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Winter Park FL Condos for Rent under $2,000

60 Rentals Available

1500 Gay Rd Unit 25B

1500 Gay Rd Unit 25B, Winter Park, FL 32789
1 / 5
2 Beds, 2 Baths, 1,026 sq ft

$1,900

Total Monthly Price

Total Monthly Price New

Prices include all required monthly fees.

Pool Patio Walk-In Closets
1250 S Denning Dr

1250 S Denning Dr, Winter Park, FL 32789
1 / 8
2 Beds

$1,900

Pool

More Units at Mead Garden Condominiums
200 St Andrews Blvd Unit 316

200 St Andrews Blvd, Winter Park, FL 32792
1 / 13
1 Bed

$1,625

Pets Allowed Pool Tennis Court Fitness Center
659 Montego Bay Ct

659 Montego Bay Ct, Winter Park, FL 32792
1 / 20
2 Beds

$1,695

Pets Allowed Pool Basketball Court Tennis Court Fitness Center Clubhouse
551 Flemming Way Unit 201

551 Flemming Way Unit 201, Maitland, FL 32751
1 / 5
1 Bed, 1 Bath, 550 sq ft

$1,150

Total Monthly Price

Total Monthly Price New

Prices include all required monthly fees.

Pool Walk-In Closets Fitness Center
452 Banyon Tree Cir Unit 200

452 Banyon Tree Cir Unit 200, Maitland, FL 32751
1 / 5
1 Bed, 1 Bath, 550 sq ft

$1,125

Total Monthly Price

Total Monthly Price New

Prices include all required monthly fees.

Pool Walk-In Closets Fitness Center
2422 Branch Way Unit 104

2422 Branch Way, Maitland, FL 32751
1 / 5
1 Bed

$1,050

Pool
821 Mulberry St Unit D

821 Mulberry St, Maitland, FL 32751
1 / 12
2 Beds

$2,000
5301 Andrus Ave

5301 Andrus Ave, Orlando, FL 32810
1 / 3
2 Beds

$1,600

Pets Allowed
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
1172 Calle Del Rey Unit A

1172 Calle Del Rey Unit A, Casselberry, FL 32707

For Rent

By Owner
1 / 28
2 Beds, 2 Baths, 1,040 sq ft

$1,600

Total Monthly Price
12 Month Lease

Total Monthly Price New

Prices include all required monthly fees.

Pool Patio
200 Saint Andrews Blvd

200 Saint Andrews Blvd, Winter Park, FL 32792

For Rent

By Owner
1 / 42
1 Bed

$1,550

3 Beds

$1,950

Total Monthly Price
12 Month Lease

Total Monthly Price New

Prices include all required monthly fees.

Pool Balcony Walk-In Closets Smoke Free Fitness Center Wheelchair Accessible Clubhouse
2918 Antique Oaks Cir Unit 25

2918 Antique Oaks Cir Unit 25, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 1,018 sq ft

$1,595

Dogs Allowed
3651 N Goldenrod Rd Unit C201

3651 N Goldenrod Rd Unit C201, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 840 sq ft

$1,395

Pets Allowed
205 Lewfield Cir Unit 205

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

$1,700

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
1695 Lee Rd Unit B204

1695 Lee Rd Unit B204, Winter Park, FL 32789
1 / 5
2 Beds, 1 Bath, 881 sq ft

$1,500

Pets Allowed
1695 Lee Rd Unit A101

1695 Lee Rd Unit A101, Winter Park, FL 32789
1 / 5
3 Beds, 2 Baths, 1,149 sq ft

$1,650

Pets Allowed
1000 S Semoran Blvd Unit 715

1000 S Semoran Blvd Unit 715, Winter Park, FL 32792
1 / 5
1 Bed, 1 Bath, 735 sq ft

$1,150

Pets Allowed
1695 Lee Rd Unit C103

1695 Lee Rd Unit C103, Winter Park, FL 32789
1 / 5
2 Beds, 1 Bath, 881 sq ft

$1,600

Pets Allowed
2449 Grand Teton Cir Unit 2449

2449 Grand Teton Cir Unit 2449, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 1,457 sq ft

$2,000

Fireplace
612 Trinidad Ct Unit 612

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

$1,750

Cats Allowed Fireplace
1695 Lee Rd Unit E215

1695 Lee Rd Unit E215, Winter Park, FL 32789
1 / 5
3 Beds, 2 Baths, 1,149 sq ft

$1,850

Pets Allowed
3370 Cedar Springs Pl Unit 156

3370 Cedar Springs Pl Unit 156, Winter Park, FL 32792
1 / 5
2 Beds, 2.5 Baths, 1,031 sq ft

$1,625

Pets Allowed
1000 S Semoran Blvd Unit 305

1000 S Semoran Blvd Unit 305, Winter Park, FL 32792
1 / 5
1 Bed, 1 Bath, 735 sq ft

$1,195

Pets Allowed
7338 Swallow Run Unit 7338

7338 Swallow Run Unit 7338, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 774 sq ft

$1,600
3068 Autumn Ct Unit na

3068 Autumn Ct Unit na, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 1,038 sq ft

$1,640

Pets Allowed
2481 Tahoe Cir Unit 2481

2481 Tahoe Cir Unit 2481, Winter Park, FL 32792
1 / 5
2 Beds, 2.5 Baths, 1,495 sq ft

$1,850

Fireplace
7336 Forest Hill Ct Unit 240

7336 Forest Hill Ct Unit 240, Winter Park, FL 32792
1 / 5
2 Beds, 1.5 Baths, 990 sq ft

$1,700

Pets Allowed
1695 Lee Rd Unit A113

1695 Lee Rd Unit A113, Winter Park, FL 32789
1 / 5
2 Beds, 1 Bath, 881 sq ft

$1,600

Pets Allowed
3651 N Goldenrod Rd Unit A103

3651 N Goldenrod Rd Unit A103, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 840 sq ft

$1,600

Pets Allowed
3367 Riverview Way Unit 450

3367 Riverview Way Unit 450, Winter Park, FL 32792
1 / 5
3 Beds, 2.5 Baths, 1,151 sq ft

$1,800

Pets Allowed
2075 Howell Branch Rd Unit 101

2075 Howell Branch Rd Unit 101, Maitland, FL 32751
1 / 5
2 Beds, 1 Bath, 875 sq ft

$1,175
4328 Edgewater Dr Unit E104

4328 Edgewater Dr Unit E104, Orlando, FL 32804
1 / 5
1 Bed, 1 Bath, 628 sq ft

$1,550
$1,700

4968 Tangerine Ave Unit 4968, Winter Park, FL 32792

2 Beds | 2 Baths | 1,059 sq ft
$1,400

1855 Eastbrook Blvd Unit 1, Winter Park, FL 32792

1 Bed | 1 Bath | 600 sq ft
$1,375

1000 S Semoran Blvd Unit 806, Winter Park, FL 32792

2 Beds | 2 Baths | 1,045 sq ft
$1,450

1695 Lee Rd Unit Apartment A103, Winter Park, FL 32789

2 Beds | 1 Bath | 881 sq ft
$1,300

3004 George Mason Ave Unit K5d, Winter Park, FL 32792

2 Beds | 2.5 Baths | 1,079 sq ft
$1,650

2404 Gallery View Dr, Winter Park, FL 32792

2 Beds | 2 Baths | 902 sq ft
Showing 40 of 59 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 60 available, you can find the right condo with the floor plan and amenities that fit your needs. 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.

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