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Cheap Apartments for Rent in Winter Park, FL
2,015 Rentals
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1 BED$1,299+2 BEDS$1,436+3 BEDS$1,929+Summerlin at Winter Park Apartments
3207 Rosebud Ln, Winter Park, FL 32792 -
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2 BEDS, 1 BATH$1,300907 Dowd Ave Unit 3 (Upstairs 2/1)
907 Dowd Ave, Orlando, FL 32804 -
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2 BEDS$1,599+3 BEDS$1,849+Azure Winter Park
3650 Summer Wind Dr, Winter Park, FL 32792 -
1 BED, 1 BATH$1,350Beautiful 1/1 Remodeled Condo for Rent in ... Unit 52
2929 Antique Oaks Cir, Winter Park, FL 32792 -
1 BED$1,351+2 BEDS$1,796+3 BEDS$2,311+The Taylor at Winter Park
2000 Village Ln, Winter Park, FL 32792 -
Good Value|1 BED$1,375+2 BEDS$1,735+3 BEDS$2,075+Newport Colony Apartments in Casselberry
1166 Pointe Newport Ter, Casselberry, FL 32707 -
1 BED, 1 BATH$1,375Beutiful 1/1 Condo x Rent in Winter Park ... Unit 612
200 St Andrews Blvd, Winter Park, FL 32792 -
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2 BEDS, 1 BATH$1,395113 E Smith St Unit 6
113 E Smith St, Orlando, FL 32804 -
1 BED$1,399+2 BEDS$1,780+3 BEDS$1,928+Stonecastle Apartment Homes
2015 New Stonecastle Ter, Winter Park, FL 32792 -
1 BED, 1 BATH$1,3991000 S Semoran Blvd Unit 703
1000 S Semoran Blvd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,4003057 Aaron Burr Ave Unit 2
3057 Aaron Burr Ave, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,400825 N Primrose Dr Unit 106
825 N Primrose Dr, Orlando, FL 32803 -
2 BEDS, 2 BATHS$1,4003651 N Goldenrod Rd Unit B109
3651 N Goldenrod Rd, Winter Park, FL 32792 -
1 BED$1,410+2 BEDS$1,625+Whisper Lake Apartments
3250 Whisper Lake Ln, Winter Park, FL 32792 -
1 BED$1,418+2 BEDS$1,646+3 BEDS$1,740+Atlas at Winter Park
3733 N Goldenrod Rd, Winter Park, FL 32792 -
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Price Drop. $482 Off|1 BED$1,441+2 BEDS$1,925+3 BEDS$3,021+The Village at Lake Lily
925 S Orlando Ave, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,4501166 Paseo De Las Flores Unit C
1166 Paseo De Las Flores, Casselberry, FL 32707 -
2 BEDS, 2 BATHS$1,4507229 Swallow Run
7229 Swallow Run, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,4502 Bed/2 Bath, 2nd Floor Condo at Marbeya C...
1166 Paseo De Las Flores, Casselberry, FL 32707 -
Rent Special|1 BED$1,475+2 BEDS$1,600+3 BEDS$2,025+Oak Reserve at Winter Park
541 Oak Reserve Ln, Winter Park, FL 32792 -
3 BEDS, 1.5 BATHS$1,4751112 Princewood Dr
1112 Princewood Dr, Orlando, FL 32810 -
2 BEDS, 1 BATH$1,4951919 Canton St
1919 Canton St, Orlando, FL 32803 -
1 BED$1,497+2 BEDS$1,701+Calibre Bend Apartments
3924 Calibre Bend Ln, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,4991500 Michigan Ave
1500 Michigan Ave, Winter Park, FL 32789 -
1 BED$1,499The Juliette | 1 Bedroom Apartments in Orl...
1225 Moselle Ave, Orlando, FL 32807 -
STUDIO$1,600+1 BED$1,550+2 BEDS$1,500+Hannibal Square
433 W New England Ave, Winter Park, FL 32789 -
1 BED, 1 BATH$1,5002500 Lee Rd Unit 244
2500 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,500496 Banyon Tree Cir Unit 204
496 Banyon Tree Cir, Maitland, FL 32751 -
1 BED, 1 BATH$1,500
2500 Lee Rd Unit 244
2500 Lee Rd, Winter Park, FL 32789 -
1 BED, 1 BATH$1,500540 Cascade Cir Unit 104
540 Cascade Cir, Casselberry, FL 32707 -
2 BEDS, 2 BATHS$1,500** ONE MONTH FREE!!!!** NEWLY RENOVATED 2 ...
1165 Paseo De Las Flores Apt C, Casselberry, FL 32707 -
2 BEDS, 1 BATH$1,5002nd story, 2/1, updated unit on the Winter...
2406 Branch Way, Maitland, FL 32751 -
Price Drop. $287 OffSTUDIO$1,505+1 BED$1,652+2 BEDS$1,954+3 BEDS$3,110+Berkshire Winter Park
1874 Harmon Ave, Winter Park, FL 32789 -
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Rent Special|1 BED$1,517+2 BEDS$1,780+3 BEDS$1,985+Cortland Lake Howell
1280 Vinings Ln, Casselberry, FL 32707 -
1 BED, 1 BATH$1,5253060 George Mason Ave Unit 10C
3060 George Mason Ave, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$1,5253007 George Mason Ave Unit H
3007 George Mason Ave, Winter Park, FL 32792
Showing 42 of 310 results, Page 2 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 $1,365 / mo
- 1 Bedroom 709 Sq Ft $1,459 / mo
- 2 Bedrooms 1,020 Sq Ft $1,696 / mo
- 3 Bedrooms 1,273 Sq Ft $2,015 / 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
- Winter Park Woods 760 Sq Ft $1,415/mo
- Winter Park Pines 668 Sq Ft $1,420/mo
- Eastbrook 737 Sq Ft $1,438/mo
- Four Seasons 622 Sq Ft $1,450/mo
- Winter Park Pines Merrie Oaks 622 Sq Ft $1,450/mo
- Laurel Springs 742 Sq Ft $1,473/mo
- Albert Lee Ridge 743 Sq Ft $1,493/mo
- Cedarwood Village 657 Sq Ft $1,537/mo
- Villas of Casselberry 775 Sq Ft $1,561/mo
- Georgetown Estates 735 Sq Ft $1,573/mo
Getting Around Winter Park
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Best Value
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Note: Based on community-supplied data and independent market research. Subject to change without notice.