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Cheap Houses for Rent in Windermere, FL

25 rentals

8168 Boat Hook Loop #305 - Photo 1 of 1

5d+ ago

Cheap house for rent in Windermere

8168 Boat Hook Loop #305, Windermere, FL 34786

Affordable | Swimming pool

3 beds

2 baths

$2,100

House for rent

8000 Stirrupwood Ct - Photo 1 of 1

2d ago

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Verified

8000 Stirrupwood Ct, Pine Hills, FL 32818

Affordable | Garage parking | Outdoor space

3 beds

2 baths

$3,460

$2,205

Price drop

House for rent

Available Feb 19

Top amenities
Ceiling Fan
Garage Parking
2297 Blake Way - Photo 1 of 1

5d+ ago

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Verified

2297 Blake Way, Ocoee, FL 34761

Affordable | On-site laundry | Garage parking

3 beds

2 baths

$2,240

House for rent

Available Jan 19

Top amenities
Ceiling Fan
Fireplace
On-Site Laundry
8265 Maritime Flag St #101 - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Windermere

Townhouse - WINDERMERE, FL

8265 Maritime Flag St #101, Windermere, FL 34786

Affordable | In-unit laundry | Assigned parking

3 beds

2 baths

$2,300

House for rent

Top amenities
Dishwasher
In-Unit Laundry
Swimming Pool
5589 Remsen Cay Ln - Photo 1 of 1

5d+ ago

Cheap house for rent in Windermere

Single Family Residence - WINDERMERE, FL

5589 Remsen Cay Ln, Windermere, FL 34786

Affordable | In-unit laundry | Garage parking

4 beds

2 baths

$2,340

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
7351 Millstone St - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Windermere

Townhouse - WINDERMERE, FL

7351 Millstone St, Windermere, FL 34786

Affordable | In-unit laundry | Garage parking

3 beds

2 baths

$2,400

House for rent

Top amenities
Ceiling Fan
Dishwasher
In-Unit Laundry
On-Site Laundry

Nearby rental good for eco-living

Nearby rental good for pet owners

$2,960

Ocoee

11909 Cave Run Ave - Photo 1 of 1

5d+ ago

Cheap house for rent in Windermere

11909 Cave Run Ave

11909 Cave Run Ave, Windermere, FL 34786

Affordable | Storage | Outdoor space

4 beds

3 baths

$2,650

House for rent

Available May 16

744 Westcliffe Dr - Photo 1 of 1

2d ago

Our team has verified this company

Verified

744 Westcliffe Dr, Winter Garden, FL 34787

Affordable | Garage parking | Hardwood floor

4 beds

2 baths

$3,035

$2,675

Price drop

House for rent

Available Dec 12

Top amenities
Garage Parking
Hardwood Floor
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7654 Fairgrove Ave - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Windermere

Townhouse - WINDERMERE, FL

7654 Fairgrove Ave, Windermere, FL 34786

Affordable | In-unit laundry | Garage parking

4 beds

2 baths

$2,700

House for rent

Top amenities
Air Conditioning
Garage Parking
In-Unit Laundry
Swimming Pool
2401 Griffin Ct - Photo 1 of 1

5d+ ago

Cheap house for rent in Ocoee

2401 Griffin Ct, Ocoee, FL 34761

Affordable

4 beds

2 baths

$2,800

House for rent

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These rentals are 10%-30% cheaper than the local average price for similar rentals.

$2,100

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$2,300

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$2,650

Windermere

$2,700

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8320 Iron Mountain Trl - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Windermere

8320 Iron Mountain Trl, Windermere, FL 34786

Affordable | In-unit laundry | Dishwasher

4 beds

2 baths

$2,887

House for rent

Top amenities
In-Unit Laundry
Microwave
Swimming Pool
12337 Via Derna Pl - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Windermere

Townhouse - WINDERMERE, FL

12337 Via Derna Pl, Windermere, FL 34786

Affordable | In-unit laundry | Garage parking

4 beds

3 baths

$2,890

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
12647 Arley Dr - Photo 1 of 1

5d+ ago

Cheap house for rent in Windermere

12647 Arley Dr, Windermere, FL 34786

Affordable | Carpet

4 beds

2 baths

$2,900

House for rent

14217 Bridgewater Crossings Blvd - Photo 1 of 1

5d+ ago

Cheap house for rent in Windermere

Single Family Residence - WINDERMERE, FL

14217 Bridgewater Crossings Blvd, Windermere, FL 34786

Affordable | In-unit laundry | Garage parking

4 beds

3 baths

$3,000

House for rent

Top amenities
Ceiling Fan
In-Unit Laundry
10733 Village Lake Road - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Windermere

10733 Village Lake Road, Windermere, FL 34786

Affordable | In-unit laundry | Garage parking

4 beds

3 baths

$3,075

House for rent

Top amenities
In-Unit Laundry
On-Site Laundry
12921 Cragside Ln #1 - Photo 1 of 1

2h ago

Cheap house for rent in Windermere

12921 Cragside Lane - 1

12921 Cragside Ln #1, Windermere, FL 34786

Affordable | On-site laundry | Garage parking

4 beds

2 baths

$3,100

House for rent

Available Nov 1

Top amenities
On-Site Laundry
4835 Blue Major Drive - Photo 1 of 1

5d+ ago

Cheap house for rent in Windermere

4835 Blue Major Drive, Windermere, FL 34786

Affordable

4 beds

3 baths

$3,170

House for rent

11919 Sheltering Pine Drive - Photo 1 of 1

5d+ ago

Cheap house for rent in Orlando

House for rent

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6836 Trellis Vine Loop #NA - Photo 1 of 1

5d+ ago

Cheap house for rent in Windermere

6836 Trellis Vine Loop - N/A

6836 Trellis Vine Loop #NA, Windermere, FL 34786

Affordable

5 beds

3 baths

$3,300

House for rent

Available Nov 15

6836 Trellis Vine Loop - Photo 1 of 1

5d+ ago

Cheap house for rent in Windermere

6836 Trellis Vine Loop, Windermere, FL 34786

Affordable | On-site laundry | Hardwood floor

5 beds

3 baths

$3,300

House for rent

Available Nov 15

Top amenities
On-Site Laundry
12821 Westside Village Loop - Photo 1 of 1

5d+ ago

Cheap house for rent in Windermere

Single Family Residence - WINDERMERE, FL

12821 Westside Village Loop, Windermere, FL 34786

Affordable | In-unit laundry | Garage parking

5 beds

3 baths

$3,800

House for rent

Top amenities
Garage Parking
In-Unit Laundry
8931 Lookout Pointe Dr - Photo 1 of 1
3D tour

5d+ ago

Cheap house for rent in Windermere

8931 Lookout Pointe Dr, Windermere, FL 34786

Affordable | Garage parking | Dishwasher

5 beds

4 baths

$3,949

House for rent

Available Dec 15

Top amenities
Garage Parking
On-Site Management
Package Service
9088 Outlook Rock Trl - Photo 1 of 1

5d+ ago

Cheap house for rent in Windermere

Single Family Residence - WINDERMERE, FL

9088 Outlook Rock Trl, Windermere, FL 34786

Affordable | In-unit laundry | Garage parking

5 beds

4 baths

$3,950

House for rent

Top amenities
Carpet
Garage Parking
In-Unit Laundry
14409 Crest Palm Ave - Photo 1 of 1

5d+ ago

Cheap house for rent in Windermere

14409 Crest Palm Ave, Windermere, FL 34786

Affordable | Dishwasher | Outdoor space

6 beds

3 baths

$4,500

House for rent

14415 Crest Palm Ave - Photo 1 of 1

5d+ ago

Cheap house for rent in Windermere

14415 Crest Palm Ave, Windermere, FL 34786

Affordable | Dishwasher | Outdoor space

6 beds

3 baths

$4,500

House for rent

Showing 1 - 25 of 25 results
Home > House Rentals in Windermere > Windermere Cheap Houses For Rent
Updated: January 8, 2026

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Discover cheap Windermere, FL houses for rent

🌇Available cheap house rentals25 houses
💰Best rent deal8168 Boat Hook Loop #305
⭐Popular amenities, ,
🔌Utilities included
🏠With photos