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Condos for Rent under $2,000 in Winter Park FL - 843 Rentals

7765 Country Pl

7765 Country Pl, Winter Park, FL 32792
1 / 5
$1,850

3 Beds, 2 Baths, 1,230 sq ft

Pool

(877) 300-6995
7309 Daniel Webster Dr Unit Apt A

7309 Daniel Webster Dr, Winter Park, FL 32792
1 / 17
$1,050

Studio, 1 Bath, 597 sq ft

(321) 353-7200
2337 Inagua Way

2337 Inagua Way, Winter Park, FL 32792
1 / 5
$950

1 Bed, 1 Bath

Pets Allowed Pool Furnished Hardwood Floors Fenced Lot Security System Vaulted Ceiling

(401) 207-9079
2407 Branch Way Unit 107 Maitland, FL

2407 Branch Way Unit 107 Maitland, FL, Maitland, FL 32751
1 / 5
$1,750

2 Beds, 1 Bath

Pets Allowed Pool Fitness Center

(786) 460-0355
851 Miles Ave Unit Aragón Condominum

851 Miles Ave Unit Aragón Condominum, Winter Park, FL 32789
1 / 17
$1,550

2 Beds, 1 Bath, 808 sq ft

Pool Smoke Free

(321) 461-2575
783 Formosa Ave Unit B2

783 Formosa Ave Unit B2, Winter Park, FL 32789

For Rent

By Owner
1 / 5
$1,100

1 Bed, 1 Bath, 500 sq ft

Patio Smoke Free High Ceilings
169 Lewfield Cir Unit 169

169 Lewfield Cir Unit 169, Winter Park, FL 32792
1 / 5
$1,450

1 Bed, 1 Bath, 678 sq ft

Pets Allowed

(407) 467-6379
1250 S Denning Dr Unit 130

1250 S Denning Dr Unit 130, Winter Park, FL 32789
1 / 5
$1,750

2 Beds, 2 Baths, 913 sq ft

Pets Allowed

(407) 731-9938
3069 Aaron Burr Ave Unit D

3069 Aaron Burr Ave Unit D, Winter Park, FL 32792
1 / 5
$1,200

1 Bed, 1 Bath, 537 sq ft

Pets Allowed

(407) 721-3829
1695 Lee Rd Unit C103

1695 Lee Rd Unit C103, Winter Park, FL 32789
1 / 5
$1,600

2 Beds, 1 Bath, 881 sq ft

Pets Allowed

(407) 948-5347
2500 Lee Rd Unit 213

2500 Lee Rd Unit 213, Winter Park, FL 32789
1 / 7
$1,450

2 Beds, 1 Bath, 851 sq ft

Pool

(321) 732-8854
1695 Lee Rd Unit C204

1695 Lee Rd Unit C204, Winter Park, FL 32789
1 / 5
$1,349

2 Beds, 1 Bath, 881 sq ft

(407) 207-2220
7268 Swallow Run Unit 7268

7268 Swallow Run Unit 7268, Winter Park, FL 32792
1 / 5
$1,600

2 Beds, 2 Baths, 784 sq ft

(407) 738-1680
2500 Lee Rd Unit 222

2500 Lee Rd Unit 222, Winter Park, FL 32789
1 / 5
$1,375

1 Bed, 1 Bath, 645 sq ft

Furnished Waterfront

(904) 907-5440
3035 George Mason Ave Unit 20B

3035 George Mason Ave Unit 20B, Winter Park, FL 32792
1 / 5
$1,375

1 Bed, 1 Bath, 549 sq ft

(407) 749-4157
1000 S Semoran Blvd Unit S

1000 S Semoran Blvd Unit S, Winter Park, FL 32792
1 / 5
$1,675

2 Beds, 2 Baths, 1,003 sq ft

(321) 239-8509
200 St Andrews Blvd Unit 2307

200 St Andrews Blvd Unit 2307, Winter Park, FL 32792
1 / 5
$1,600

2 Beds, 2 Baths, 1,119 sq ft

Pets Allowed

(407) 463-7973
186 Scottsdale Square Unit 186

186 Scottsdale Square Unit 186, Winter Park, FL 32792
1 / 5
$1,700

2 Beds, 2 Baths, 1,020 sq ft

Pets Allowed

(321) 947-0424
7340 Swallow Run Unit 7340

7340 Swallow Run Unit 7340, Winter Park, FL 32792
1 / 5
$1,575

2 Beds, 2 Baths, 802 sq ft

Pets Allowed

(321) 946-1119
261 Scottsdale Square Unit 261

261 Scottsdale Square Unit 261, Winter Park, FL 32792
1 / 5
$1,245

1 Bed, 1 Bath, 756 sq ft

Pets Allowed

(407) 860-3803
1000 S Semoran Blvd Unit 816

1000 S Semoran Blvd Unit 816, Winter Park, FL 32792
1 / 5
$1,500

2 Beds, 2 Baths, 1,049 sq ft

Pets Allowed

(407) 879-0720
1000 S Semoran Blvd Unit 606

1000 S Semoran Blvd Unit 606, Winter Park, FL 32792
1 / 5
$1,650

2 Beds, 2 Baths, 1,049 sq ft

Pets Allowed

(407) 963-6577
7794 Country Pl Unit 7794

7794 Country Pl Unit 7794, Winter Park, FL 32792
1 / 5
$1,575

2 Beds, 2 Baths, 1,068 sq ft

Pets Allowed

(407) 925-4760
2520 Caper Ln Unit 102

2520 Caper Ln Unit 102, Maitland, FL 32751

For Rent

By Owner
1 / 11
$1,300

1 Bed, 1 Bath, 759 sq ft

Pool Walk-In Closets Smoke Free Fitness Center

(321) 352-3506
4280 Upper Union Rd Unit Garage

4280 Upper Union Rd Unit Garage, Orlando, FL 32814
1 / 5
$1,875

1 Bed, 1 Bath, 627 sq ft

(407) 415-2315
2515 Formosa Ave Unit 2515 Formosa Ave

2515 Formosa Ave Unit 2515 Formosa Ave, Orlando, FL 32804

For Rent

By Owner
1 / 26
$1,700

2 Beds, 1 Bath, 850 sq ft

Smoke Free

(321) 352-3336
555 Flemming Way Unit 201

555 Flemming Way Unit 201, Maitland, FL 32751
1 / 5
$1,150

1 Bed, 1 Bath, 550 sq ft

(407) 879-0720
2407 Branch Way Unit 107

2407 Branch Way Unit 107, Maitland, FL 32751
1 / 5
$1,700

2 Beds, 1 Bath, 1,051 sq ft

(813) 720-7480
2512 Musselwhite Ave Unit 3

2512 Musselwhite Ave Unit 3, Orlando, FL 32804
1 / 5
$1,450

1 Bed, 1 Bath, 450 sq ft

Pets Allowed Furnished

(321) 947-7481
$850

2 Beds, 2 Baths, 1,004 sq ft

1000 S Semoran Blvd Unit 820, Winter Park, FL 32792
$1,220

1 Bed, 1 Bath, 656 sq ft

3035 George Mason Ave, Winter Park, FL 32792
$1,349

2 Beds, 1 Bath, 881 sq ft

1695 Lee Rd Unit C204, Winter Park, FL 32789
$1,450

2 Beds, 1 Bath, 851 sq ft

2500 Lee Rd Unit 213, Winter Park, FL 32789
$1,500

2 Beds, 2 Baths, 1,049 sq ft

1000 S Semoran Blvd, Winter Park, FL 32792
$1,600

2 Beds, 1 Bath, 881 sq ft

1695 Lee Rd Unit # D211, Winter Park, FL 32789
$1,575

2 Beds, 2 Baths

7340 Swallow Run, Winter Park, FL 32792
$1,895

3 Beds, 2 Baths, 1,149 sq ft

1695 Lee Rd Unit D215, Winter Park, FL 32789
$1,595

2 Beds, 2 Baths, 1,045 sq ft

1000 S Semoran Blvd Unit 806, Winter Park, FL 32792
$1,700

2 Beds, 2 Baths, 1,059 sq ft

4968 Tangerine Ave Unit 4968, Winter Park, FL 32792
$1,995

2 Beds, 2.5 Baths, 1,611 sq ft

7474 Canford Ct Unit 13, Winter Park, FL 32792
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Winter Park, FL Condos for Rent Under $2,000

Search for condos for rent in Winter Park, FL on Apartments.com. With 843 available, you can find the right condo with the floor plan and amenities that fit your needs. Many condo rentals are pet friendly and furnished to fit renters' lifestyles. When you rent a condo, you’ll likely rent from an individual owner rather than a property management company. This means units in the same building may have different features and layouts. Be sure to check out the photos and take a tour of the unit as you search for your Winter Park home. There are some terrific Winter Park neighborhoods with condos for rent, including Eastside, Downtown Orlando and South Orlando. While the average rent for a condo in Winter Park is $1,632, prices can vary by location, ranging anywhere from $850 to $3,000. If you’re looking for a budget-friendly condo to rent, try looking in affordable nearby cities like Maitland, Fairview Shores and Eatonville.