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Cheap Houses for Rent in Highlands, Winter Springs, FL

25 rentals

181 Garden Dr - Photo 1 of 1

5d+ ago

Cheap North Orlando townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

181 Garden Dr, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

2 beds

1 bath

$1,295

House for rent

Top amenities
Ceiling Fan
In-Unit Laundry
156 Lori Anne Ln - Photo 1 of 1

5d+ ago

Cheap North Orlando townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

156 Lori Anne Ln, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

2 beds

1 bath

$1,350

House for rent

Top amenities
Carpet
In-Unit Laundry
On-Site Laundry
250 Moree Loop #1 - Photo 1 of 1

5d+ ago

Cheap Highlands townhouse for rent in Winter Springs

250 Moree Loop Unit #6 - 1

250 Moree Loop #1, Winter Springs, FL 32708

Affordable | In-unit laundry | Storage

2 beds

1 bath

$1,449

House for rent

Available Sep 17

Top amenities
In-Unit Laundry
209 Sweetgum Court - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

209 Sweetgum Court, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

3 beds

2 baths

$1,555

House for rent

Available Sep 14

Top amenities
Carpet
Hardwood Floor
High Ceilings
In-Unit Laundry
Storage
Wheelchair Accessible
472 Winding Oak Ln - Photo 1 of 1

1d ago

Our team has verified this company

Verified

472 Winding Oak Ln Longwood, FL 32750

472 Winding Oak Ln, Longwood, FL 32750

Affordable | Garage parking | Outdoor space

3 beds

2 baths

$1,899

$1,745

Price drop

House for rent

Available Jun 30

520 Georgia Ave - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

520 Georgia Ave, Longwood, FL 32750

Affordable | On-site management | Swimming pool

4 beds

2 baths

$1,920

$1,785

Price drop

House for rent

Top amenities
On-Site Management

Nearby rental good for eco-living

$1,295

North Orlando

Nearby rental good for pet owners

$1,555

North Orlando

Nearby rental good for social life

$2,075

Winter Springs

429 Sheoah Blvd #12 - Photo 1 of 1

3d ago

Cheap Highlands house for rent in Winter Springs

429 Sheoah Blvd #12, Winter Springs, FL 32708

Affordable | Swimming pool

3 beds

2 baths

$2,100

$1,875

Price drop

House for rent

135 Cortez Ct - Photo 1 of 1

5d+ ago

Cheap North Orlando house for rent in Winter Springs

135 Cortez Ct, Winter Springs, FL 32708

Affordable

3 beds

2 baths

$1,970

House for rent

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647 Redwood Dr - Photo 1 of 1

23h ago

Our team has verified this company

Verified

647 Redwood Dr, Winter Springs, FL 32708

Affordable

3 beds

2 baths

$1,995

House for rent

Available Nov 21

309 San Gabriel St - Photo 1 of 1

4h ago

Cheap house for rent in Winter Springs

Single Family Residence - WINTER SPRINGS, FL

309 San Gabriel St, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

3 beds

2 baths

$1,995

House for rent

Top amenities
Ceiling Fan
Dishwasher
In-Unit Laundry
Storage
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Find sweet deals near Highlands

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

$1,875

Highlands

$2,000

Highlands

$1,995

Winter Springs

$1,555

North Orlando

474 Club Dr - Photo 1 of 1

5d+ ago

Cheap Highlands townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

474 Club Dr, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

3 beds

2 baths

$2,200

$2,000

Price drop

House for rent

Top amenities
Carpet
Dishwasher
In-Unit Laundry
Swimming Pool
914 Osceola Trl - Photo 1 of 1

5d+ ago

Cheap house for rent in Casselberry

914 Osceola Trl, Casselberry, FL 32707

Affordable | On-site laundry | Assigned parking

3 beds

2 baths

$2,000

House for rent

Top amenities
Air Conditioning
Ceiling Fan
Central Heat
On-Site Laundry
213 Sweetgum Ct - Photo 1 of 1

4d ago

Our team has verified this company

Verified

213 Sweetgum Ct Winter Springs, FL 32708

213 Sweetgum Ct, Winter Springs, FL 32708

Affordable | Garage parking | Outdoor space

3 beds

2 baths

$2,075

House for rent

Available Sep 10

705 Woodlawn Dr - Photo 1 of 1
Rent special

5d+ ago

Cheap house for rent in Winter Springs

3 Bedroom Pet-Friendly Home in Winter Springs, FL with Main Street Renewal

705 Woodlawn Dr, Winter Springs, FL 32708

Affordable | Storage | Outdoor space

3 beds

2 baths

$2,175

$2,075

Price drop

House for rent

670 Macduff Ln #A - Photo 1 of 1

5d+ ago

Cheap Highlands townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

670 Macduff Ln #A, Winter Springs, FL 32708

Affordable | In-unit laundry | Garage parking

3 beds

2 baths

$2,150

House for rent

Top amenities
Dishwasher
High Ceilings
In-Unit Laundry
Swimming Pool
633 Alton Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

633 Alton Rd Winter Springs, FL 32708

633 Alton Rd, Winter Springs, FL 32708

Affordable | Garage parking | Outdoor space

3 beds

2 baths

$2,299

$2,175

Price drop

House for rent

Available Aug 29

403 Cidermill Pl - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

403 Cidermill Pl Lake Mary, FL 32746

403 Cidermill Pl, Lake Mary, FL 32746

Affordable | Garage parking | Outdoor space

3 beds

2 baths

$2,325

$2,190

Price drop

House for rent

Available Sep 10

Top amenities
Fireplace
452 Harbor Winds Ct - Photo 1 of 1

5d+ ago

Cheap Highlands townhouse for rent in Winter Springs

Townhouse - Winter Springs, FL

452 Harbor Winds Ct, Winter Springs, FL 32708

Affordable | In-unit laundry | Garage parking

3 beds

2 baths

$2,200

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
On-Site Laundry
Storage
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424 Club Dr - Photo 1 of 1

5d+ ago

Cheap Highlands townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

424 Club Dr, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

3 beds

2 baths

$2,200

House for rent

Top amenities
Dishwasher
In-Unit Laundry
Swimming Pool
302 Bridie Ct - Photo 1 of 1

5d+ ago

Cheap Highlands house for rent in Winter Springs

302 Bridie Ct, Winter Springs, FL 32708

Affordable | Swimming pool | Residents lounge

3 beds

2 baths

$2,450

House for rent

1260 Seminola Boulevard - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1260 Seminola Boulevard, Casselberry, FL 32707

Affordable | In-unit laundry | Dishwasher

3 beds

2 baths

$2,600

House for rent

Available Sep 11

Top amenities
Air Conditioning
Dishwasher
In-Unit Laundry
Storage
Swimming Pool
1374 Tarflower Dr - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Winter Springs

1374 Tarflower Dr, Winter Springs, FL 32708

Affordable

3 beds

2 baths

$2,795

House for rent

109 Lisa Loop - Photo 1 of 1

4d ago

Our team has verified this company

Verified

109 Lisa Loop Winter Springs, FL 32708

109 Lisa Loop, Winter Springs, FL 32708

Affordable | Garage parking | Outdoor space

4 beds

3 baths

$2,945

$2,825

Price drop

House for rent

Available Aug 8

Top amenities
Garage Parking
805 Lewis Pl - Photo 1 of 1

1d ago

Cheap house for rent in Longwood

805 Lewis Pl, Longwood, FL 32750

Affordable | In-unit laundry | Garage parking

4 beds

2 baths

$2,850

House for rent

Top amenities
Ceiling Fan
Dishwasher
In-Unit Laundry
On-Site Laundry
184 Norris Pl - Photo 1 of 1

4d ago

Cheap house for rent in Casselberry

184 Norris Pl, Casselberry, FL 32707

Affordable | Garage parking | Storage

4 beds

3 baths

$3,799

House for rent

Available Sep 15

Top amenities
Storage
Showing 1 - 25 of 25 results
Home > House Rentals in Winter Springs > Highlands > Highlands Cheap Houses For Rent
Updated: September 20, 2025

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Discover houses for rent in Highlands, Winter Springs, FL

🌇Available cheap house rentals25 houses
💰Best rent deal181 Garden Dr
⭐Popular amenities, ,
🏠With photos