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Cheap Houses for Rent in Highlands, Winter Springs, FL

25 rentals

300 Colony Dr #3 - Photo 1 of 1

5d+ ago

Cheap house for rent in Casselberry

Room for rent in a quiet home in Casselberry

300 Colony Dr #3, Casselberry, FL 32707

Affordable | In-unit laundry | Dishwasher

1 bed

1 bath

$750

House for rent

Available Jan 17

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

4d 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

$1,300

House for rent

Top amenities
Dishwasher
In-Unit Laundry
1142 Landmark Ln - Photo 1 of 1

5d+ ago

Cheap house for rent in Casselberry

Single Family Residence - CASSELBERRY, FL

1142 Landmark Ln, 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
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 bath

$1,495

House for rent

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

4d ago

Cheap North Orlando house for rent in Winter Springs

46 N Fairfax Ave

46 N Fairfax Ave, Winter Springs, FL 32708

Affordable | Air conditioning | Outdoor space

2 beds

1 bath

$1,500

House for rent

44 N Fairfax Ave - Photo 1 of 1

4d ago

Cheap North Orlando house for rent in Winter Springs

44 N Fairfax Ave

44 N Fairfax Ave, Winter Springs, FL 32708

Affordable | Air conditioning

2 beds

1 bath

$1,500

House for rent

Nearby rental good for eco-living

$1,525

Longwood

Nearby rental good for pet owners

$2,200

Sanford

40 N Fairfax Ave - Photo 1 of 1

4d 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

$1,500

House for rent

Top amenities
In-Unit Laundry
685 Georgia Ave - Photo 1 of 1

5d+ ago

Cheap house for rent in Longwood

685 Georgia Ave, Longwood, FL 32750

Affordable | Ceiling fan

2 beds

1 bath

$1,525

House for rent

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624 Huntly Ln - Photo 1 of 1

5d+ ago

Cheap Highlands townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

624 Huntly Ln, Winter Springs, FL 32708

Affordable | Garage parking

2 beds

2 baths

$1,680

House for rent

219 Flamingo Dr - Photo 1 of 1

4d ago

Our team has verified this company

Verified

219 Flamingo Dr Sanford, FL 32773

219 Flamingo Dr, Sanford, FL 32773

Affordable

4 beds

1 bath

$1,799

House for rent

Available Dec 22

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Find sweet deals near Highlands

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

$1,495

Winter Springs

$1,350

Casselberry

$1,799

Sanford

$1,947

Casselberry

1442 Benwick Way - Photo 1 of 1

4d ago

Cheap house for rent in Casselberry

1442 Benwick Way, Casselberry, FL 32707

Affordable | Dishwasher | Microwave

3 beds

2 baths

$1,947

House for rent

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
336 Cello Cir - Photo 1 of 1

1d ago

Our team has verified this company

Verified

336 Cello Cir, Winter Springs, FL 32708

Affordable | Garage parking | Deck

3 beds

2 baths

$2,165

House for rent

Available Jan 23

Top amenities
Ceiling Fan
251 Domus Ln - Photo 1 of 1

15h ago

Cheap house for rent in Casselberry

Affordable | In-unit laundry | Garage parking

3 beds

2 baths

$2,200

House for rent

Available Jan 27

Top amenities
Carpet
In-Unit Laundry
On-Site Laundry
Swimming Pool
1662 Orrington Payne Pl #1662 - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Casselberry

3 BR, 3 BA in Casselberry

1662 Orrington Payne Pl #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
733 Woodhaven Dr - Photo 1 of 1

4d ago

Cheap house for rent in Winter Springs

733 Woodhaven Dr, Winter Springs, FL 32708

Affordable

3 beds

2 baths

$2,275

House for rent

402 E Springtree Way - Photo 1 of 1

13h 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

$2,520

$2,370

Price drop

House for rent

Available Feb 20

Top amenities
Ceiling Fan
Garage Parking
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1260 Seminola Blvd #NA - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

RARE RENT-TO-OWN OPPORTUNITY WITH SPECIAL OFFICE/RESIDENTIAL ZONING! (Grandfathered-In)

1260 Seminola Blvd #NA, Casselberry, FL 32707

Affordable | In-unit laundry | Assigned parking

3 beds

2 baths

$2,400

House for rent

Available Sep 12

Top amenities
Air Conditioning
Assigned Parking
Business Center
Hardwood Floor
In-Unit Laundry
320 Macgregor Rd - Photo 1 of 1

6h ago

Our team has verified this company

Verified

320 Macgregor Rd, Winter Springs, FL 32708

Affordable | Garage parking | Outdoor space

3 beds

2 baths

$2,495

House for rent

Available Mar 10

Top amenities
Ceiling Fan
High Ceilings
429 Sheoah Blvd #9 - Photo 1 of 1

4d ago

Our team has verified this company

Verified

BAYTREE VILLAGE

429 Sheoah Blvd #9, Winter Springs, FL 32708

Affordable | In-unit laundry | Hardwood floor

3 beds

2 baths

$2,499

House for rent

Available Jan 1

Top amenities
In-Unit Laundry
On-Site 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 baths

$2,850

$2,700

Price drop

House for rent

Top amenities
Garage Parking
Hardwood Floor
In-Unit Laundry
Swimming Pool
264 Tavestock Loop - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

264 Tavestock Loop Winter Springs, FL 32708

264 Tavestock Loop, Winter Springs, FL 32708

Affordable | Garage parking | Outdoor space

4 beds

3 baths

$2,799

House for rent

Available Feb 4

899 Moonluster Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

899 Moonluster Dr Casselberry, FL 32707

899 Moonluster Dr, Casselberry, FL 32707

Affordable | Garage parking | Swimming pool

4 beds

4 baths

$3,280

House for rent

Available Jan 29

216 N Griffin Dr - Photo 1 of 1

2d ago

Cheap house for rent in Casselberry

Single Family Residence - CASSELBERRY, FL

216 N Griffin Dr, Casselberry, FL 32707

Affordable | In-unit laundry | Garage parking

4 beds

2 baths

$4,500

House for rent

Top amenities
Ceiling Fan
Dishwasher
Furnished
In-Unit Laundry
Showing 1 - 25 of 25 results
Home > House Rentals in Winter Springs > Highlands > Highlands Cheap Houses For Rent
Updated: February 3, 2026

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Discover houses for rent in Highlands, Winter Springs, FL

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