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Cheap Apartments for Rent in Highlands, Winter Springs, FL

25 rentals

The Avenues at Winter Springs - Photo 1 of 1

17h ago

8.6

Very good

The Avenues at Winter Springs

1 Laurel Oaks Dr, Winter Springs, FL 32708

Affordable | Carpet

1–3 beds

1–2 baths

$1,316–$1,810

Apartment for rent

46 N Fairfax Ave #46 - Photo 1 of 1

5d+ ago

Cheap North Orlando condo for rent in Winter Springs

Condominium - WINTER SPRINGS, FL

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

Affordable | In-unit laundry | Dishwasher

2 beds

1.5 baths

$1,450

Condo for rent

Top amenities
Dishwasher
In-Unit Laundry
46 N Fairfax Ave #44 - Photo 1 of 1

5d+ ago

Cheap North Orlando condo for rent in Winter Springs

Condominium - WINTER SPRINGS, FL

46 N Fairfax Ave #44, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

2 beds

1.5 baths

$1,450

Condo for rent

Top amenities
In-Unit Laundry
46 N Fairfax Ave #40 - Photo 1 of 1

5d+ ago

Cheap North Orlando condo for rent in Winter Springs

Condominium - WINTER SPRINGS, FL

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

Affordable | In-unit laundry | Dishwasher

2 beds

1.5 baths

$1,450

Condo for rent

Top amenities
Dishwasher
In-Unit Laundry
207 S Moss Rd - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

207 S Moss Rd, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

2 beds

1.5 baths

$1,495

House for rent

Top amenities
In-Unit Laundry
155 Cory Ln - Photo 1 of 1

5d+ ago

Cheap apartment for rent in Winter Springs

Affordable | In-unit laundry | On-site management

2 beds

2 baths

$1,499

Apartment for rent

Available Mar 16

Top amenities
In-Unit Laundry
On-Site Laundry
On-Site Management

Nearby rental good for eco-living

$1,700

Casselberry

Nearby rental good for pet owners

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

$1,600

Condo for rent

407 Sheoah Blvd #13 - Photo 1 of 1

5d+ ago

Cheap Highlands condo for rent in Winter Springs

407 Sheoah Blvd #13, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

2 beds

2 baths

$1,650

Condo for rent

Top amenities
In-Unit Laundry
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114 Cory Ln - Photo 1 of 1

5d+ ago

Cheap apartment for rent in Winter Springs

114 Cory Ln, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

2 beds

2 baths

$1,700

Apartment for rent

Top amenities
In-Unit Laundry
137 Garden Dr - Photo 1 of 1

5d+ ago

Cheap North Orlando townhouse for rent in Winter Springs

Garden 137

137 Garden Dr, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

2 beds

1.5 baths

$1,800

House for rent

Available Mar 1

Top amenities
Carpet
In-Unit Laundry
Microwave
On-Site Laundry
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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

$1,995

Winter Springs

$1,316–$1,810

Winter Springs

137 Garden Dr - Photo 1 of 1

5d+ ago

Cheap North Orlando townhouse for rent in Winter Springs

137 Garden Dr, Winter Springs, FL 32708

Affordable | Microwave

2 beds

2 baths

$1,800

House for rent

133 Garden Dr - Photo 1 of 1

5d+ ago

Cheap North Orlando townhouse for rent in Winter Springs

133 Garden Dr, Winter Springs, FL 32708

Affordable | Microwave

2 beds

1.5 baths

$1,800

House for rent

227 San Gabriel St #227 - Photo 1 of 1

5d+ ago

Cheap apartment for rent in Winter Springs

3 BR, 2 BA in North Orlando

227 San Gabriel St #227, Winter Springs, FL 32708

Affordable | In-unit laundry | Hardwood floor

3 beds

2 baths

$1,995

Apartment for rent

Available Oct 23

Top amenities
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
805 Buckie Dr - Photo 1 of 1

5d+ ago

Cheap Highlands house for rent in Winter Springs

805 Buckie Dr, Winter Springs, FL 32708

Affordable

3 beds

2 baths

$2,165

House for rent

132 Sundance Ct - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Springs

Single Family Residence - WINTER SPRINGS, FL

132 Sundance Ct, Winter Springs, FL 32708

Affordable | In-unit laundry | Garage parking

3 beds

2 baths

$2,200

House for rent

Top amenities
Carpet
Ceiling Fan
Garage Parking
In-Unit Laundry
130 N Edgemon Ave - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

130 N Edgemon Ave Winter Springs, FL 32708

130 N Edgemon Ave, Winter Springs, FL 32708

Affordable | Outdoor space

4 beds

3 baths

$2,240

House for rent

Available Feb 9

451 Club Dr - Photo 1 of 1

5d+ ago

Cheap Highlands house for rent in Winter Springs

451 Club Dr, Winter Springs, FL 32708

Affordable | In-unit laundry | Dishwasher

3 beds

2 baths

$2,399

$2,250

Price drop

House for rent

Top amenities
In-Unit Laundry
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1662 Orrington Payne Pl - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Casselberry

1662 Orrington Payne Pl, Casselberry, FL 32707

Affordable | In-unit laundry | Garage parking

3 beds

2.5 baths

$2,250

House for rent

Top amenities
Fitness Center
Hardwood Floor
In-Unit Laundry
Swimming Pool
1485 Oberlin Ter - Photo 1 of 1

5d+ ago

Cheap house for rent in Lake Mary

Single Family Residence - LAKE MARY, FL

1485 Oberlin Ter, Lake Mary, FL 32746

Affordable | In-unit laundry | Garage parking

3 beds

2 baths

$2,350

House for rent

Top amenities
Dishwasher
In-Unit Laundry
320 Macgregor Rd - Photo 1 of 1

1d ago

Our team has verified this company

Verified

320 Macgregor Rd, Winter Springs, FL 32708

Affordable | Garage parking | Walk-in closets

3 beds

2 baths

$2,545

$2,420

Price drop

House for rent

Available Feb 28

Top amenities
Ceiling Fan
High Ceilings
709 Heather Ln - Photo 1 of 1

1d ago

Our team has verified this company

Verified

709 Heather Ln, Winter Springs, FL 32708

Affordable | On-site laundry | Storage

3 beds

2 baths

$2,435

House for rent

Available May 15

Top amenities
On-Site Laundry
On-Site Management
Storage
119 N Alderwood St - Photo 1 of 1

5d+ ago

Cheap North Orlando house for rent in Winter Springs

119 N Alderwood St, Winter Springs, FL 32708

Affordable | In-unit laundry | Garage parking

4 beds

2 baths

$2,450

House for rent

Top amenities
In-Unit Laundry
419 Harbor Winds Ct - Photo 1 of 1

5d+ ago

Cheap Highlands townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

419 Harbor Winds Ct, Winter Springs, FL 32708

Affordable | In-unit laundry | Garage parking

3 beds

2.5 baths

$2,550

House for rent

Top amenities
Air Conditioning
Garage Parking
In-Unit Laundry
Swimming Pool
537 Sunbranch Ln - Photo 1 of 1

5d+ ago

Cheap house for rent in Casselberry

537 Sunbranch Ln, Casselberry, FL 32707

Affordable | Dishwasher | Oven

3 beds

2.5 baths

$2,600

House for rent

Showing 1 - 25 of 25 results
Home > Apartments in Winter Springs > Highlands > Highlands Cheap Apartments For Rent
Updated: March 18, 2026

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

💸Lowest price$1,316
🔑Available apartment rentals25
💰Best rent deal1 Laurel Oaks 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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