • 1200-1399 sq-ft
SKI-SEASON LEASE IN LIGHTHOUSE POINT! Flexible dates. This spacious and stylish townhome style condo offers an open concept main floor, snapshot views
Shortlisted Properties
error icon
Error

Maximum 4 project can be compared at one go.

Tell us a Little about yourself!