Condos for Rent under $2,000 in Winter Park FL - 810 Rentals

1280 Vinings Ln Unit FL2-ID11A

1280 Vinings Ln Unit FL2-ID11A, Casselberry, FL 32707
1 / 5
$1,970

1 Bed, 1 Bath, 826 sq ft

Furnished Fitness Center

(972) 289-8633
851 Miles Ave Unit Aragón Condominum

851 Miles Ave Unit Aragón Condominum, Winter Park, FL 32789
1 / 17
$1,750

2 Beds, 1 Bath, 808 sq ft

Pool Smoke Free

(321) 461-2575
3651 N Goldenrod Rd

3651 N Goldenrod Rd, Winter Park, FL 32792
1 / 6
$1,800

2 Beds, 2 Baths, 1,000 sq ft

Pool Smoke Free

(321) 379-7624
940 W Fairbanks Ave Unit In-law apartment.

940 W Fairbanks Ave Unit In-law apartment., Orlando, FL 32804

For Rent

By Owner
1 / 10
$1,450

1 Bed, 1 Bath, 850 sq ft

Cats Allowed Furnished Smoke Free Lofts

(386) 282-5724
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
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
3651 N Goldenrod Rd Unit B102

3651 N Goldenrod Rd Unit B102, Winter Park, FL 32792
1 / 5
$1,800

2 Beds, 2 Baths, 840 sq ft

Dogs Allowed Furnished

(407) 580-1193
1695 Lee Rd Unit B102

1695 Lee Rd Unit B102, Winter Park, FL 32789
1 / 5
$1,950

3 Beds, 2 Baths, 1,149 sq ft

(407) 334-3417
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
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
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
$1,800

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
$1,600

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
$1,599

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
3651 N Goldenrod Rd Unit 104

3651 N Goldenrod Rd Unit 104, Winter Park, FL 32792
1 / 5
$1,600

2 Beds, 2 Baths, 840 sq ft

(407) 467-9411
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
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
3651 N Goldenrod Rd Unit 108

3651 N Goldenrod Rd Unit 108, Winter Park, FL 32792
1 / 5
$1,495

2 Beds, 2 Baths, 840 sq ft

Pets Allowed

(407) 733-8665
2500 Lee Rd Unit 213

2500 Lee Rd Unit 213, Winter Park, FL 32789
1 / 7
$1,595

2 Beds, 1 Bath, 851 sq ft

Pool

(321) 732-8854
559 Flemming Way Unit 101

559 Flemming Way Unit 101, Maitland, FL 32751
1 / 5
$1,175

1 Bed, 1 Bath, 550 sq ft

Pets Allowed

(407) 312-6472
2717 Stanfield Ave

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

Studio, 1 Bath, 592 sq ft

(423) 381-5701
421 E Kennedy Blvd

421 E Kennedy Blvd, Eatonville, FL 32751
1 / 2
$950

1 Bed, 1 Bath, 450 sq ft

Cats Allowed

(407) 579-1981
2407 Branch Way Unit 107

2407 Branch Way Unit 107, Maitland, FL 32751
1 / 5
$1,800

2 Beds, 1 Bath, 1,051 sq ft

(813) 720-7480
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
$800

1 Bed, 1 Bath

140 Stefanik Rd Unit Room 3, Winter Park, FL 32792
$1,250

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, 1,049 sq ft

1000 S Semoran Blvd, Winter Park, FL 32792
$2,000

2 Beds, 2 Baths, 1,120 sq ft

602 Trinidad Ct Unit 602, Winter Park, FL 32792
$1,995

3 Beds, 2 Baths, 1,149 sq ft

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

2 Beds, 2 Baths, 840 sq ft

3651 N Goldenrod Rd Unit A202, 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
$1,595

2 Beds, 1 Bath, 851 sq ft

2500 Lee Rd Unit 213, Winter Park, FL 32789
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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 810 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 $1,775, prices can vary by location, ranging anywhere from $950 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.