1 BED, 1 BATH
$1,300
Deals & Discount Filters
Apartments under $2,000 for Rent in Winter Park, FL
1,156 Rentals
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2 BEDS, 1 BATH$1,595851 Miles Ave Unit 21
851 Miles Ave, Winter Park, FL 32789 -
2 BEDS, 1.5 BATHS$1,550
316 Scottsdale Square Unit 316
316 Scottsdale Square, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,800
616 Montego Bay Ct Unit S
616 Montego Bay Ct, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$1,9755169 Lazy Oaks Dr
5169 Lazy Oaks Dr, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,4501000 S Semoran Blvd Unit 115
1000 S Semoran Blvd, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,500
1695 Lee Rd Unit B114
1695 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,700
3057 Aaron Burr Ave Unit 1
3057 Aaron Burr Ave, Winter Park, FL 32792 -
STUDIO, 1 BATH$1,100
7417 Daniel Webster Dr Unit 3
7417 Daniel Webster Dr, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,895200 St Andrews Blvd Unit 2903
200 St Andrews Blvd, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,5751565 Michigan Ave
1565 Michigan Ave, Winter Park, FL 32789 -
1 BED, 1 BATH$1,350
200 St Andrews Blvd Unit 606
200 St Andrews Blvd, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,299
1436 Minnesota Ave
1436 Minnesota Ave, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,950
263 Blossom Ln
263 Blossom Ln, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,3503651 N Goldenrod Rd Unit B#104
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$1,8957337 Cedar Creek Ct
7337 Cedar Creek Ct, Winter Park, FL 32792 -
1 BED, 1 BATH$1,475
2500 Lee Rd Unit 244
2500 Lee Rd, Winter Park, FL 32789 -
3 BEDS, 2.5 BATHS$1,995
7473 Belle River Ct
7473 Belle River Ct, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,295
2183 Crandon Ave
2183 Crandon Ave, Winter Park, FL 32789 -
1 BED, 1 BATH$1,3504860 Tangerine Ave Unit 4860
4860 Tangerine Ave, Winter Park, FL 32792 -
4 BEDS, 2 BATHS$1,975275 N Capen Ave
275 N Capen Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,495
3651 N Goldenrod Rd Unit C204
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,795
918 Gloriosa Ave
918 Gloriosa Ave, Winter Park, FL 32789 -
2 BEDS, 2.5 BATHS$1,750
7412 Woodburn Ct
7412 Woodburn Ct, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,5754425 Fairview Ave
4425 Fairview Ave, Orlando, FL 32804 -
1 BED, 1 BATH$1,2002521 Caper Ln Unit 203
2521 Caper Ln, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,565
1418 Beatrice Dr
1418 Beatrice Dr, Orlando, FL 32810 -
2 BEDS, 2 BATHS$1,900
411 Poplar Ct
411 Poplar Ct, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,890
4435 Fairview Ave
4435 Fairview Ave, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,6004418 Eli St
4418 Eli St, Orlando, FL 32804 -
3 BEDS, 1.5 BATHS$1,995776 Carew Ave
776 Carew Ave, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,290
64 Taylor Ave
64 Taylor Ave, Eatonville, FL 32751 -
2 BEDS, 1 BATH$1,650
1425 Virginia Dr
1425 Virginia Dr, Orlando, FL 32803 -
1 BED, 1 BATH$1,200
2517 Caper Ln Unit 205
2517 Caper Ln, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,6005314 Andrus Ave
5314 Andrus Ave, Orlando, FL 32810 -
2 BEDS, 2 BATHS$1,6005532 Charleston St
5532 Charleston St, Orlando, FL 32807 -
1 BED, 1 BATH$1,000
421 E KENNEDY Blvd
421 E KENNEDY Blvd, EATONVILLE, FL 32751 -
2 BEDS, 1 BATH$1,925
2512 Musselwhite Ave Unit #1
2512 Musselwhite Ave, Orlando, FL 32804 -
1 BED, 1 BATH$1,450
2512 Musselwhite Ave Unit 3
2512 Musselwhite Ave, Orlando, FL 32804 -
3 BEDS, 2 BATHS$1,800404 Banyon Tree Cir Unit 200
404 Banyon Tree Cir, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,400550 Flemming Way Unit 200
550 Flemming Way, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,400
496 Banyon Tree Cir Unit 104
496 Banyon Tree Cir, Maitland, FL 32751
Showing 42 of 179 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 539 Sq Ft $1,358 / mo
- 1 Bedroom 707 Sq Ft $1,455 / mo
- 2 Bedrooms 1,019 Sq Ft $1,733 / mo
- 3 Bedrooms 1,273 Sq Ft $2,030 / mo
- 4 Bedrooms 1,506 Sq Ft $1,540 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Winter Park Woods 761 Sq Ft $1,378/mo
- Four Seasons 606 Sq Ft $1,391/mo
- Winter Park Pines Merrie Oaks 606 Sq Ft $1,391/mo
- Laurel Springs 743 Sq Ft $1,392/mo
- Winter Park Pines 674 Sq Ft $1,431/mo
- Eastbrook 744 Sq Ft $1,442/mo
- Lake Howell 747 Sq Ft $1,511/mo
- Villas of Casselberry 759 Sq Ft $1,511/mo
- Cedarwood Village 653 Sq Ft $1,530/mo
- Windward Square 779 Sq Ft $1,538/mo
Getting Around Winter Park
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About Our Deals
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Note: Based on community-supplied data and independent market research. Subject to change without notice.