How many houses are available in Winter Park right now?

Rentler currently shows 40 houses for rent in Winter Park. Inventory updates daily — set a listing alert if you want to catch new units as they post.

What should I look for when renting houses in Winter Park?

Compare monthly rent against parking, laundry, storage, and commute. Confirm what is included in rent, who handles maintenance, and any HOA or community rules before you apply. In Winter Park, well-priced houses can move quickly once listed.

Can I find pet-friendly houses in Winter Park?

Yes — many houses accept pets, though policies vary. Use Rentler's pet-friendly filter, then confirm breed, weight, and deposit requirements with the landlord before submitting an application.

Houses for Rent in Winter Park, FL

32 Results

$3,995

3 beds3.5 baths1,810 sqftHouse

741 Minnesota Ave, Winter Park, FL, 32789

$3,995

3 beds3.5 baths1,810 sqftHouse

737 Minnesota Ave, Winter Park, FL, 32789

$3,995

3 beds3.5 baths1,810 sqftHouse

735 Minnesota Ave, Winter Park, FL, 32789

$2,400

3 beds2.5 baths2,200 sqftHouse

258 Balfour Street, Winter Park, FL, 32789

$2,595

3 beds2 baths1,313 sqftHouse

2502 Fifeshire Drive, Winter Park, FL, 32792

$2,100

1 bed2 baths1,153 sqftHouse

250 Carolina Ave Unit 250, Winter, FL, 32789

$2,350

2 beds1 bath865 sqftHouse

521 W. Winter Park St., Orlando, FL, 32804

$2,095

2 beds2.5 baths1,550 sqftHouse

2577 Galliano Cir, Winter Park, FL, 32792

$2,995

3 beds2 bathsHouse

2545 Madeline Avenue, Winter Park, FL, 32789

$1,999

3 beds2 baths1,096 sqftHouse

1603 Winter Green Blvd, Winter Park, FL, 327922246

$2,095

3 beds1.5 baths1,514 sqftHouse

2028 Albert Lee Pkwy, Winter Park, FL, 32789

$1,195

1 bed1 bath620 sqftHouse

1600 Indiana Ave., Winter Park, FL, 32789

$1,995

2 beds1.5 baths988 sqftHouse

937 Aragon Ave, Winter Park, FL, 32789

$1,099

1 bed1 bath645 sqftHouse

2500 Lee Rd 145, Winter Park, FL, 32789

$1,795

3 beds1.5 baths1,024 sqftHouse

731 W. Comstock Avenue, Winter Park, FL, 32789

$2,940

3 beds2 baths1,295 sqftHouse

408 London Rd, Winter Park, FL, 32792

$4,500

3 beds2 baths1,668 sqftHouse

2120 Meeting Pl 101, Orlando, FL, 32814

$1,800

1 bed1 bathHouse

759 Antonette Ave, Winter Park, FL, 32789

$2,000

2 beds2 baths1,095 sqftHouse

401 Balfour Drive, Winter Park, FL, 32792

$3,300

3 beds2 baths1,771 sqftHouse

3306 Eagle Blvd, Orlando, FL, 32804

$6,250

3 beds2.5 baths2,395 sqftHouse

3602 Upper Union Rd, Orlando, FL, 32814

$3,400

3 beds2 bathsHouse

1939 Gunn Rd, Winter Park, FL, 32792

$2,750

3 beds2 baths1,450 sqftHouse

2401 Albert Lee Pkwy, Winter Park, FL, 32789

$7,995

4 beds5.5 baths3,350 sqftHouse

2234 Howard Dr, Winter Park, FL, 32789

Showing 24 of 32 results

What to Know Before Renting a House in Winter Park, FL

Single-family houses for rent in Winter Park appeal to families and renters who want yards and garage parking. Houses lease less frequently than apartments, so set alerts and act quickly when a match appears. Confirm lawn care, utility splits, pet fences, and maintenance response expectations with the landlord before signing.