Deals & Discount Filters
Cheap Apartments for Rent in Winter Park, FL
1,833 Rentals
-
4 BEDS, 2 BATHS$2,500 -
3 BEDS, 2.5 BATHS$2,5002421 Laura Pl
2421 Laura Pl, Orlando, FL 32803 -
3 BEDS, 2.5 BATHS$2,595
216 Harvard St
216 Harvard St, Orlando, FL 32804 -
-
4 BEDS, 2 BATHS$2,5991483 Glastonberry Rd
1483 Glastonberry Rd, Maitland, FL 32751 -
3 BEDS, 2.5 BATHS$2,6001575 Lawndale Cir
1575 Lawndale Cir, Winter Park, FL 32792 -
-
4 BEDS, 2 BATHS$2,650950 Hedgewood Ct
950 Hedgewood Ct, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$2,6501994 Canny Cv
1994 Canny Cv, Winter Park, FL 32792 -
4 BEDS, 2 BATHS$2,650
950 Hedgewood Ct
950 Hedgewood Ct, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$2,675
2460 Firstlight Wy
2460 Firstlight Wy, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$2,675
1986 Canny Cv
1986 Canny Cv, Winter Park, FL 32792 -
4 BEDS, 3 BATHS$2,6757872 Pleasant Pine Cir
7872 Pleasant Pine Cir, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,6802224 King Richards Ct
2224 King Richards Ct, Winter Park, FL 32792 -
-
3 BEDS, 2.5 BATHS$2,7002021 Canny Cv
2021 Canny Cv, Winter Park, FL 32792 -
4 BEDS, 2 BATHS$2,700724 Forest Glen Ct
724 Forest Glen Ct, Maitland, FL 32751 -
2 BEDS, 2 BATHS$2,7001725 Firehouse Ln Unit 207
1725 Firehouse Ln, Orlando, FL 32814 -
2 BEDS, 2 BATHS$2,700
Updated 2/2 with attached 1 car garage right in Baldwin Park!
1725 Firehouse Ln, Orlando, FL 32814 -
3 BEDS, 2 BATHS$2,7642007 Cornell Ave Unit ID1032296P
2007 Cornell Ave, Winter Park, FL 32789 -
-
3 BEDS, 2 BATHS$2,8001055 Cherokee Ave
1055 Cherokee Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$2,8001315 Westchester Ave
1315 Westchester Ave, Winter Park, FL 32789 -
3 BEDS, 2.5 BATHS$2,800
1957 Canny Cv
1957 Canny Cv, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$2,80041 E Spruce St
41 E Spruce St, Orlando, FL 32804 -
3 BEDS, 2 BATHS$2,8802992 Chantilly Ave
2992 Chantilly Ave, Winter Park, FL 32789 -
-
3 BEDS, 2 BATHS$2,9002128 Sycamore Dr
2128 Sycamore Dr, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,9003413 Bowman Dr
3413 Bowman Dr, Winter Park, FL 32792 -
-
3 BEDS, 2 BATHS$2,9992080 Thunderbird Trail
2080 Thunderbird Trail, Maitland, FL 32751 -
3 BEDS, 2 BATHS$3,0001891 Oglesby Ave
1891 Oglesby Ave, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$3,0004044 Tenita Dr
4044 Tenita Dr, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$3,000
1891 Oglesby Ave
1891 Oglesby Ave, Winter Park, FL 32789 -
2 BEDS, 1 BATH$3,0691307 Formosa Ave Unit ID1250011P
1307 Formosa Ave, Winter Park, FL 32789 -
-
3 BEDS, 2 BATHS$3,2503707 Pelican Ln
3707 Pelican Ln, Orlando, FL 32803 -
4 BEDS, 3 BATHS$3,250521 Brookside Cir
521 Brookside Cir, Maitland, FL 32751 -
2 BEDS, 2 BATHS$3,250
206 Quayside Cir Unit 503
206 Quayside Cir, Maitland, FL 32751 -
-
3 BEDS, 2 BATHS$3,2951807 N Park Ave
1807 N Park Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$3,400690 Osceola Ave Unit 203
690 Osceola Ave, Winter Park, FL 32789
Showing 42 of 282 results, Page 6 of 7
Winter Park at a Glance
Renting in Winter Park
Average Rental Rates and Apartment Sizes
- Apartment Type Average Sq Ft Average Rent
- Studio 537 Sq Ft $1,394 / mo
- 1 Bedroom 707 Sq Ft $1,459 / mo
- 2 Bedrooms 1,020 Sq Ft $1,729 / mo
- 3 Bedrooms 1,273 Sq Ft $2,006 / mo
- 4 Bedrooms 1,506 Sq Ft $1,544 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Four Seasons 594 Sq Ft $1,258/mo
- Winter Park Pines Merrie Oaks 594 Sq Ft $1,258/mo
- Winter Park Pines 700 Sq Ft $1,414/mo
- Winter Park Woods 764 Sq Ft $1,424/mo
- Laurel Springs 737 Sq Ft $1,432/mo
- Eastbrook 726 Sq Ft $1,454/mo
- Lake Howell 746 Sq Ft $1,541/mo
- Winter Park Estates 678 Sq Ft $1,551/mo
- Cedarwood Village 668 Sq Ft $1,575/mo
- Villas of Casselberry 733 Sq Ft $1,580/mo
Getting Around Winter Park
Education
Data provided by GreatSchools.org 2025 © 2025. All rights reserved.
tooltips
Submitting Request
Thank You
About Our Deals
Apartment Finder utilizes the industry's largest and most complete database of real-time rents and availabilities to help you find an amazing deal on your next rental.
Price Drop
Apartment communities change their rental rates often - sometimes multiple times a day. We track the changes and keep you up to date when a rental rate decreases.
Best Value
"Best value" units are located in buildings rated three stars or higher. We label apartment rentals that are priced significantly less than similar high-quality units nearby.
Rent Specials
Apartment communities regularly advertise deals for new residents. Whether it's a move-in special or a free tv, we locate the rentals that offer a little something extra when you sign your lease.
Note: Based on community-supplied data and independent market research. Subject to change without notice.