
Deals & Discount Filters
Apartments for Rent in Winter Park, FL
1,979 Rentals
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4 BEDS, 3 BATHS$2,495
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4 BEDS, 2 BATHS$2,375
2336 High St
2336 High St, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$2,750
690 Osceola Ave Unit 502
690 Osceola Ave, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,695
851 Miles Ave Unit 21
851 Miles Ave, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,650
226 Harvard St
226 Harvard St, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,650
5314 Andrus Ave
5314 Andrus Ave, Orlando, FL 32810 -
2 BEDS, 1 BATH$2,150
1004 Fleck Ave
1004 Fleck Ave, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,350
113 E Smith St Unit 6
113 E Smith St, Orlando, FL 32804 -
1 BED, 1 BATH$1,150
2525 Caper Ln Unit 205
2525 Caper Ln, Maitland, FL 32751 -
2 BEDS, 1 BATH$2,195
2203 Oregon St
2203 Oregon St, Orlando, FL 32803 -
1 BED, 1 BATH$1,500
540 Cascade Cir Unit 104
540 Cascade Cir, Casselberry, FL 32707 -
3 BEDS, 2 BATHS$2,250
410 Poplar Ct
410 Poplar Ct, Maitland, FL 32751 -
1 BED, 1 BATH$1,700
1483 Lake Baldwin Ln Unit C
1483 Lake Baldwin Ln, Orlando, FL 32814 -
2 BEDS, 1 BATH$2,950
1504 Minnesota St
1504 Minnesota St, Orlando, FL 32803 -
2 BEDS, 2 BATHS$2,500
808 Malone Dr
808 Malone Dr, Orlando, FL 32810 -
5 BEDS, 8 BATHS$22,500
3260 Lake Shore Dr
3260 Lake Shore Dr, Orlando, FL 32803 -
1 BED, 1 BATH$2,250
1911 Canton St
1911 Canton St, Orlando, FL 32803 -
1 BED, 1 BATH$2,300
40 E Princeton St
40 E Princeton St, Orlando, FL 32804 -
1 BED, 1 BATH$1,000
421 E Kennedy Blvd
421 E Kennedy Blvd, Eatonville, FL 32751 -
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 -
3 BEDS, 2 BATHS$1,800
1150 Carmel Cir Unit 308
1150 Carmel Cir, Casselberry, FL 32707 -
3 BEDS, 2.5 BATHS$2,290
824 Town Cir
824 Town Cir, Maitland, FL 32751 -
3 BEDS, 3.5 BATHS$3,700
4701 Anson Ln
4701 Anson Ln, Orlando, FL 32814 -
2 BEDS, 2 BATHS$1,500
496 Banyon Tree Cir Unit 204
496 Banyon Tree Cir, Maitland, FL 32751 -
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$1,495
1919 Canton St
1919 Canton St, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,925
2512 Musselwhite Ave Unit #1
2512 Musselwhite Ave, Orlando, FL 32804 -
3 BEDS, 2.5 BATHS$3,590
1507 Lake Baldwin Ln
1507 Lake Baldwin Ln, Orlando, FL 32814 -
2 BEDS, 1.5 BATHS$1,850
2822 Plaza Terrace Dr Unit 2822
2822 Plaza Terrace Dr, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,600
825 N Primrose Dr Unit 113
825 N Primrose Dr, Orlando, FL 32803 -
1 BED, 1 BATH$1,650
4499 Twinview Ln
4499 Twinview Ln, Orlando, FL 32814 -
3 BEDS, 2.5 BATHS$4,300
1550 Lake Baldwin Ln
1550 Lake Baldwin Ln, Orlando, FL 32814 -
2 BEDS, 1 BATH$2,550
2621 Illinois St
2621 Illinois St, Orlando, FL 32803 -
3 BEDS, 3.5 BATHS$3,795
1865 Britlyn Alley
1865 Britlyn Alley, Orlando, FL 32814 -
2 BEDS, 2 BATHS$1,550
550 Flemming Way Unit 200
550 Flemming Way, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,290
64 Taylor Ave
64 Taylor Ave, Eatonville, FL 32751 -
1 BED, 1 BATH$1,375
2521 Caper Ln Unit 203
2521 Caper Ln, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,650
Winter Park 2/2 Condo in Charming Parkview... Unit 79
2941 Antique Oaks Cir, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$1,995
7473 Belle River Ct
7473 Belle River Ct, Winter Park, FL 32792 -
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
Showing 42 of 321 results, Page 5 of 8
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
Average Rent in Nearby Cities
(For 1 bedroom apartments)- Cities Average Rent
- Winter Park $1,598/mo
- Maitland $1,768/mo
- Fern Park $1,295/mo
- Eatonville $992/mo
- Casselberry $1,611/mo
- Longwood $1,762/mo
- Altamonte Springs $1,614/mo
- Lockhart $1,333/mo
- Orlando $1,664/mo
- Belle Isle $1,275/mo
- Pine Castle $1,183/mo
Getting Around Winter Park
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