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Cheap Apartments 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

$1,195

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

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

$1,400

House for rent

Top amenities
Dishwasher
In-Unit Laundry
124 Cory Ln - Photo 1 of 1

5d+ ago

Cheap apartment for rent in Winter Springs

Apartment - WINTER SPRINGS, FL

124 Cory Ln, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

2 beds

2 baths

$1,425

Apartment for rent

Top amenities
In-Unit Laundry
429 Sheoah Blvd #12 - Photo 1 of 1

5d+ ago

Cheap Highlands condo for rent in Winter Springs

Condo for rent

40 N Fairfax Ave - Photo 1 of 1

5d+ ago

Cheap North Orlando house for rent in Winter Springs

40 N Fairfax Ave

40 N Fairfax Ave, Winter Springs, FL 32708

Affordable | In-unit laundry | Air conditioning

2 beds

1 bath

$1,600

House for rent

Top amenities
In-Unit Laundry

Nearby rental good for eco-living

Nearby rental good for pet owners

$1,950

Winter Springs

46 N Fairfax Ave #40 - Photo 1 of 1

5d+ ago

Cheap North Orlando apartment for rent in Winter Springs

Apartment - WINTER SPRINGS, FL

46 N Fairfax Ave #40, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

2 beds

1 bath

$1,600

Apartment for rent

Top amenities
In-Unit Laundry
10 Sheoah Blvd #8 - Photo 1 of 1

5d+ ago

Cheap Highlands condo for rent in Winter Springs

Condominium - Other City - In The State Of Florida, FL

10 Sheoah Blvd #8, Winter Springs, FL 32708

Affordable

2 beds

2 baths

$1,850

$1,700

Price drop

Condo for rent

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102 Kristi Ann Ct - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Winter Springs

House for rent

420 San Gabriel St #NA - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Springs

420 San Gabriel St #NA, Winter Springs, FL 32708

Affordable | In-unit laundry | Assigned parking

2 beds

1 bath

$1,850

House for rent

Available Oct 14

Top amenities
Assigned Parking
Dishwasher
In-Unit Laundry
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Find sweet deals near Highlands

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

$1,595

Highlands

$1,895

Highlands

$1,915

Winter Springs

$1,425

Winter Springs

276 San Gabriel St - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Springs

Single Family Residence - WINTER SPRINGS, FL

276 San Gabriel St, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

3 beds

2 baths

$1,850

House for rent

Top amenities
In-Unit Laundry
On-Site Laundry
Storage
Swimming Pool
651 Macduff Ln Apt B #Apt B - Photo 1 of 1

4d ago

Cheap Highlands house for rent in Winter Springs

651 Macduff Ln Apt B #Apt B, Winter Springs, FL 32708

Affordable | Garage parking | Dishwasher

3 beds

2 baths

$1,895

House for rent

Top amenities
Dishwasher
647 Redwood Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

647 Redwood Dr, Winter Springs, FL 32708

Affordable

3 beds

2 baths

$1,915

House for rent

Available Nov 21

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 | Swimming pool

3 beds

2 baths

$1,950

House for rent

309 San Gabriel St - Photo 1 of 1

5d+ 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
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

$2,000

House for rent

Top amenities
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
227 San Gabriel St - Photo 1 of 1
3D tour

2d ago

Cheap house for rent in Winter Springs

Affordable | Dishwasher | Swimming pool

3 beds

2 baths

$2,095

House for rent

Top amenities
Microwave
Swimming Pool
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305 S Edgemon Ave - Photo 1 of 1

5d+ ago

Cheap North Orlando house for rent in Winter Springs

Affordable

3 beds

2 baths

$2,200

House for rent

20 2nd St - 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 2nd St, Winter Springs, FL 32708

Affordable | Swimming pool

4 beds

2 baths

$2,240

House for rent

640 Macduff Ln #A - Photo 1 of 1

5d+ ago

Cheap Highlands apartment for rent in Winter Springs

640 Macduff Ln #A, Winter Springs, FL 32708

Affordable | In-unit laundry | Garage parking

3 beds

2 baths

$2,300

Apartment for rent

Top amenities
High Ceilings
In-Unit Laundry
640 Macduff Ln #B - Photo 1 of 1

5d+ ago

Cheap Highlands apartment for rent in Winter Springs

640 Macduff Ln #B, Winter Springs, FL 32708

Affordable | In-unit laundry | Garage parking

3 beds

2 baths

$2,400

Apartment for rent

Top amenities
High Ceilings
In-Unit Laundry
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

1048 N Us Highway 17 92 #1 - Photo 1 of 1

5d+ ago

Cheap house for rent in Longwood

1048 N Us Highway 17 92 #1, Longwood, FL 32750

Affordable | Business center | Outdoor space

1 bed

1 bath

$2,900

House for rent

Available Nov 1

1968 Downs Ct - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1968 Downs Ct, Lake Mary, FL 32746

Affordable | On-site laundry | Garage parking

4 beds

3 baths

$3,145

$3,020

Price drop

House for rent

Available Nov 25

Top amenities
Ceiling Fan
High Ceilings
On-Site Laundry
Showing 1 - 25 of 25 results
Home > Apartments in Winter Springs > Highlands > Highlands Cheap Apartments For Rent
Updated: October 29, 2025

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Looking for cheap apartments in Highlands, Winter Springs, FL near you?

💸Lowest price$1,195
🔑Available apartment rentals25
💰Best rent deal181 Garden Dr
✨Popular amenities, ,
🧦In-unit laundry
🍽With dishwasher
🏠With photos

For more in depth rent prices, check out our Highlands, Winter Springs, FL rent data, which covers average and median rents in Highlands, Winter Springs, FL.

To know how much rent you can afford in Highlands, Winter Springs, FL, use our rent affordability calculator.

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