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Condos for Rent under $2,000 in Winter Park FL - 846 Rentals

7309 Daniel Webster Dr Unit Apt A

7309 Daniel Webster Dr, Winter Park, FL 32792
1 / 17
$1,000

Studio, 1 Bath, 597 sq ft
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 / 19
$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
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
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
1695 Lee Rd Unit C204

1695 Lee Rd Unit C204, Winter Park, FL 32789
1 / 5
$1,299

2 Beds, 1 Bath, 881 sq ft
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
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
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
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
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
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
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
1000 S Semoran Blvd Unit 606

1000 S Semoran Blvd Unit 606, Winter Park, FL 32792
1 / 5
$1,500

2 Beds, 2 Baths, 1,049 sq ft

Pets Allowed
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
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
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
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
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
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
555 Flemming Way Unit 201

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

1 Bed, 1 Bath, 550 sq ft
$850

2 Beds, 2 Baths, 1,004 sq ft

Room for Rent

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
$1,575

2 Beds, 2 Baths

7340 Swallow Run, Winter Park, FL 32792
$1,450

2 Beds, 1 Bath, 851 sq ft

2500 Lee Rd Unit 213, Winter Park, FL 32789
$1,795

3 Beds, 2 Baths, 1,149 sq ft

1695 Lee Rd Unit D215, Winter Park, FL 32789
$1,750

2 Beds, 2 Baths, 1,018 sq ft

2941 Antique Oaks Cir Unit 77, Winter Park, FL 32792
$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
$1,695

2 Beds, 2.5 Baths, 1,611 sq ft

7474 Canford Ct Unit 13, Winter Park, FL 32792
$1,450

1 Bed, 1 Bath, 749 sq ft

3037 Antique Oaks Cir Unit 158, Winter Park, FL 32792
$1,650

2 Beds, 2 Baths, 1,206 sq ft

440 Banyon Tree Cir, Maitland, FL 32751
$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 846 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 $1,593, 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.