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Two Bedroom Apartments for Rent in Winter Park, FL
847 Rentals
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2 BEDS, 1 BATH$1,695
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2 BEDS, 2 BATHS$1,600
1250 S Denning Dr Unit 232
1250 S Denning Dr, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,750
3057 Aaron Burr Ave Unit 1
3057 Aaron Burr Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,550
1000 S Semoran Blvd Unit 115
1000 S Semoran Blvd, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,495
1919 Canton St
1919 Canton St, Orlando, FL 32803 -
2 BEDS, 2 BATHS$2,500
808 Malone Dr
808 Malone Dr, Orlando, FL 32810 -
2 BEDS, 1 BATH$2,950
1504 Minnesota St
1504 Minnesota St, Orlando, FL 32803 -
2 BEDS, 1.5 BATHS$1,850
2822 Plaza Terrace Dr Unit 2822
2822 Plaza Terrace Dr, Orlando, FL 32803 -
2 BEDS, 2 BATHS$1,500
496 Banyon Tree Cir Unit 204
496 Banyon Tree Cir, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,350
113 E Smith St Unit 6
113 E Smith St, Orlando, FL 32804 -
2 BEDS, 2 BATHS$1,450
1166 Paseo De Las Flores Unit C
1166 Paseo De Las Flores, Casselberry, FL 32707 -
2 BEDS, 1 BATH$1,925
2512 Musselwhite Ave Unit #1
2512 Musselwhite Ave, Orlando, FL 32804 -
2 BEDS, 1 BATH$2,150
1004 Fleck Ave
1004 Fleck Ave, Orlando, FL 32804 -
2 BEDS, 1 BATH$2,550
2621 Illinois St
2621 Illinois St, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,700
5314 Andrus Ave
5314 Andrus Ave, Orlando, FL 32810 -
2 BEDS, 1 BATH$2,195
2203 Oregon St
2203 Oregon St, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,600
825 N Primrose Dr Unit 113
825 N Primrose Dr, Orlando, FL 32803 -
2 BEDS, 1 BATH$2,000
12 W Hazel St
12 W Hazel St, Orlando, FL 32804 -
2 BEDS, 2.5 BATHS$2,000
33 E Princeton St
33 E Princeton St, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,290
64 Taylor Ave
64 Taylor Ave, Eatonville, FL 32751 -
2 BEDS, 2 BATHS$1,550
550 Flemming Way Unit 200
550 Flemming Way, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,595
115 Scottsdale Square
115 Scottsdale Square, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$1,525
3007 George Mason Ave Unit H
3007 George Mason Ave, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$2,380
645 Huntington Ave
645 Huntington Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,695
200 St Andrews Blvd Unit 3502
200 St Andrews Blvd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,600
3651 N Goldenrod Rd
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,800
668 Montego Bay Ct
668 Montego Bay Ct, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,900
250 Carolina Ave Unit 250
250 Carolina Ave, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,100
1701 Winter Green Blvd
1701 Winter Green Blvd, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,900
1835 Biscayne Dr
1835 Biscayne Dr, Winter Park, FL 32789 -
2 BEDS, 1 BATH$2,150
1919 Azalea Ave
1919 Azalea Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,795
1500 Gay Rd Unit 18C
1500 Gay Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,520
"Charming 2-Bed, 2-Bath Retreat in Winter ...
2611 Holly Rd, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,499
1500 Michigan Ave
1500 Michigan Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,400
3651 N Goldenrod Rd Unit B109
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$2,200
AVAILALBE OCTOBER! Two story Townhouse loc...
848 Miles Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,700
Excellent location Unit 4968
4968 Tangerine Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,840
Fully Furnished 2/2 Condo!
7429 Daniel Webster Dr, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,725
2Bed/1.5Bath TOWNHOUSE IN WINTER PARK!! ...
4954 Tangerine Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,750
Charming 2-Bedroom Condo in Scenic Winter ... Unit 204
1250 S Denning Dr, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,675
Winter Park 2/2 Condo in Charming Parkview... Unit 79
2941 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$2,725
FIRST MONTH FREE - Beautiful remodeled 2 ...
939 Aragon Ave, Winter Park, FL 32789
Showing 42 of 162 results, Page 3 of 4
Winter Park at a Glance
Renting in Winter Park
Average Rental Rates and Apartment Sizes
- Apartment Type Average Sq Ft Average Rent
- Studio 539 Sq Ft $1,400 / mo
- 1 Bedroom 709 Sq Ft $1,467 / mo
- 2 Bedrooms 1,020 Sq Ft $1,701 / mo
- 3 Bedrooms 1,273 Sq Ft $2,030 / mo
- 4 Bedrooms 1,506 Sq Ft $1,535 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Whisperwood 741 Sq Ft $1,395/mo
- Four Seasons 622 Sq Ft $1,412/mo
- Winter Park Pines Merrie Oaks 622 Sq Ft $1,412/mo
- Winter Park Pines 739 Sq Ft $1,414/mo
- Winter Park Woods 761 Sq Ft $1,416/mo
- Eastbrook 737 Sq Ft $1,464/mo
- Laurel Springs 746 Sq Ft $1,482/mo
- Albert Lee Ridge 743 Sq Ft $1,493/mo
- Cedarwood Village 652 Sq Ft $1,526/mo
- Glenmoor 708 Sq Ft $1,552/mo
Getting Around Winter Park
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