Condos for Rent under $2,000 in Winter Park FL - 804 Rentals

2667 Cayman Way

2667 Cayman Way, Winter Park, FL 32792
1 / 5
$1,800

3 Beds, 2 Baths, 1,274 sq ft

Pets Allowed

(407) 690-9406
3057 Aaron Burr Ave Unit 2

3057 Aaron Burr Ave Unit 2, Winter Park, FL 32792
1 / 5
$1,600

2 Beds, 2 Baths, 1,066 sq ft

Pets Allowed Pool Walk-In Closets

(321) 472-2528
476 Banyon Tree Cir Unit 202

476 Banyon Tree Cir Unit 202, Maitland, FL 32751
1 / 5
$1,150

1 Bed, 1 Bath, 757 sq ft

Pets Allowed Pool Fitness Center

(407) 463-5235
2037 Linden Rd Unit 2037 linden rd B

2037 Linden Rd Unit 2037 linden rd B, Winter Park, FL 32792
1 / 13
$1,200

1 Bed, 1 Bath, 650 sq ft

Cats Allowed Smoke Free

(321) 340-6548
1250 S Denning Dr Unit 136

1250 S Denning Dr Unit 136, Winter Park, FL 32789
1 / 21
$1,325

1 Bed, 1 Bath, 513 sq ft

Pool Furnished Smoke Free

(321) 321-5450
2137 Oglesby Ave Unit A2

2137 Oglesby Ave Unit A2, Winter Park, FL 32789
1 / 8
$799

1 Bed, 1 Bath, 250 sq ft

Smoke Free
1000 S Semoran Blvd Unit S

1000 S Semoran Blvd Unit S, Winter Park, FL 32792
1 / 5
$1,250

1 Bed, 1 Bath, 735 sq ft

Pool Walk-In Closets Fireplace Smoke Free

(321) 939-3748
7457 Daniel Webster Dr Unit D

7457 Daniel Webster Dr Unit D, Winter Park, FL 32792
1 / 12
$1,200

1 Bed, 1 Bath, 559 sq ft

Pets Allowed Pool

(321) 320-8278
631 Saint Johns Ct Unit #631

631 Saint Johns Ct Unit #631, Winter Park, FL 32792
1 / 5
$1,499

1 Bed, 1 Bath, 759 sq ft

Pool Fireplace Smoke Free Fitness Center Wheelchair Accessible

(727) 353-8479
151 N Orlando Ave Unit 229

151 N Orlando Ave Unit 229, Winter Park, FL 32789
1 / 5
$1,849

2 Beds, 1 Bath, 710 sq ft

Dogs Allowed Waterfront

(407) 257-9737
3008 Antique Oaks Cir Unit 106

3008 Antique Oaks Cir Unit 106, Winter Park, FL 32792
1 / 5
$1,295

1 Bed, 1 Bath, 749 sq ft

Pets Allowed

(407) 897-3366
169 Lewfield Cir Unit 169

169 Lewfield Cir Unit 169, Winter Park, FL 32792
1 / 5
$1,550

1 Bed, 1 Bath, 678 sq ft

Pets Allowed

(407) 467-6379
1000 S Semoran Blvd Unit S

1000 S Semoran Blvd Unit S, Winter Park, FL 32792
1 / 5
$1,250

1 Bed, 1 Bath, 735 sq ft

(407) 502-9420
2500 Lee Rd Unit 213

2500 Lee Rd Unit 213, Winter Park, FL 32789
1 / 16
$1,600

2 Beds, 1 Bath, 851 sq ft

Pool

(321) 732-8854
3651 N Goldenrod Rd Unit 102

3651 N Goldenrod Rd Unit 102, Winter Park, FL 32792
1 / 5
$1,800

2 Beds, 2 Baths, 840 sq ft

Dogs Allowed Furnished

(407) 580-1193
200 St Andrews Blvd Unit 2008

200 St Andrews Blvd Unit 2008, Winter Park, FL 32792
1 / 5
$1,600

2 Beds, 2 Baths, 1,119 sq ft

(407) 431-0991
627 Grenadine Ct Unit S

627 Grenadine Ct Unit S, Winter Park, FL 32792
1 / 5
$1,695

2 Beds, 2 Baths, 1,037 sq ft

Pets Allowed

(321) 363-6345
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
151 N Orlando Ave Unit 118

151 N Orlando Ave Unit 118, Winter Park, FL 32789
1 / 5
$1,800

2 Beds, 1 Bath, 710 sq ft

(407) 654-9992
1695 Lee Rd Unit C204

1695 Lee Rd Unit C204, Winter Park, FL 32789
1 / 5
$1,399

2 Beds, 1 Bath, 881 sq ft

(407) 207-2220
1250 S Denning Dr Unit 205

1250 S Denning Dr Unit 205, Winter Park, FL 32789
1 / 5
$1,800

2 Beds, 2 Baths, 908 sq ft

(407) 501-0055
2500 Lee Rd Unit 222

2500 Lee Rd Unit 222, Winter Park, FL 32789
1 / 5
$2,000

1 Bed, 1 Bath, 645 sq ft

Furnished Waterfront

(904) 907-5440
200 St Andrews Blvd Unit 2307

200 St Andrews Blvd Unit 2307, Winter Park, FL 32792
1 / 5
$1,700

2 Beds, 2 Baths, 1,119 sq ft

Pets Allowed

(407) 463-7973
851 Miles Ave Unit 15

851 Miles Ave Unit 15, Winter Park, FL 32789
1 / 5
$1,695

2 Beds, 1 Bath, 808 sq ft

Pets Allowed

(321) 246-7930
4866 Tangerine Ave Unit 4866

4866 Tangerine Ave Unit 4866, Winter Park, FL 32792
1 / 5
$1,700

2 Beds, 2 Baths, 1,059 sq ft

Pets Allowed

(407) 406-5300
3651 N Goldenrod Rd Unit F210

3651 N Goldenrod Rd Unit F210, Winter Park, FL 32792
1 / 5
$1,500

2 Beds, 2 Baths, 840 sq ft

Pets Allowed

(407) 970-0579
200 St Andrews Blvd Unit 1403

200 St Andrews Blvd Unit 1403, Winter Park, FL 32792
1 / 5
$1,950

3 Beds, 2 Baths, 1,322 sq ft

Cats Allowed

(407) 883-2989
200 St Andrews Blvd Unit 906

200 St Andrews Blvd Unit 906, Winter Park, FL 32792
1 / 5
$1,550

1 Bed, 1 Bath, 727 sq ft

Cats Allowed

(407) 883-2989
1000 S Semoran Blvd Unit 811

1000 S Semoran Blvd Unit 811, Winter Park, FL 32792
1 / 5
$1,550

2 Beds, 2 Baths, 1,003 sq ft

Pets Allowed

(407) 868-2976
3057 Aaron Burr Ave Unit 3

3057 Aaron Burr Ave Unit 3, Winter Park, FL 32792
1 / 5
$1,300

1 Bed, 1 Bath, 803 sq ft

Pets Allowed

(407) 716-5435
7765 Country Pl

7765 Country Pl, Winter Park, FL 32792
1 / 5
$1,900

3 Beds, 2 Baths, 1,230 sq ft

(407) 551-3316
1000 S Semoran Blvd Unit 816

1000 S Semoran Blvd Unit 816, Winter Park, FL 32792
1 / 5
$1,550

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
2936 Antique Oaks Cir Unit 67

2936 Antique Oaks Cir Unit 67, Winter Park, FL 32792
1 / 5
$1,650

2 Beds, 2 Baths, 1,018 sq ft

Pets Allowed

(407) 948-5347
1695 Lee Rd Unit D113

1695 Lee Rd Unit D113, Winter Park, FL 32789
1 / 5
$1,500

2 Beds, 1 Bath, 881 sq ft

(407) 616-7700
424 Banyon Tree Cir Unit 102

424 Banyon Tree Cir Unit 102, Maitland, FL 32751
1 / 5
$1,595

2 Beds, 2 Baths, 1,206 sq ft

Pets Allowed

(407) 897-3366
2717 Stanfield Ave

2717 Stanfield Ave, Orlando, FL 32814
1 / 5
$1,500

Studio, 1 Bath, 592 sq ft

(423) 381-5701
2512 Musselwhite Ave Unit 2

2512 Musselwhite Ave Unit 2, Orlando, FL 32804
1 / 5
$1,395

1 Bed, 1 Bath, 450 sq ft

Pets Allowed Furnished

(321) 947-7481
951 Bennett Rd Unit 103

951 Bennett Rd Unit 103, Orlando, FL 32814
1 / 5
$1,699

1 Bed, 1 Bath, 958 sq ft

Pets Allowed

(813) 493-5383
5681 Charleston St Unit 55

5681 Charleston St Unit 55, Orlando, FL 32807
1 / 5
$1,650

3 Beds, 1.5 Baths, 1,133 sq ft

(407) 325-3593
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Condos Florida Orange County

Winter Park, FL Condos for Rent Under $2,000

Search for condos for rent in Winter Park, FL on Apartments.com. With 804 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 $1,861, prices can vary by location, ranging anywhere from $1,150 to $5,750. If you’re looking for a budget-friendly condo to rent, try looking in affordable nearby cities like Maitland, Fairview Shores and Eatonville.