2 BEDS, 1 BATH
$1,500
Deals & Discount Filters
Apartments under $2,000 for Rent in Winter Park, FL
1,302 Rentals
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2 BEDS, 1 BATH$1,9751803 Pineview Cir
1803 Pineview Cir, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,5951695 Lee Rd Unit C206
1695 Lee Rd, Winter Park, FL 32789 -
1 BED, 1 BATH$1,450
1555 Michigan Ave
1555 Michigan Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,650
1000 S Semoran Blvd Unit 815
1000 S Semoran Blvd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,400
3032 Antique Oaks Cir Unit 145
3032 Antique Oaks Cir, Winter Park, FL 32792 -
1 BED, 1 BATH$1,4001695 Lee Rd Unit C110
1695 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,6502936 Antique Oaks Cir Unit 70
2936 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,450
3651 N Goldenrod Rd Unit 110
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,775
3254 Howell Branch Rd
3254 Howell Branch Rd, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$1,725
3283 Oak Lake Pl
3283 Oak Lake Pl, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,800612 Trinidad Ct Unit 612
612 Trinidad Ct, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,6002523 Alexa Ct
2523 Alexa Ct, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,800
205 Lewfield Cir Unit 205
205 Lewfield Cir, Winter Park, FL 32792 -
1 BED, 1 BATH$1,350
4818 Tangerine Ave Unit 4818
4818 Tangerine Ave, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,500
1565 Michigan Ave
1565 Michigan Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,3603651 N Goldenrod Rd Unit C204
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,4001695 Lee Rd Unit D213
1695 Lee Rd, Winter Park, FL 32789 -
1 BED, 1 BATH$1,200
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, 1 BATH$1,695
190 Ventris Ave W
190 Ventris Ave W, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,9002884 Plaza Terrace Dr Unit 2884
2884 Plaza Terrace Dr, Orlando, FL 32803 -
1 BED, 1 BATH$1,1002517 Caper Ln Unit 205
2517 Caper Ln, Maitland, FL 32751 -
1 BED, 1 BATH$1,450
2512 Musselwhite Ave Unit 3
2512 Musselwhite Ave, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,600
4418 Eli St
4418 Eli St, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,995
2512 Musselwhite Ave Unit #1
2512 Musselwhite Ave, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,75017 W Winter Park St
17 W Winter Park St, Orlando, FL 32804 -
1 BED, 1 BATH$1,200301 Clark St
301 Clark St, Eatonville, FL 32751 -
2 BEDS, 1 BATH$1,700
2515 Formosa Ave
2515 Formosa Ave, Orlando, FL 32804 -
2 BEDS, 2.5 BATHS$1,900Gorgeous, Completely Remodeled 2/2.5 Condo in Sandlewood Creek- Winter Park!
303 Sandlewood Trail, Winter Park, FL 32789 -
1 BED, 1 BATH$1,200One 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$1,740Rent 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$1,700Excellent location Unit 4968
4968 Tangerine Ave, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,595
SPACIOUS 2BR CONDO | MOVE-IN READY | LIMITED AVAILABILITY
1695 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,600
1/2 Duplex in Winter Park
3012 Patel Dr, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,450
Newly remodeled 2/2 condo Winter Park $300. incentive for move in by 6/15/2026 Unit A104
3651 Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,4951000 S Semoran Blvd Unit 806
1000 S Semoran Blvd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,250138 Lewfield Cir
138 Lewfield Cir, Winter Park, FL 32792 -
1 BED, 1 BATH$1,050
525 S Lakemont Ave
525 S Lakemont Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,775
3254 Howell Branch Rd Unit Howell Branch Rd - 3254
3254 Howell Branch Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,950
4800 Tangerine Ave
4800 Tangerine Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,6953011 George Mason Ave Unit 1-2E
3011 George Mason Ave, Winter Park, FL 32792
Showing 42 of 148 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 $1,399 / mo
- 1 Bedroom 706 Sq Ft $1,460 / mo
- 2 Bedrooms 1,012 Sq Ft $1,759 / mo
- 3 Bedrooms 1,273 Sq Ft $2,035 / 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 742 Sq Ft $1,512/mo
- Fairview 753 Sq Ft $1,873/mo
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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.
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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.