3 BEDS, 2 BATHS
$2,195
Deals & Discount Filters
Houses for Rent in Winter Park, FL
86 Rentals
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4 BEDS, 2 BATHS$4,0001815 Barker Dr
1815 Barker Dr, Winter Park, FL 32789 -
4 BEDS, 3.5 BATHS$3,600
1461 Lone Feather Trail
1461 Lone Feather Trail, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,200
1931 Carrigan Ave
1931 Carrigan Ave, Winter Park, FL 32792 -
4 BEDS, 5 BATHS$17,000
1742 Temple Dr
1742 Temple Dr, Winter Park, FL 32789 -
4 BEDS, 3 BATHS$2,800
2907 Little John Rd
2907 Little John Rd, Winter Park, FL 32792 -
4 BEDS, 3 BATHS$5,250
1640 Palm Ave
1640 Palm Ave, Winter Park, FL 32789 -
4 BEDS, 2.5 BATHS$6,950
1420 Lyndale Blvd
1420 Lyndale Blvd, Maitland, FL 32751 -
4 BEDS, 3 BATHS$3,490
1511 E Horatio Ave
1511 E Horatio Ave, Maitland, FL 32751 -
3 BEDS, 2 BATHS$3,950
4461 Trapp Ln
4461 Trapp Ln, Orlando, FL 32814 -
1 BED, 1 BATH$1,200
301 Clark St
301 Clark St, Eatonville, FL 32751 -
2 BEDS, 2 BATHS$2,750
814 Malone Dr
814 Malone Dr, Orlando, FL 32810 -
3 BEDS, 2 BATHS$2,400
1044 N Bumby Ave
1044 N Bumby Ave, Orlando, FL 32803 -
5 BEDS, 3 BATHS$3,040
2900 N Mills Ave
2900 N Mills Ave, Orlando, FL 32803 -
3 BEDS, 2 BATHS$1,845
514 Carver Blvd
514 Carver Blvd, Orlando, FL 32810 -
4 BEDS, 2 BATHS$3,500
2120 Deloraine Trail
2120 Deloraine Trail, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,6502 bedroom 2 bath condo in Parkview Village of Winter Park
2936 Antique Oaks Cir, Winter Park, FL 32792 -
3 BEDS, 1.5 BATHS$2,095731 W Comstock Ave
731 W Comstock Ave, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,500
2743 Sanbina St
2743 Sanbina St, Winter Park, FL 32789 -
4 BEDS, 2 BATHS$2,099
717 Denton Rd
717 Denton Rd, Winter Park, FL 32792 -
4 BEDS, 2 BATHS$3,800
1313 Buckingham Rd
1313 Buckingham Rd, Winter Park, FL 32789 -
1 BED, 1 BATH$1,200
One bedroom apt 7 or 12 months furnish or unfurnished. Apartamento disponible amueblado o sin mue...
3075 Aaron Burr Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$2,550
Beautiful 2 bedroom, 2 bath Condo located in Winter Park
110 Killarney Bay Ct, Winter Park, FL 32789 -
5 BEDS, 4 BATHS$3,800
SPACIOUS Two Story Beautiful 5/4 Home in The Enclave At Aloma!
7993 Pleasant Pine Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,740
Rent Special: Receive $100 in rent credit for the first three months with a 12-month lease!
7429 Daniel Webster Dr, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,550
COMING SOON! 5/1/26 2/2 Upgraded Condo in Winter Park**
7722 Country Pl, Winter Park, FL 32792 -
3 BEDS, 3 BATHS$3,995
1667 Mizell Ave
1667 Mizell Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,450
Newly remodeled 2/2 condo Winter Park $300. incentive for move in by 2/15/2025
3651 N Goldenrod Rd, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$3,475
Fabulous & Furnished in Winter Park!
1850 Whitehall Dr, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,725
Townhouse in Winter Park 2/2
609 Montego Bay Ct, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,395
3146 Dwarf Pine Ave
3146 Dwarf Pine Ave, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$2,650
1777 Indiana Ave
1777 Indiana Ave, Winter Park, FL 32789 -
1 BED, 1 BATH$1,050
525 S Lakemont Ave
525 S Lakemont Ave, Winter Park, FL 32792 -
4 BEDS, 2 BATHS$2,650
1813 E Cheryl Dr
1813 E Cheryl Dr, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,900
4800 Tangerine Ave
4800 Tangerine Ave, Winter Park, FL 32792 -
4 BEDS, 3 BATHS$4,695
1525 Palmer Ave
1525 Palmer Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,399
108 E Winter Park St
108 E Winter Park St, Orlando, FL 32804 -
1 BED, 1 BATH$1,800
1233 Virginia Dr
1233 Virginia Dr, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,750
College Park 2 Bed w/Bonus Room
12 E Preston St, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,290
Affordable 2/1 Duplex Available Immediately!! Near I-4!
106 People St, Eatonville, FL 32751 -
2 BEDS, 1 BATH$1,425
Cozy 2/1 Duplex - College Park
121 E Evans St, Orlando, FL 32804 -
5 BEDS, 4 BATHS$3,475
2708 Formosa Ave
2708 Formosa Ave, Orlando, FL 32804
Showing 42 of 86 results, Page 2 of 3
Winter Park at a Glance
Renting in Winter Park
Average Rental Rates and Apartment Sizes
- Apartment Type Average Sq Ft Average Rent
- Studio 535 Sq Ft $1,369 / mo
- 1 Bedroom 706 Sq Ft $1,444 / mo
- 2 Bedrooms 1,021 Sq Ft $1,753 / mo
- 3 Bedrooms 1,273 Sq Ft $2,033 / mo
- 4 Bedrooms 1,506 Sq Ft $1,775 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Laurel Springs 729 Sq Ft $1,390/mo
- Winter Park Woods 757 Sq Ft $1,394/mo
- Winter Park Pines 707 Sq Ft $1,403/mo
- Whisperwood 712 Sq Ft $1,430/mo
- Eastbrook 751 Sq Ft $1,460/mo
- Cedarwood Village 663 Sq Ft $1,515/mo
- Lake Howell 749 Sq Ft $1,549/mo
- Glenmoor 720 Sq Ft $1,552/mo
- Windward Square 784 Sq Ft $1,562/mo
- Winter Park Estates 730 Sq Ft $1,573/mo
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Data provided by GreatSchools.org 2025 © 2025. All rights reserved.
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Note: Based on community-supplied data and independent market research. Subject to change without notice.