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Cheap Houses for Rent in Highlands, Winter Springs, FL

25 rentals

300 Colony Drive #3 - Photo 1 of 1

4d ago

Cheap house for rent in Casselberry

Quiet home in Casselberry

300 Colony Drive #3, Casselberry, FL 32707

Affordable | In-unit laundry | Dishwasher

1 bed

1 bath

$800

House for rent

Available Dec 13

Top amenities
In-Unit Laundry
Microwave
On-Site Laundry
181 Garden Drive - Photo 1 of 1

5d+ ago

Cheap North Orlando townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

181 Garden Drive, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

2 beds

1 bath

$1,125

House for rent

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

5d+ ago

Cheap North Orlando house for rent in Winter Springs

122 Lori Anne Ln, Winter Springs, FL 32708

Affordable

2 beds

1 bath

$1,199

House for rent

130 N Edgemon Ave - Photo 1 of 1

1d ago

Cheap North Orlando house for rent in Winter Springs

130 N Edgemon Ave 4BED 3BATH

130 N Edgemon Ave, Winter Springs, FL 32708

Affordable | In-unit laundry | Garage parking

4 beds

3 baths

$1,200

House for rent

Top amenities
Assigned Parking
Fireplace
Garage Parking
In-Unit Laundry
1142 Landmark Lane - Photo 1 of 1

5d+ ago

Cheap house for rent in Casselberry

Single Family Residence - CASSELBERRY, FL

1142 Landmark Lane, Casselberry, FL 32707

Affordable | In-unit laundry | Storage

2 beds

1 bath

$1,350

House for rent

Top amenities
In-Unit Laundry
On-Site Laundry
326 San Rafael St - Photo 1 of 1
No deposit

5d+ ago

Cheap house for rent in Winter Springs

326 San Rafael St, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

1 bed

1 bath

$1,350

House for rent

Top amenities
Dishwasher
In-Unit Laundry

Nearby rental good for eco-living

$1,125

North Orlando

Nearby rental good for pet owners

$1,895

Casselberry

40 Fairfax Avenue - Photo 1 of 1

5d+ ago

Cheap North Orlando house for rent in Winter Springs

40 N Fairfax Ave

40 Fairfax Avenue, Winter Springs, FL 32708

Affordable | In-unit laundry | Air conditioning

2 beds

1 bath

$1,450

House for rent

Top amenities
In-Unit Laundry
732 Willow Dr - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Springs

732 Willow Dr, Winter Springs, FL 32708

Affordable

2 beds

2 baths

$1,600

House for rent

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624 Huntly Lane - Photo 1 of 1

5d+ ago

Cheap Highlands townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

624 Huntly Lane, Winter Springs, FL 32708

Affordable | Garage parking

2 beds

2 baths

$1,680

House for rent

647 Redwood Dr - Photo 1 of 1

10h ago

Our team has verified this company

Verified

647 Redwood Dr, Winter Springs, FL 32708

Affordable | Garage parking | High ceilings

3 beds

2 baths

$1,950

$1,780

Price drop

House for rent

Available Nov 14

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Find sweet deals near Highlands

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

$2,000

Highlands

$1,780

Winter Springs

$2,265

Winter Springs

$1,350

Casselberry

102 Kristi Ann Court - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Winter Springs

House for rent

956 Osceola Trl - Photo 1 of 1

5d+ ago

Cheap house for rent in Casselberry

956 Osceola Trl, Casselberry, FL 32707

Affordable | On-site laundry | Storage

3 beds

2 baths

$1,895

House for rent

Available Dec 18

Top amenities
Concierge Service
On-Site Laundry
424 Club Drive - Photo 1 of 1

5d+ ago

Cheap Highlands townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

424 Club Drive, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

3 beds

2 baths

$2,000

House for rent

Top amenities
Dishwasher
In-Unit Laundry
503 Evergreen Avenue - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

503 Evergreen Ave Winter Springs, FL 32708

503 Evergreen Avenue, Winter Springs, FL 32708

Affordable | Outdoor space

4 beds

2 baths

$2,070

House for rent

Available Nov 19

20 20 North 2nd Street - Photo 1 of 1

5d+ ago

Cheap North Orlando house for rent in Winter Springs

4 Bedroom Pet-Friendly Home in WINTER SPRINGS, FL with Main Street Renewal

20 20 North 2nd Street, Winter Springs, FL 32708

Affordable | Storage | Outdoor space

4 beds

2 baths

$2,125

House for rent

312 Moss Road - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

312 S Moss Rd Winter Springs, FL 32708

312 Moss Road, Winter Springs, FL 32708

Affordable | Garage parking | Outdoor space

3 beds

2 baths

$2,140

House for rent

Available Nov 20

1662 Orrington Payne Place #1662 - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Casselberry

3 BR, 3 BA in Casselberry

1662 Orrington Payne Place #1662, Casselberry, FL 32707

Affordable | Hardwood floor | Walk-in closets

3 beds

3 baths

$2,250

House for rent

Available Dec 11

1662 Orrington Payne Place - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Casselberry

1662 Orrington Payne Place, Casselberry, FL 32707

Affordable | In-unit laundry | Garage parking

3 beds

2 baths

$2,250

House for rent

Top amenities
Fitness Center
Hardwood Floor
In-Unit Laundry
Swimming Pool
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543 Willow Way - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

543 Willow Way Winter Springs, FL 32708

543 Willow Way, Winter Springs, FL 32708

Affordable | Garage parking | Outdoor space

4 beds

2 baths

$2,265

House for rent

Available Nov 26

300 3rd St - Photo 1 of 1

5d+ ago

Cheap North Orlando house for rent in Winter Springs

Single Family Residence - WINTER SPRINGS, FL

300 3rd St, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

4 beds

2 baths

$2,300

House for rent

Top amenities
Dishwasher
In-Unit Laundry
Package Service
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

402 E Springtree Way - Photo 1 of 1

2d ago

Our team has verified this company

Verified

402 E Springtree Way, Lake Mary, FL 32746

Affordable | Garage parking | Hardwood floor

3 beds

2 baths

$2,570

House for rent

Available Feb 18

Top amenities
Ceiling Fan
Garage Parking
615 Anhinga Road #NA - Photo 1 of 1

5d+ ago

Cheap Highlands house for rent in Winter Springs

$2,700 - 3 Bedroom 2 Bathroom House In Winter Springs With Great Amenities

615 Anhinga Road #NA, Winter Springs, FL 32708

Affordable | Garage parking | Dishwasher

3 beds

2 baths

$2,700

House for rent

Available Jan 1

Top amenities
Assigned Parking
Dishwasher
1968 Downs Ct - Photo 1 of 1

2d ago

Our team has verified this company

Verified

1968 Downs Ct, Lake Mary, FL 32746

Affordable | On-site laundry | Garage parking

4 beds

2 baths

$3,205

$2,775

Price drop

House for rent

Available Nov 25

Top amenities
Ceiling Fan
High Ceilings
On-Site Laundry
Showing 1 - 25 of 25 results
Home > House Rentals in Winter Springs > Highlands > Highlands Cheap Houses For Rent
Updated: December 19, 2025

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Discover houses for rent in Highlands, Winter Springs, FL

🌇Available cheap house rentals25 houses
💰Best rent deal300 Colony Drive #3
⭐Popular amenities, ,
🏠With photos