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Winter Park FL Condos for Rent under $2,000

52 Rentals Available

2500 Lee Rd Unit 244

2500 Lee Rd Unit 244, Winter Park, FL 32789
1 / 5
1 Bed, 1 Bath, 645 sq ft

$1,465

Total Monthly Price

Total Monthly Price New

Prices include all required monthly fees.

Pool
2942 Antique Oaks Cir Unit 82

2942 Antique Oaks Cir, Winter Park, FL 32792
1 / 11
1 Bed

$1,380

Pets Allowed Pool
650 Trinidad Ct

650 Trinidad Ct, Winter Park, FL 32792
1 / 20
2 Beds

$1,745

Patio Fireplace
2500 Lee Rd Unit 212

2500 Lee Rd Unit 212, Winter Park, FL 32789

For Rent

By Owner
1 / 27
2 Beds, 1 Bath, 851 sq ft

$1,375

Total Monthly Price
12 Month Lease

Total Monthly Price New

Prices include all required monthly fees.

Pool Walk-In Closets Waterfront Smoke Free Clubhouse
1140 S Orlando Ave Unit Exeter E2

1140 S Orlando Ave Unit Exeter E2, Maitland, FL 32751
1 / 35
1 Bed, 1 Bath, 612 sq ft

$1,950

Total Monthly Price
12 Month Lease

Total Monthly Price New

Prices include all required monthly fees.

Pool Hardwood Floors Waterfront Wheelchair Accessible Clubhouse
2924 Antique Oaks Cir Unit 48

2924 Antique Oaks Cir Unit 48, Winter Park, FL 32792

For Rent

By Owner
1 / 6
2 Beds, 2.5 Baths, 1,100 sq ft

$1,850

Total Monthly Price
12 Month Lease

Total Monthly Price New

Prices include all required monthly fees.

Pets Allowed Pool Smoke Free
2520 Caper Ln Unit 102

2520 Caper Ln Unit 102, Maitland, FL 32751

For Rent

By Owner
1 / 10
1 Bed, 1 Bath, 759 sq ft

$1,300

Total Monthly Price
12 Month Lease

Total Monthly Price New

Prices include all required monthly fees.

Pool Walk-In Closets Smoke Free Fitness Center
627 Grenadine Ct Unit S

627 Grenadine Ct Unit S, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 1,037 sq ft

$1,695
1000 S Semoran Blvd Unit 115

1000 S Semoran Blvd Unit 115, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 1,003 sq ft

$1,400
1695 Lee Rd Unit B114

1695 Lee Rd Unit B114, Winter Park, FL 32789
1 / 5
2 Beds, 1 Bath, 881 sq ft

$1,500

Pets Allowed
3651 N Goldenrod Rd Unit B#104

3651 N Goldenrod Rd Unit B#104, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 840 sq ft

$1,350
200 St Andrews Blvd Unit 2903

200 St Andrews Blvd Unit 2903, Winter Park, FL 32792
1 / 5
2 Beds, 1.5 Baths, 1,219 sq ft

$1,850
3651 N Goldenrod Rd Unit C204

3651 N Goldenrod Rd Unit C204, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 840 sq ft

$1,395

Pets Allowed
1695 Lee Rd Unit C216

1695 Lee Rd Unit C216, Winter Park, FL 32789
1 / 5
3 Beds, 2 Baths, 1,149 sq ft

$1,650
3651 N Goldenrod Rd Unit C205

3651 N Goldenrod Rd Unit C205, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 840 sq ft

$1,575
651 Trinidad Ct Unit S

651 Trinidad Ct Unit S, Winter Park, FL 32792
1 / 5
1 Bed, 1 Bath, 759 sq ft

$1,450

Pets Allowed Fireplace
205 Lewfield Cir Unit 205

205 Lewfield Cir Unit 205, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 927 sq ft

$1,800

Pets Allowed Pool
3651 N Goldenrod Rd Unit 110

3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 840 sq ft

$1,450

Pets Allowed
1380 Indiana Ave Unit 3

1380 Indiana Ave Unit 3, Winter Park, FL 32789
1 / 5
2 Beds, 1 Bath, 920 sq ft

$1,495

Furnished
1695 Lee Rd Unit C110

1695 Lee Rd Unit C110, Winter Park, FL 32789
1 / 5
1 Bed, 1 Bath, 638 sq ft

$1,400

Pets Allowed
612 Montego Bay Ct Unit 612

612 Montego Bay Ct Unit 612, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 1,037 sq ft

$1,850

Cats Allowed
612 Trinidad Ct Unit 612

612 Trinidad Ct Unit 612, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 1,037 sq ft

$1,850

Pets Allowed Fireplace
200 St Andrews Blvd Unit 2302

200 St Andrews Blvd Unit 2302, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 987 sq ft

$1,750

Pets Allowed
7326 Swallow Run Unit 7326

7326 Swallow Run Unit 7326, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 800 sq ft

$1,500

Pets Allowed
2936 Antique Oaks Cir Unit 70

2936 Antique Oaks Cir Unit 70, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 1,018 sq ft

$1,650

Pets Allowed
2517 Caper Ln Unit 203

2517 Caper Ln Unit 203, Maitland, FL 32751
1 / 5
1 Bed, 1 Bath, 550 sq ft

$1,225

Pets Allowed
1162 Carmel Cir Unit 100

1162 Carmel Cir Unit 100, Casselberry, FL 32707
1 / 5
3 Beds, 2.5 Baths, 1,578 sq ft

$1,950

Pets Allowed Furnished
2517 Caper Ln Unit 205

2517 Caper Ln Unit 205, Maitland, FL 32751
1 / 5
1 Bed, 1 Bath, 550 sq ft

$1,200
400 Banyon Tree Cir Unit 102

400 Banyon Tree Cir Unit 102, Maitland, FL 32751
1 / 5
3 Beds, 2 Baths, 1,612 sq ft

$1,780
1159 Calle Del Norte Unit A

1159 Calle Del Norte Unit A, Casselberry, FL 32707
1 / 5
2 Beds, 2 Baths, 1,040 sq ft

$1,500

Pets Allowed Waterfront
1140 S Orlando Ave Unit E2

1140 S Orlando Ave Unit E2, Maitland, FL 32751
1 / 5
1 Bed, 1 Bath, 612 sq ft

$1,849

Pool Waterfront
492 Banyon Tree Cir Unit 206

492 Banyon Tree Cir Unit 206, Maitland, FL 32751
1 / 5
2 Beds, 1 Bath, 1,051 sq ft

$1,700
$1,024

2326 Wellington Blvd, Winter Park, FL 32789

1 Bed | 1 Bath | 755 sq ft
$1,700

4968 Tangerine Ave Unit 4968, Winter Park, FL 32792

2 Beds | 2 Baths | 1,059 sq ft
$1,545

200 St Andrews Blvd Unit 1803, Winter Park, FL 32792

2 Beds | 1.5 Baths | 1,219 sq ft
$1,345

2551 Medley Ct Unit 2551GEM, Winter Park, FL 32792

2 Beds | 2 Baths | 1,100 sq ft
$1,350

3651 N Goldenrod Rd Unit D101, Winter Park, FL 32792

2 Beds | 2 Baths | 840 sq ft
$1,450

3651 N Goldenrod Rd Unit Apt C110, Winter Park, FL 32792

2 Beds | 2 Baths | 840 sq ft
$1,495

3651 N Goldenrod Rd Unit Apartment E106, Winter Park, FL 32792

2 Beds | 2 Baths | 840 sq ft
$1,000

2517 Caper Ln Unit 207, Maitland, FL 32751

1 Bed | 1 Bath | 620 sq ft
Showing 40 of 52 Results - Page 1 of 2
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Condos Florida Orange County Winter Park

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

Search for condos for rent in Winter Park, FL on Apartments.com. With 52 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 Lawndale, Four Seasons and Winter Park DT Historic District. While the average rent for a condo in Winter Park is $1,979, prices can vary by location, ranging anywhere from $1,000 to $8,950. If you’re looking for a budget-friendly condo to rent, try looking in affordable nearby cities like Maitland, Fairview Shores and Eatonville.

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