1 BED, 1 BATH
$1,250
Deals & Discount Filters
Apartments under $2,000 for Rent in Winter Park, FL
1,072 Rentals
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2 BEDS, 2.5 BATHS$1,6503374 Cedar Springs Pl
3374 Cedar Springs Pl, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,850
419 Warrenton Rd
419 Warrenton Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,5752530 Kamnic Ct
2530 Kamnic Ct, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$1,6501695 Lee Rd Unit A101
1695 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,600
1695 Lee Rd Unit C103
1695 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,445
7302 Swallow Run Unit 7302
7302 Swallow Run, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,600
3254 Howell Branch Rd
3254 Howell Branch Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,5007340 Swallow Run Unit 7340
7340 Swallow Run, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,4503651 N Goldenrod Rd Unit 110
3651 N Goldenrod Rd, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$1,900
3220 Oak Lawn Pl
3220 Oak Lawn Pl, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,500
1695 Lee Rd Unit B204
1695 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 1.5 BATHS$1,600
2523 Alexa Ct
2523 Alexa Ct, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,8002510 Boyd Ave
2510 Boyd Ave, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,6001419 Virginia Dr
1419 Virginia Dr, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,600
5301 Andrus Ave
5301 Andrus Ave, Orlando, FL 32810 -
STUDIO, 1 BATH$1,900
1470 Lake Baldwin Ln Unit C
1470 Lake Baldwin Ln, Orlando, FL 32814 -
2 BEDS, 1 BATH$1,275
2075 Howell Branch Rd Unit 101
2075 Howell Branch Rd, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,315385 Lime St
385 Lime St, Eatonville, FL 32751 -
2 BEDS, 1 BATH$1,75013 E Winter Park St
13 E Winter Park St, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,495
1416 Beatrice Dr
1416 Beatrice Dr, Orlando, FL 32810 -
1 BED, 1 BATH$1,299
524 Georgetown Dr Unit B
524 Georgetown Dr, Casselberry, FL 32707 -
2 BEDS, 1 BATH$1,600
4521 Edgewater Dr
4521 Edgewater Dr, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,5754418 Eli St
4418 Eli St, Orlando, FL 32804 -
1 BED, 1 BATH$1,4502512 Musselwhite Ave Unit 3
2512 Musselwhite Ave, Orlando, FL 32804 -
1 BED, 1 BATH$1,099
301 Clark St
301 Clark St, Eatonville, FL 32751 -
1 BED, 1 BATH$250
421 E Kennedy Blvd
421 E Kennedy Blvd, Eatonville, FL 32751 -
2 BEDS, 2.5 BATHS$1,5453004 George Mason Ave Unit K5d
3004 George Mason Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,6952450 Harbour Way
2450 Harbour Way, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$2,0002404 Gallery View Dr
2404 Gallery View Dr, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,850
419 Warrenton Rd Unit 419
419 Warrenton Rd, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,675
3282 Oak Lake Pl
3282 Oak Lake Pl, Winter Park, FL 32792 -
1 BED, 1 BATH$1,399
655 Trinidad Ct Unit 655
655 Trinidad Ct, Winter Park, FL 32792 -
3 BEDS, 1.5 BATHS$1,795731 W Comstock Ave
731 W Comstock Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,3751000 S Semoran Blvd Unit 806
1000 S Semoran Blvd, Winter Park, FL 32792 -
3 BEDS, 1 BATH$1,795
830 Carver St
830 Carver St, Winter Park, FL 32789 -
1 BED, 1 BATH$1,400
Grdyn House Unit 1
1855 Eastbrook Blvd, Winter Park, FL 32792 -
1 BED, 1 BATH$950
Grdyn House
1855 Eastbrook Blvd, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$1,9505139 Oak Hill Dr
5139 Oak Hill Dr, 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, 1.5 BATHS$1,990
825 Driver Ave
825 Driver Ave, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,500
1695 Lee Rd Unit Apartment A103
1695 Lee Rd, Winter Park, FL 32789
Showing 42 of 171 results, Page 3 of 5
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 $1,423 / mo
- 1 Bedroom 706 Sq Ft $1,479 / mo
- 2 Bedrooms 1,021 Sq Ft $1,780 / mo
- 3 Bedrooms 1,273 Sq Ft $1,992 / 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
- Winter Park Pines 711 Sq Ft $1,401/mo
- Eastbrook 743 Sq Ft $1,412/mo
- Winter Park Woods 761 Sq Ft $1,414/mo
- Cedarwood Village 681 Sq Ft $1,417/mo
- Carlton Arms 730 Sq Ft $1,423/mo
- Four Seasons 668 Sq Ft $1,460/mo
- Albert Lee Ridge 743 Sq Ft $1,478/mo
- Lake Howell 733 Sq Ft $1,503/mo
- Villas of Casselberry 738 Sq Ft $1,513/mo
- Winter Park Estates 714 Sq Ft $1,541/mo
Education
Data provided by GreatSchools.org 2025 © 2025. All rights reserved.
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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.