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Condos for Rent under $2,000 in Winter Park FL - 967 Rentals

5335 Andrus Ave

5335 Andrus Ave, Orlando, FL 32810
1 / 5
$1,795

2 Beds, 1 Bath, 750 sq ft

Fenced Lot
2407 Branch Way Unit 107 Maitland, FL

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

2 Beds, 1 Bath

Pets Allowed Pool Fitness Center
10 East St

10 East St, Eatonville, FL 32751
1 / 18
$1,295

1 Bed, 1 Bath, 1,000 sq ft
5530 Old Cheney Hwy Unit Apartment 3

5530 Old Cheney Hwy Unit Apartment 3, Orlando, FL 32807
1 / 5
$600

1 Bed, 1 Bath

Furnished Security System
2407 Branch Way

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

2 Beds, 1 Bath

Pets Allowed Pool Fitness Center
1695 Lee Rd Unit # C-214

1695 Lee Rd Unit # C-214, Winter Park, FL 32789
1 / 10
$1,600

2 Beds, 1 Bath, 1,078 sq ft

Pets Allowed Balcony Smoke Free
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
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
200 St Andrews Blvd Unit 2108

200 St Andrews Blvd Unit 2108, Winter Park, FL 32792
1 / 5
$1,895

2 Beds, 2 Baths, 1,119 sq ft

Pets Allowed
300 Scottsdale Square Unit 300

300 Scottsdale Square Unit 300, Winter Park, FL 32792
1 / 5
$1,995

2 Beds, 1.5 Baths, 1,085 sq ft
3212 Netherwood Dr

3212 Netherwood Dr, Winter Park, FL 32792
1 / 5
$1,200

Studio, 1 Bath, 280 sq ft
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
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
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
293 Scottsdale Square Unit 293

293 Scottsdale Square Unit 293, Winter Park, FL 32792
1 / 5
$1,250

1 Bed, 1 Bath, 785 sq ft

Pets Allowed
3035 George Mason Ave Unit 20D

3035 George Mason Ave Unit 20D, Winter Park, FL 32792
1 / 5
$1,350

1 Bed, 1 Bath, 549 sq ft
1000 S Semoran Blvd Unit 813

1000 S Semoran Blvd Unit 813, Winter Park, FL 32792
1 / 5
$1,800

2 Beds, 2 Baths, 1,003 sq ft

Pets Allowed
7340 Swallow Run Unit 7340

7340 Swallow Run Unit 7340, Winter Park, FL 32792
1 / 5
$1,550

2 Beds, 2 Baths, 802 sq ft

Pets Allowed
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
3212 Netherwood Dr

3212 Netherwood Dr, Winter Park, FL 32792
1 / 5
$1,500

1 Bed, 1 Bath, 400 sq ft
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
555 Flemming Way Unit 201

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

1 Bed, 1 Bath, 550 sq ft
5517 Decatur St Unit 5517

5517 Decatur St Unit 5517, Orlando, FL 32807
1 / 5
$1,575

2 Beds, 1.5 Baths, 996 sq ft

Pets Allowed
421 E Kennedy Blvd

421 E Kennedy Blvd, Eatonville, FL 32751
1 / 2
$1,000

1 Bed, 1 Bath, 450 sq ft

Cats Allowed
2407 Branch Way Unit 107

2407 Branch Way Unit 107, Maitland, FL 32751
1 / 5
$1,600

2 Beds, 1 Bath, 1,051 sq ft

Pets Allowed
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
2407 Branch Way Unit 205

2407 Branch Way Unit 205, Maitland, FL 32751
1 / 5
$1,700

2 Beds, 1 Bath, 1,051 sq ft
$1,175

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
$1,550

2 Beds, 2 Baths

7340 Swallow Run, Winter Park, FL 32792
$1,500

2 Beds, 2 Baths, 1,049 sq ft

1000 S Semoran Blvd, Winter Park, FL 32792
$1,450

1 Bed, 1 Bath, 749 sq ft

3037 Antique Oaks Cir Unit 158, Winter Park, FL 32792
$1,749

3 Beds, 2 Baths, 1,149 sq ft

1695 Lee Rd Unit D215, Winter Park, FL 32789
$1,725

2 Beds, 2 Baths, 1,018 sq ft

2941 Antique Oaks Cir Unit 77, Winter Park, FL 32792
$1,550

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
$2,000

3 Beds, 2.5 Baths, 1,720 sq ft

2463 Grand Teton Cir, Winter Park, FL 32792
$1,399

1 Bed, 1 Bath, 727 sq ft

200 St Andrews Blvd Unit 401, Winter Park, FL 32792
$1,475

1 Bed, 1 Bath, 663 sq ft

2920 Plaza Terrace Dr, Orlando, FL 32803
$1,595

2 Beds, 2 Baths, 850 sq ft

35 E Winter Park St Unit 35A, Orlando, FL 32804
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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 967 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 $1,673, prices can vary by location, ranging anywhere from $1,000 to $4,500. If you’re looking for a budget-friendly condo to rent, try looking in affordable nearby cities like Maitland, Fairview Shores and Aloma.