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Cheap Houses for Rent in Winter Park, FL

30 rentals available

7328 Swallow Run - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Park

7328 Swallow Run, Winter Park, FL 32792

Affordable

2 beds

2 baths

$1,500

$1,400

Price drop

House for rent

3012 Patel Dr - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Park

3012 Patel Dr, Winter Park, FL 32792

Affordable | Dishwasher

2 beds

2 baths

$1,600

House for rent

7350 Swallow Run #1 - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Winter Park

7350 Swallow Run, Winter Park, FL 32792 - 1

7350 Swallow Run #1, Winter Park, FL 32792

Affordable | Swimming pool

2 beds

2 baths

$1,650

House for rent

Available Jul 1

620 Trinidad Ct #620 - Photo 1 of 1
3D tour

5d+ ago

Cheap house for rent in Winter Park

620 Trinidad Ct #620, Winter Park, FL 32792

Affordable | Dishwasher | Carpet

2 beds

2 baths

$1,695

House for rent

Top amenities
Microwave
5523 Cretan Way - Photo 1 of 1

5h ago

Cheap townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

5523 Cretan Way, Winter Park, FL 32792

Affordable | In-unit laundry | Assigned parking

3 beds

2 baths

$1,995

$1,795

Price drop

House for rent

Top amenities
Ceiling Fan
Concierge Service
Dishwasher
In-Unit Laundry
Package Service
Storage
7454 Wynnewood Sq #188 - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Winter Park

7454 wynnewood circle - 188

7454 Wynnewood Sq #188, Winter Park, FL 32792

Affordable

3 beds

2.5 baths

$1,950

House for rent

Available Apr 1

Nearby rental good for eco-living

Nearby rental good for pet owners

$2,195

447 N Phelps Ave

3036 Patel Dr - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Park

3036 Patel Dr, Winter Park, FL 32792

Affordable

3 beds

2 baths

$2,100

House for rent

447 N Phelps Ave - Photo 1 of 1

1d ago

Cheap house for rent in Winter Park

447 N Phelps Ave, Winter Park, FL 32789

Affordable | In-unit laundry | Dishwasher

3 beds

1 bath

$2,195

House for rent

Top amenities
In-Unit Laundry
Microwave
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851 Carver St - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Park

851 Carver St, Winter Park, FL 32789

Affordable | In-unit laundry | Microwave

3 beds

2 baths

$2,250

House for rent

Top amenities
In-Unit Laundry
7800 Fernbrook Way - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Winter Park

7800 Fernbrook Way, Winter Park, FL 32792

Affordable | In-unit laundry | On-site management

3 beds

2 baths

$2,295

House for rent

Available Jun 1

Top amenities
In-Unit Laundry
On-Site Management
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Find sweet deals in Winter Park

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

$1,400

7328 Swallow Run

$1,600

3012 Patel Dr

$2,100

3036 Patel Dr

$2,195

447 N Phelps Ave

3449 Allston Ln - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Park

3449 Allston Ln, Winter Park, FL 32792

Affordable | In-unit laundry | Dishwasher

3 beds

2.5 baths

$2,350

House for rent

Top amenities
In-Unit Laundry
2619 Ambergate Rd - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Park

2619 Ambergate Rd, Winter Park, FL 32792

Affordable | Garage parking | Outdoor space

3 beds

1.5 baths

$2,350

House for rent

2242 King Johns Ct - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Park

3 BR / 2 BA Home In Winter Park

2242 King Johns Ct, Winter Park, FL 32792

Affordable | In-unit laundry | Outdoor space

3 beds

2 baths

$2,395

House for rent

Top amenities
In-Unit Laundry
1340 Paradise Ln #1 - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Park

1340 Paradise Lane - 1

1340 Paradise Ln #1, Winter Park, FL 32792

Affordable

3 beds

2 baths

$2,400

House for rent

Available Jun 1

2379 Flamingo Way - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

2379 Flamingo Way, Winter Park, FL 32792

Affordable | In-unit laundry | Dishwasher

3 beds

2 baths

$2,400

House for rent

Top amenities
Ceiling Fan
In-Unit Laundry
Swimming Pool
3439 Allston Ln - Photo 1 of 1

3d ago

Our team has verified this company

Verified

3439 Allston Ln, Winter Park, FL 32792

Affordable | Garage parking | Outdoor space

3 beds

2.5 baths

$2,445

House for rent

Available Aug 7

Top amenities
High Ceilings
2313 Dunbury Ct - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

2313 Dunbury Ct Winter Park, FL 32792

2313 Dunbury Ct, Winter Park, FL 32792

Affordable | Garage parking | Outdoor space

3 beds

2 baths

$2,445

House for rent

Available May 21

2730 Prince John Rd - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

2730 Prince John Rd, Winter Park, FL 32792

Affordable | In-unit laundry | Garage parking

4 beds

2 baths

$2,495

House for rent

Top amenities
Ceiling Fan
Concierge Service
Garage Parking
In-Unit Laundry
On-Site Management
Package Service
Advertisement
1947 Summerfield Rd - Photo 1 of 1

1d ago

Cheap house for rent in Winter Park

1947 Summerfield Rd, Winter Park, FL 32792

Affordable | On-site management

3 beds

2 baths

$2,599

$2,499

Price drop

House for rent

Available Apr 17

Top amenities
On-Site Management
1840 Bachman Way - Photo 1 of 1

1d ago

Cheap house for rent in Winter Park

$2,500 - 3 Bedroom 2.5 Bathroom House In Winter Park

1840 Bachman Way, Winter Park, FL 32792

Affordable | In-unit laundry | Garage parking

3 beds

3 baths

$2,500

House for rent

Available Jul 10

Top amenities
Central Heat
Dishwasher
Garage Parking
Hardwood Floor
High Ceilings
In-Unit Laundry
1840 Bachman Way #NA - Photo 1 of 1

1d ago

Cheap house for rent in Winter Park

$2,500 - 3 Bedroom 2.5 Bathroom House In Winter Park With Great Amenities

1840 Bachman Way #NA, Winter Park, FL 32792

Affordable | In-unit laundry | Garage parking

3 beds

2.5 baths

$2,500

House for rent

Available Jul 10

Top amenities
Assigned Parking
Carpet
Dishwasher
Garage Parking
In-Unit Laundry
Swimming Pool
1540 Oneco Ave - Photo 1 of 1

2d ago

Cheap house for rent in Winter Park

1540 Oneco Ave, Winter Park, FL 32789

Affordable | In-unit laundry | Dishwasher

3 beds

2 baths

$2,500

House for rent

Top amenities
In-Unit Laundry
Microwave
747 Maryland Ave - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Park

747 Maryland Ave, Winter Park, FL 32789

Affordable | Outdoor space

3 beds

2 baths

$2,500

House for rent

1839 Blaine Ter - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1839 Blaine Ter, Winter Park, FL 32792

Affordable | Garage parking | Outdoor space

3 beds

2.5 baths

$2,510

House for rent

Available Jul 31

3313 Hamlet Loop - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

3313 Hamlet Loop, Winter Park, FL 32792

Affordable | Garage parking | Outdoor space

3 beds

2.5 baths

$2,550

House for rent

Available Jul 3

Top amenities
Ceiling Fan
High Ceilings
5563 Pats Pt - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

5563 Pats Pt, Winter Park, FL 32792

Affordable | On-site laundry | Garage parking

3 beds

2 baths

$2,575

House for rent

Available Jul 20

Top amenities
Ceiling Fan
Garage Parking
On-Site Laundry
Advertisement
504 Saint Dunstan Way - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

504 Saint Dunstan Way, Winter Park, FL 32792

Affordable | On-site laundry | On-site management

3 beds

2 baths

$2,935

$2,585

Price drop

House for rent

Available Jun 22

Top amenities
On-Site Laundry
On-Site Management
2530 Passamonte Dr #10E - Photo 1 of 1

5d+ ago

Cheap townhouse for rent in Winter Park

Condominium - WINTER PARK, FL

2530 Passamonte Dr #10E, Winter Park, FL 32792

Affordable | In-unit laundry | Garage parking

3 beds

2.5 baths

$2,600

House for rent

Top amenities
Garage Parking
High Ceilings
In-Unit Laundry
4190 Bear Gully Rd #1 - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Park

Bear Gully 4190 - 1

4190 Bear Gully Rd #1, Winter Park, FL 32792

Affordable | Garage parking | Dishwasher

4 beds

3 baths

$2,800

House for rent

Available May 29

Top amenities
Air Conditioning
Dishwasher
Microwave
1843 Shadyhill Ter - Photo 1 of 1

5d+ ago

Cheap house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1843 Shadyhill Ter, Winter Park, FL 32792

Affordable | In-unit laundry | Garage parking

4 beds

2.5 baths

$3,300

House for rent

Top amenities
Carpet
Garage Parking
In-Unit Laundry
On-Site Laundry
Storage
Swimming Pool
Showing 1 - 30 of 30 results
Home > House Rentals in Winter Park > Winter Park Cheap Houses For Rent
Updated: June 17, 2026

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Pet friendly houses in Winter Park, FL17 rentals

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Discover houses for rent in Winter Park, FL

🌇Available cheap house rentals30 houses
💰Best rent deal7328 Swallow Run
⭐Popular amenities, ,
🔌Utilities included
🏠With photos