2 BEDS, 2 BATHS
$1,600
Deals & Discount Filters
Apartments under $2,000 for Rent in Winter Park, FL
1,229 Rentals
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2 BEDS, 2 BATHS$1,5007340 Swallow Run Unit 7340
7340 Swallow Run, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,5752918 Antique Oaks Cir Unit 26
2918 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,7502304 Inagua Way Unit 2304
2304 Inagua Way, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,675
4616 N Goldenrod Rd
4616 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,295
3651 N Goldenrod Rd Unit B207
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,900
652 St Johns Ct Unit 652
652 St Johns Ct, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,6503045 Aaron Burr Ave Unit 12D
3045 Aaron Burr Ave, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,6001695 Lee Rd Unit B204
1695 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,620
1941 Lanier Ct
1941 Lanier Ct, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,750
614 St Johns Ct Unit 614
614 St Johns Ct, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,495
7302 Swallow Run Unit 7302
7302 Swallow Run, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,6507338 Swallow Run Unit 7338
7338 Swallow Run, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,5001695 Lee Rd Unit B114
1695 Lee Rd, Winter Park, FL 32789 -
1 BED, 1 BATH$1,400
1695 Lee Rd Unit C110
1695 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,800
205 Lewfield Cir Unit 205
205 Lewfield Cir, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,550
190 Ventris Ave W
190 Ventris Ave W, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,6004418 Eli St
4418 Eli St, Orlando, FL 32804 -
1 BED, 1 BATH$1,099301 Clark St
301 Clark St, Eatonville, FL 32751 -
1 BED, 1 BATH$1,049
2517 Caper Ln Unit 205
2517 Caper Ln, Maitland, FL 32751 -
1 BED, 1 BATH$1,350
524 Georgetown Dr Unit B
524 Georgetown Dr, Casselberry, FL 32707 -
2 BEDS, 1 BATH$1,450
2075 Howell Branch Rd Unit 101
2075 Howell Branch Rd, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,6504521 Edgewater Dr
4521 Edgewater Dr, Orlando, FL 32804 -
2 BEDS, 1 BATH$2,000109 E WINTER PARK St
109 E WINTER PARK St, ORLANDO, FL 32804 -
1 BED, 1 BATH$250
421 E Kennedy Blvd
421 E Kennedy Blvd, Eatonville, FL 32751 -
1 BED, 1 BATH$1,550
1140 S Orlando Ave Unit E2
1140 S Orlando Ave, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,850
250 Cedarwood Dr
250 Cedarwood Dr, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,75017 W Winter Park St
17 W Winter Park St, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,5951695 Lee Rd Unit Apartment A103
1695 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,4957302 Swallow Run Unit 7302
7302 Swallow Run, Winter Park, FL 32792 -
3 BEDS, 1.5 BATHS$1,950
731 W Comstock Ave
731 W Comstock Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,385
1000 S Semoran Blvd Unit 806
1000 S Semoran Blvd, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$1,7955523 Cretan Way
5523 Cretan Way, Winter Park, FL 32792 -
3 BEDS, 1 BATH$1,995830 Carver St
830 Carver St, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,950
4800 Tangerine Ave
4800 Tangerine Ave, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$1,950
7454 Wynnewood Square
7454 Wynnewood Square, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,000
5139 Oak Hill Dr
5139 Oak Hill Dr, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,4953011 George Mason Ave Unit 1-2E
3011 George Mason Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,6003254 Howell Branch Rd Unit Howell Branch Rd - 3254
3254 Howell Branch Rd, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,750
2304 Inagua Way
2304 Inagua Way, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,455
2500 Lee Rd Unit Apt 103
2500 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,620
1941 Lanier Ct
1941 Lanier Ct, Winter Park, FL 32792
Showing 42 of 165 results, Page 3 of 4
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 $1,409 / mo
- 1 Bedroom 706 Sq Ft $1,471 / mo
- 2 Bedrooms 1,021 Sq Ft $1,754 / mo
- 3 Bedrooms 1,273 Sq Ft $2,030 / mo
- 4 Bedrooms 1,506 Sq Ft $1,940 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Lake Howell 737 Sq Ft $1,580/mo
- Fairview 733 Sq Ft $1,862/mo
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Note: Based on community-supplied data and independent market research. Subject to change without notice.