3 BEDS, 2 BATHS
$2,200
Deals & Discount Filters
Apartments for Rent in Winter Park, FL
1,846 Rentals
-
-
4 BEDS, 3 BATHS$7,0001400 S Pennsylvania Ave
1400 S Pennsylvania Ave, Winter Park, FL 32789 -
3 BEDS, 2.5 BATHS$2,3003381 Hamlet Loop
3381 Hamlet Loop, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,700
3057 Aaron Burr Ave Unit 1
3057 Aaron Burr Ave, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,900
3383 Hamlet Loop
3383 Hamlet Loop, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$2,900
1447 Broad Wing Ln
1447 Broad Wing Ln, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,500
1695 Lee Rd Unit B114
1695 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 1.5 BATHS$1,895
200 St Andrews Blvd Unit 2903
200 St Andrews Blvd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$3,400
690 Osceola Ave Unit 203
690 Osceola Ave, Winter Park, FL 32789 -
2 BEDS, 1.5 BATHS$1,700
2523 Alexa Ct
2523 Alexa Ct, Winter Park, FL 32792 -
2 BEDS, 1 BATH$2,150
151 N Orlando Ave Unit 226
151 N Orlando Ave, Winter Park, FL 32789 -
3 BEDS, 2.5 BATHS$2,675
1986 Canny Cv
1986 Canny Cv, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$2,200
1417 Belgrade Ave
1417 Belgrade Ave, Orlando, FL 32803 -
3 BEDS, 2.5 BATHS$3,800
1400 Lake Baldwin Ln
1400 Lake Baldwin Ln, Orlando, FL 32814 -
3 BEDS, 2 BATHS$2,850
2514 Illinois St
2514 Illinois St, Orlando, FL 32803 -
4 BEDS, 3 BATHS$3,898
1511 E Horatio Ave
1511 E Horatio Ave, Maitland, FL 32751 -
3 BEDS, 2 BATHS$2,250
724 W Fairbanks Ave
724 W Fairbanks Ave, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,600
4418 Eli St
4418 Eli St, Orlando, FL 32804 -
3 BEDS, 2 BATHS$1,800
404 Banyon Tree Cir Unit 200
404 Banyon Tree Cir, Maitland, FL 32751 -
3 BEDS, 2.5 BATHS$2,695
216 Harvard St
216 Harvard St, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,400
496 Banyon Tree Cir Unit 104
496 Banyon Tree Cir, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,400
550 Flemming Way Unit 200
550 Flemming Way, Maitland, FL 32751 -
3 BEDS, 2 BATHS$2,245
410 Poplar Ct
410 Poplar Ct, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,290
64 Taylor Ave
64 Taylor Ave, Eatonville, FL 32751 -
3 BEDS, 3.5 BATHS$3,700
1438 Chatfield Pl
1438 Chatfield Pl, Orlando, FL 32814 -
2 BEDS, 2 BATHS$2,500
1025 Hunter Ave
1025 Hunter Ave, Orlando, FL 32804 -
3 BEDS, 2 BATHS$3,250
3707 Pelican Ln
3707 Pelican Ln, Orlando, FL 32803 -
3 BEDS, 2 BATHS$2,750
2467 Sunderland Rd
2467 Sunderland Rd, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,575
4425 Fairview Ave
4425 Fairview Ave, Orlando, FL 32804 -
3 BEDS, 1.5 BATHS$1,995
776 Carew Ave
776 Carew Ave, Orlando, FL 32804 -
1 BED, 1 BATH$1,100
2521 Caper Ln Unit 203
2521 Caper Ln, Maitland, FL 32751 -
1 BED, 1 BATH$1,200
2517 Caper Ln Unit 205
2517 Caper Ln, Maitland, FL 32751 -
3 BEDS, 2.5 BATHS$5,500
2823 Wilford Ave
2823 Wilford Ave, Orlando, FL 32814 -
2 BEDS, 1 BATH$1,565
1418 Beatrice Dr
1418 Beatrice Dr, Orlando, FL 32810 -
3 BEDS, 2 BATHS$2,350
226 Harvard St
226 Harvard St, Orlando, FL 32804 -
1 BED, 1 BATH$2,300
40 E Princeton St
40 E Princeton St, Orlando, FL 32804 -
3 BEDS, 1 BATH$2,270
3511 Backspin Ln
3511 Backspin Ln, Orlando, FL 32804 -
2 BEDS, 1.5 BATHS$1,895200 St Andrews Blvd Unit 2903
200 St Andrews Blvd, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,3991502 Michigan Ave
1502 Michigan Ave, Winter Park, FL 32789 -
2 BEDS, 2.5 BATHS$1,500
7431 Glen Oaks Way Unit 89
7431 Glen Oaks Way, Winter Park, FL 32792 -
1 BED, 1 BATH$1,300
Stylish Remodeled 1BR Condo with Pool & Low HOA – Ideal Winter Park Investment Unit N-10C
3060 George Mason Ave, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,099
2111 Biscayne Dr
2111 Biscayne Dr, Winter Park, FL 32789
Showing 42 of 284 results, Page 5 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 539 Sq Ft $1,381 / mo
- 1 Bedroom 707 Sq Ft $1,437 / mo
- 2 Bedrooms 1,019 Sq Ft $1,752 / mo
- 3 Bedrooms 1,273 Sq Ft $1,998 / mo
- 4 Bedrooms 1,506 Sq Ft $1,540 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Four Seasons 590 Sq Ft $1,348/mo
- Winter Park Pines Merrie Oaks 590 Sq Ft $1,348/mo
- Winter Park Woods 763 Sq Ft $1,379/mo
- Winter Park Pines 669 Sq Ft $1,428/mo
- Eastbrook 747 Sq Ft $1,432/mo
- Laurel Springs 741 Sq Ft $1,434/mo
- Lake Howell 747 Sq Ft $1,520/mo
- Villas of Casselberry 764 Sq Ft $1,537/mo
- Windward Square 784 Sq Ft $1,552/mo
- Glenmoor 706 Sq Ft $1,552/mo
Average Rent in Nearby Cities
(For 1 bedroom apartments)- Cities Average Rent
- Winter Park $1,591/mo
- Maitland $1,747/mo
- Fern Park $1,298/mo
- Eatonville $875/mo
- Casselberry $1,741/mo
- Longwood $1,695/mo
- Altamonte Springs $1,599/mo
- Orlando $1,650/mo
- Pine Castle $1,294/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.