Condos for Rent in Oakcrest - Winter Park

3,227 Rentals

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400 E Colonial Dr Unit 1201

400 E Colonial Dr Unit 1201, Orlando, FL 32803
1 / 27
$1,875

1 Bed, 1 Bath, 788 sq ft

Pool Balcony Gated Smoke Free Fitness Center Den Double Vanities
1610 N Goldenrod Rd Unit ID1094191P

1610 N Goldenrod Rd, Orlando, FL 32807
1 / 16
3 Beds

$4,258

Pets Allowed Furnished Garden
1629 N Goldenrod Rd Unit ID1094202P

1629 N Goldenrod Rd, Azalea Park, FL 32807
1 / 20
4 Beds

$4,209

Pets Allowed Balcony Furnished Garden
1735 Grayson Dr Unit ID1094204P

1735 Grayson Dr, Orlando, FL 32825
1 / 5
2 Beds

$3,239

Pets Allowed Furnished
1731 Grayson Dr Unit ID1094212P

1731 Grayson Dr Unit ID1094212P, Orlando, FL 32825
1 / 5
Studio

$2,375

Pets Allowed Furnished Garden
1711 Asher Ln Unit ID1094225P

1711 Asher Ln Unit ID1094225P, Orlando, FL 32803
1 / 5
3 Beds

$4,161

Pets Allowed Balcony Furnished Garden
1422 Dauphin Ln Unit ID1094223P

1422 Dauphin Ln Unit ID1094223P, Orlando, FL 32803
1 / 5
2 Beds

$4,229

Pets Allowed Furnished
2667 Rook Cv Unit 2667 Rook Cove

2667 Rook Cv, Winter Park, FL 32792
1 / 20
2 Beds

$1,795

Pets Allowed Fenced Lot
210 Magnolia Rd Unit 104

210 Magnolia Rd, Maitland, FL 32751

1 / 13

2 Beds

$2,050
200 Maitland Ave Unit 45

200 Maitland Ave, Altamonte Springs, FL 32701

1 / 12

1 Bed

$1,250
5530 Old Cheney Hwy Unit Apartment 3

5530 Old Cheney Hwy, Orlando, FL 32807
1 / 5
1 Bed

$650

Furnished Security System
1731 Grayson Dr Unit ID1094207P

1731 Grayson Dr, Orlando, FL 32825

1 / 10

1 Bed

$2,645
9096 Dubois Blvd Unit ID1094220P

9096 Dubois Blvd, Orlando, FL 32825
1 / 20
3 Beds

$4,645

Pets Allowed Balcony Furnished Fireplace Garden
210 Magnolia Rd Unit 206

210 Magnolia Rd, Maitland, FL 32751
1 / 20
3 Beds

$2,275

Dogs Allowed Pool Hardwood Floors Fireplace
3060 George Mason Ave Unit 10

3060 George Mason Ave Unit 10, Winter Park, FL 32792
1 / 5
1 Bed, 1 Bath, 803 sq ft

$1,300
1500 Gay Rd Unit Apt 3B

1500 Gay Rd, Winter Park, FL 32789
1 / 20
2 Beds

$1,750
5530 Old Cheney Hwy Unit 2

5530 Old Cheney Hwy, Orlando, FL 32807
1 / 4
1 Bed

$780

Furnished
1950 Summer Club Dr Unit 202

1950 Summer Club Dr Unit 202, Oviedo, FL 32765
1 / 5
3 Beds, 2 Baths, 1,180 sq ft

$2,000

Dogs Allowed Pool Patio Walk-In Closets Deck
600 Northern Way Unit 1005

600 Northern Way Unit 1005, Winter Springs, FL 32708

For Rent

By Owner
1 / 74
3 Beds, 3 Baths, 1,700 sq ft

$2,095

Pool Patio Hardwood Floors Yard Gated Island Kitchen Smoke Free
160 Reserve Cir

160 Reserve Cir, Oviedo, FL 32765

For Rent

By Owner
1 / 8
1 Bed, 1 Bath, 1,098 sq ft

$1,100

Room for Rent

Pool Balcony Furnished Smoke Free Basketball Court Fitness Center
2918 Antique Oaks Cir Unit #31

2918 Antique Oaks Cir Unit #31, Winter Park, FL 32792

For Rent

By Owner
1 / 46
2 Beds, 2 Baths, 1,018 sq ft

$1,900

Pets Allowed Pool Balcony Furnished Patio Walk-In Closets Smoke Free
1902 Park Manor Dr Unit 1902 Park Manor Dr

1902 Park Manor Dr Unit 1902 Park Manor Dr, Orlando, FL 32817

For Rent

By Owner
1 / 8
2 Beds

$1,445

Dogs Allowed Smoke Free Fitness Center
445 Shine Ave Unit A

445 Shine Ave Unit A, Orlando, FL 32803
1 / 5
1 Bed, 1 Bath, 544 sq ft

$1,550

Pets Allowed
7417 Daniel Webster Dr Unit 3

7417 Daniel Webster Dr Unit 3, Winter Park, FL 32792
1 / 5
Studio, 1 Bath, 546 sq ft

$1,100

Pets Allowed Pool
3057 Aaron Burr Ave Unit 1

3057 Aaron Burr Ave Unit 1, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 1,066 sq ft

$1,700

Pets Allowed Pool Furnished
400 E Colonial Dr Unit 602

400 E Colonial Dr Unit 602, Orlando, FL 32803
1 / 5
2 Beds, 2 Baths, 1,189 sq ft

$2,000
104 S Interlachen Ave Unit 114

104 S Interlachen Ave Unit 114, Winter Park, FL 32789
1 / 5
2 Beds, 2 Baths, 1,143 sq ft

$4,650

Pets Allowed
572 Orange Dr Unit 65

572 Orange Dr Unit 65, Altamonte Springs, FL 32701
1 / 5
1 Bed, 1 Bath, 607 sq ft

$1,300

Cats Allowed
3716 Idlebrook Cir Unit 110

3716 Idlebrook Cir Unit 110, Casselberry, FL 32707
1 / 5
2 Beds, 2 Baths, 866 sq ft

$1,595
1160 Calle Del Norte Unit A

1160 Calle Del Norte Unit A, Casselberry, FL 32707
1 / 5
2 Beds, 2 Baths, 1,040 sq ft

$1,695
348 Georgetown Dr Unit 348

348 Georgetown Dr Unit 348, Casselberry, FL 32707
1 / 5
2 Beds, 2.5 Baths, 1,248 sq ft

$2,900

Furnished
8201 Sun Spring Cir Unit B1

8201 Sun Spring Cir Unit B1, Orlando, FL 32825
1 / 5
2 Beds, 2 Baths, 1,112 sq ft

$1,495
1731 Grayson Dr Unit 1

1731 Grayson Dr Unit 1, Orlando, FL 32825
1 / 5
2 Beds, 1 Bath, 2,787 sq ft

$2,700

Pets Allowed Furnished
3562 Aristotle Ave

3562 Aristotle Ave, Orlando, FL 32826
1 / 5
2 Beds, 2 Baths, 1,013 sq ft

$1,325

Pets Allowed
400 E Colonial Dr Unit 604

400 E Colonial Dr Unit 604, Orlando, FL 32803
1 / 5
2 Beds, 2 Baths, 1,189 sq ft

$2,100
1950 Summer Club Dr Unit 304

1950 Summer Club Dr Unit 304, Oviedo, FL 32765
1 / 5
2 Beds, 2 Baths, 975 sq ft

$1,500

Pets Allowed
8213 Claire Ann Dr Unit 203

8213 Claire Ann Dr Unit 203, Orlando, FL 32825
1 / 5
1 Bed, 1 Bath, 615 sq ft

$1,225

Pets Allowed
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

$1,450
1939 Summer Club Dr Unit 201

1939 Summer Club Dr Unit 201, Oviedo, FL 32765
1 / 5
3 Beds, 2 Baths, 1,180 sq ft

$2,000

Pets Allowed
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

Condos Florida Orange County Winter Park Oakcrest

Condos for Rent in Oakcrest, Winter Park, FL

A house seems like too much for you, but an apartment isn’t enough. Searching for condos in Oakcrest is the perfect compromise between a house and an apartment. Your new condo rental will give you just enough space to make your home in the city. With more than 1 million currently available rentals, you’ve come to the right place to find your next Winter Park condo at Apartments.com. Click on any one of these 3,227 available condos for rent in Winter Park to get information about neighborhoods, on-site amenities, services, nearby transit, and more. Let apartments.com help you find the perfect condo in Oakcrest. Once you’ve found your dream home, all there is left to do is pack up and move!

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