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Cheap Apartments for Rent in Winter Park, FL
1,920 Rentals
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1 Month FreeSTUDIO$1,330+1 BED$1,400+2 BEDS$1,750+ -
1 BED$1,344+2 BEDS$1,586+3 BEDS$2,399+Village Park Senior
550 W Denning Dr, Winter Park, FL 32789 -
Price Drop. $303 OffSTUDIO$1,348+1 BED$1,400+2 BEDS$1,414+3 BEDS$1,854+
Liv at Winter Park Apartment Homes
4755 N Goldenrod Rd, Winter Park, FL 32792 -
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1 BED, 1 BATH$1,3504818 Tangerine Ave Unit 4818
4818 Tangerine Ave, Winter Park, FL 32792 -
Price Drop. $250 Off|1 BED$1,355+2 BEDS$1,445+3 BEDS$1,775+
Cranes Landing Apartments
3440 N Goldenrod Rd, Winter Park, FL 32792 -
|1 BED$1,375+2 BEDS$1,599+3 BEDS$2,075+
Newport Colony Apartments in Casselberry
1166 Pointe Newport Ter, Casselberry, FL 32707 -
1 BED, 1 BATH$1,3802942 Antique Oaks Cir Unit 82
2942 Antique Oaks Cir, Winter Park, FL 32792 -
1 BED$1,393+2 BEDS$1,655+ARIUM Winter Park
3250 Bishop Park Dr, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,3953651 N Goldenrod Rd Unit C204
3651 N Goldenrod Rd, Winter Park, FL 32792 -
Good ValueTotal Monthly Price Total Monthly Price New1 BED$1,418+2 BEDS$1,553+3 BEDS$2,073+Base Rent$1,398 - $2,328Required Monthly Fees$20Utilities & EssentialsVariesTotal Monthly Price$1,418 - $2,348Atlas at Winter Park
3733 N Goldenrod Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,4001695 Lee Rd Unit C110
1695 Lee Rd, Winter Park, FL 32789 -
1 BED, 1 BATH$1,4003032 Antique Oaks Cir Unit 145
3032 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,400
1695 Lee Rd Unit D213
1695 Lee Rd, Winter Park, FL 32789 -
Good Value|1 BED$1,412+2 BEDS$2,736+3 BEDS$3,271+
Bainbridge Winter Park
1400 Morgan Stanley Ave, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,425Cozy 2/1 Duplex - College Park
121 E Evans St, Orlando, FL 32804 -
Price Drop. $237 Off1 BED$1,441+2 BEDS$1,748+3 BEDS$1,805+Stonecastle Apartment Homes
2015 New Stonecastle Ter, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,4503651 N Goldenrod Rd Unit 110
3651 N Goldenrod Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,4501555 Michigan Ave
1555 Michigan Ave, Winter Park, FL 32789 -
1 BED, 1 BATH$1,4502512 Musselwhite Ave Unit 3
2512 Musselwhite Ave, Orlando, FL 32804 -
2 BEDS, 2 BATHS$1,450Newly remodeled 2/2 condo Winter Park $300. incentive for move in by 6/15/2026 Unit A104
3651 Goldenrod Rd, Winter Park, FL 32792 -
1 Month Free1 BED$1,463+2 BEDS$1,768+Alvista Winter Park
3935 Sutton Place Blvd, Winter Park, FL 32792 -
Total Monthly Price Total Monthly Price New1 BED, 1 BATH$1,465Base Rent$1,465Required Monthly FeesNoneTotal Monthly Price$1,4652500 Lee Rd Unit 244
2500 Lee Rd, Winter Park, FL 32789 -
1 BED, 1 BATH$1,4751227 Minnesota St
1227 Minnesota St, Orlando, FL 32803 -
Exceptional ValueTotal Monthly Price Total Monthly Price NewSTUDIO$1,750+1 BED$1,562+2 BEDS$2,167+3 BEDS$2,909+Base Rent$1,487 - $3,255Required Monthly Fees$75Total Monthly Price$1,562 - $3,330
Aurora on the Trail
825 McCullough Ave, Orlando, FL 32803 -
1 BED$1,499+2 BEDS$1,799+
Calibre Bend Apartments
3924 Calibre Bend Ln, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,4991913 Truman Rd
1913 Truman Rd, Orlando, FL 32807 -
1 BED$1,499The Juliette
1225 Moselle Ave, Orlando, FL 32807 -
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2 BEDS, 1 BATH$1,5001695 Lee Rd Unit B114
1695 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,5001565 Michigan Ave
1565 Michigan Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,500
7340 Swallow Run Unit 7340
7340 Swallow Run, Winter Park, FL 32792 -
1 BED$1,515+2 BEDS$1,702+POSTE Winter Park
800 Semoran Park Dr, Winter Park, FL 32792 -
Total Monthly Price Total Monthly Price New1 BED, 1 BATH$1,522Base Rent$1,522Required Monthly FeesNoneTotal Monthly Price$1,5221500 Gay Rd Unit 1D
1500 Gay Rd, Winter Park, FL 32789 -
Exceptional Value1 BED$1,527+2 BEDS$2,081+3 BEDS$2,304+
Infinity off Baldwin Park
4000 Maguire Blvd, Orlando, FL 32803 -
3 BEDS, 1.5 BATHS$1,540105 Jergo Rd
105 Jergo Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,5501140 S Orlando Ave Unit E2
1140 S Orlando Ave, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,5752911 Antique Oaks Cir Unit 12
2911 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,575CONDOMINIUM FIRST FLOOR 2 BED 1 BATH, FULLY RENOVATED Unit #100
548 Cascade Cir, Casselberry, FL 32707 -
Rent SpecialSTUDIO$1,585+1 BED$1,695+2 BEDS$2,325+
Seven41 Winter Park
741 Clay St, Winter Park, FL 32789 -
|Total Monthly Price Total Monthly Price New1 BED$1,665+2 BEDS$1,953+3 BEDS$2,134+Base Rent$1,591 - $3,867Required Monthly Fees$74Total Monthly Price$1,665 - $3,431
Cortland Lake Howell
1280 Vinings Ln, Casselberry, FL 32707 -
Rent Special|Total Monthly Price Total Monthly Price New1 BED$1,628+2 BEDS$2,082+3 BEDS$2,998+Base Rent$1,593 - $5,419Required Monthly Fees$35Utilities & EssentialsVariesTotal Monthly Price$1,628 - $3,083
The Village at Lake Lily
925 S Orlando Ave, Maitland, FL 32751
Showing 42 of 234 results, Page 2 of 6
Winter Park at a Glance
Renting in Winter Park
Average Rental Rates and Apartment Sizes
- Apartment Type Average Sq Ft Average Rent
- Studio 535 Sq Ft $1,406 / mo
- 1 Bedroom 706 Sq Ft $1,462 / mo
- 2 Bedrooms 1,021 Sq Ft $1,758 / mo
- 3 Bedrooms 1,273 Sq Ft $2,031 / mo
- 4 Bedrooms 1,506 Sq Ft $1,940 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Lake Howell 747 Sq Ft $1,522/mo
- Fairview 757 Sq Ft $1,827/mo
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About Our Deals
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Price Drop
Apartment communities change their rental rates often - sometimes multiple times a day. We track the changes and keep you up to date when a rental rate decreases.
Best Value
"Best value" units are located in buildings rated three stars or higher. We label apartment rentals that are priced significantly less than similar high-quality units nearby.
Rent Specials
Apartment communities regularly advertise deals for new residents. Whether it's a move-in special or a free tv, we locate the rentals that offer a little something extra when you sign your lease.
Note: Based on community-supplied data and independent market research. Subject to change without notice.