4 BEDS, 2.25 BATHS
$4,500
Deals & Discount Filters
Apartments for Rent in Winter Park, FL
1,983 Rentals
-
-
2 BEDS, 1 BATH$1,100
1701 Winter Green Blvd
1701 Winter Green Blvd, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,250
2458 Grand Teton Cir Unit 1
2458 Grand Teton Cir, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,900
1835 Biscayne Dr
1835 Biscayne Dr, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,600
1280 Gladiolas Dr
1280 Gladiolas Dr, Winter Park, FL 32792 -
2 BEDS, 1 BATH$2,150
1919 Azalea Ave
1919 Azalea Ave, Winter Park, FL 32792 -
4 BEDS, 2 BATHS$3,500
1690 Dale Ave
1690 Dale Ave, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,250
200 St Andrews Blvd Unit 1203
200 St Andrews Blvd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,795
1500 Gay Rd Unit 18C
1500 Gay Rd, Winter Park, FL 32789 -
1 BED, 1 BATH$1,050
525 S Lakemont Ave
525 S Lakemont Ave, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$3,250
1096 Azalea Ln
1096 Azalea Ln, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,785
5334 Lake Howell Rd
5334 Lake Howell Rd, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,875
644 N Knowles Ave
644 N Knowles Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,595
115 Scottsdale Square
115 Scottsdale Square, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$1,525
3007 George Mason Ave Unit H
3007 George Mason Ave, Winter Park, FL 32792 -
4 BEDS, 2.5 BATHS$4,900
2952 De Brocy Way
2952 De Brocy Way, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$2,380
645 Huntington Ave
645 Huntington Ave, Winter Park, FL 32789 -
1 BED, 1 BATH$1,295
2326 Wellington Blvd
2326 Wellington Blvd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,600
3267 Forest Oaks Ct Unit Apt 111
3267 Forest Oaks Ct, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$1,995
7473 Belle River Ct
7473 Belle River Ct, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$1,881
3392 Bougainvillea Dr
3392 Bougainvillea Dr, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$3,500
Luxury furnished 3-Bed in Winter Park
2774 Bright Bird Ln, Winter Park, FL 32792 -
8 BEDS, 6 BATHS$17,550
1860 Vía Contessa
1860 Vía Contessa, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,499
1500 Michigan Ave
1500 Michigan Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,400
3651 N Goldenrod Rd Unit B109
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,600
Upgraded 2 Bed 2 Bath Condo for Rent in Wi... Unit C206
3651 N Goldenrod Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,400
Beautiful 1/1 Wood Floors Condo for Rent i... Unit 6
2905 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,700
Excellent location Unit 4968
4968 Tangerine Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,840
Fully Furnished 2/2 Condo!
7429 Daniel Webster Dr, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,995
Charming 3-Bedroom Winter Park Home – $500...
2817 Eastern Pkwy, Winter Park, FL 32789 -
1 BED, 1 BATH$1,399
Beautiful Remodeled 1/1 Winter Park Condo ... Unit 50
2929 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,750
Charming 2-Bedroom Condo in Scenic Winter ... Unit 204
1250 S Denning Dr, Winter Park, FL 32789 -
3 BEDS, 2.5 BATHS$2,600
Grayson Square
1878 Erudite Wy, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$1,850
Cute 3/2 Townhome in Winter Park - close t...
758 Warrenton Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$2,725
FIRST MONTH FREE - Beautiful remodeled 2 ...
939 Aragon Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,675
Winter Park 2/2 Condo in Charming Parkview... Unit 79
2941 Antique Oaks Cir, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,395
Single family home in Winter Park! Availab...
1148 Park Green Pl, Winter Park, FL 32789 -
2 BEDS, 1.5 BATHS$1,725
2Bed/1.5Bath TOWNHOUSE IN WINTER PARK!! ...
4954 Tangerine Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,699
Beautiful Remodeled First Floor 2/2 Condo ... Unit 17
2917 Antique Oaks Cir, Winter Park, FL 32792 -
1 BED, 1 BATH$1,375
Beutiful 1/1 Condo x Rent in Winter Park ... Unit 612
200 St Andrews Blvd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,650
FOR RENT! Gorgeous First Floor Remodeled 2... Unit 163
3038 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$1,895
Townhome in Winter Park
200 Sandlewood Trail, Winter Park, FL 32789
Showing 42 of 322 results, Page 6 of 8
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 $1,400 / mo
- 1 Bedroom 709 Sq Ft $1,467 / mo
- 2 Bedrooms 1,020 Sq Ft $1,701 / mo
- 3 Bedrooms 1,273 Sq Ft $2,030 / mo
- 4 Bedrooms 1,506 Sq Ft $1,535 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Whisperwood 741 Sq Ft $1,395/mo
- Four Seasons 622 Sq Ft $1,412/mo
- Winter Park Pines Merrie Oaks 622 Sq Ft $1,412/mo
- Winter Park Pines 739 Sq Ft $1,414/mo
- Winter Park Woods 761 Sq Ft $1,416/mo
- Eastbrook 737 Sq Ft $1,464/mo
- Laurel Springs 746 Sq Ft $1,482/mo
- Albert Lee Ridge 743 Sq Ft $1,493/mo
- Cedarwood Village 652 Sq Ft $1,526/mo
- Glenmoor 708 Sq Ft $1,552/mo
Average Rent in Nearby Cities
(For 1 bedroom apartments)- Cities Average Rent
- Winter Park $1,598/mo
- Maitland $1,768/mo
- Fern Park $1,295/mo
- Eatonville $992/mo
- Casselberry $1,611/mo
- Longwood $1,762/mo
- Altamonte Springs $1,614/mo
- Lockhart $1,333/mo
- Orlando $1,663/mo
- Belle Isle $1,275/mo
- Pine Castle $1,183/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.