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Cheap Apartments for Rent in Winter Park, FL
1,995 Rentals
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2 BEDS, 1 BATH$1,7251111 Hardy Ave
1111 Hardy Ave, Orlando, FL 32803 -
Price Drop. $306 Off|STUDIO$1,813+1 BED$1,730+2 BEDS$2,130+3 BEDS$2,787+The Ivy Residences at Health Village Apart...
2650 Dade Ave, Orlando, FL 32804 -
3 BEDS, 2 BATHS$1,7453801 Grant Blvd
3801 Grant Blvd, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,7492414 Formosa Ave
2414 Formosa Ave, Orlando, FL 32804 -
Price Drop. $435 Off|STUDIO$1,750+1 BED$1,800+2 BEDS$2,150+The Majestic at Downtown Baldwin Park
4828 New Broad St, Orlando, FL 32814 -
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2 BEDS, 2 BATHS$1,7503019 Casselwood St
3019 Casselwood St, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,7503057 Aaron Burr Ave Unit 1
3057 Aaron Burr Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,750Charming 2-Bedroom Condo in Scenic Winter ... Unit 204
1250 S Denning Dr, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$1,750435 Eaton St Unit B
435 Eaton St, Eatonville, FL 32751 -
3 BEDS, 2 BATHS$1,750
6805 Bonavista Ct
6805 Bonavista Ct, Winter Park, FL 32792 -
Rent Special|STUDIO$1,753+1 BED$1,875+2 BEDS$2,140+3 BEDS$3,122+Juno Winter Park
1305 Morgan Stanley Ave, Winter Park, FL 32789 -
Price Drop. $950 Off1 BED$1,756+2 BEDS$2,150+3 BEDS$3,878+Baldwin Harbor
1771-1887 Jake St, Orlando, FL 32814 -
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STUDIO$1,795+1 BED$1,837+2 BEDS$2,333+Vida at Health Village
2680 N Orange Ave, Orlando, FL 32804 -
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2 BEDS, 2 BATHS$1,7951500 Gay Rd Unit 18C
1500 Gay Rd, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$1,7953136 Patel Dr
3136 Patel Dr, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,799
Well maintained 2 bedroom property with lo...
7781 Fernbrook Way, Winter Park, FL 32792 -
2 BEDS$1,799
The Fisher Apartments | Modern 1 & 2 Bedro...
2001 Glenridge Way, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$1,8001150 Carmel Cir Unit 308
1150 Carmel Cir, Casselberry, FL 32707 -
2 BEDS, 2 BATHS$1,800668 Montego Bay Ct Unit 668
668 Montego Bay Ct, Winter Park, FL 32792 -
3 BEDS, 1 BATH$1,800Northeast Orlando Home
1212 Sasoon Ave, Orlando, FL 32803 -
2 BEDS, 2 BATHS$1,800668 Montego Bay Ct
668 Montego Bay Ct, Winter Park, FL 32792 -
1 BED$1,802+2 BEDS$2,200+Rosalia Winter Park 55+ Active Adult Commu...
3045 Aloma Ave, Winter Park, FL 32792 -
STUDIO$1,804+1 BED$1,989+2 BEDS$2,284+3 BEDS$3,064+Enders Place at Baldwin Park
4220 New Broad St, Orlando, FL 32814 -
Rent Special|1 BED$1,830+2 BEDS$2,255+3 BEDS$3,150+MAA Baldwin Park
4688 New Broad St, Orlando, FL 32814 -
Price Drop. $319 Off|1 BED$1,837+2 BEDS$2,211+3 BEDS$3,260+Azul Baldwin Park
4460 Lower Park Rd, Orlando, FL 32814 -
2 BEDS, 1 BATH$1,8402510 Roxbury Rd
2510 Roxbury Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,840Fully Furnished 2/2 Condo!
7429 Daniel Webster Dr, Winter Park, FL 32792 -
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3 BEDS, 2 BATHS$1,8813392 Bougainvillea Dr
3392 Bougainvillea Dr, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$1,8852111 Conifer Ave
2111 Conifer Ave, Winter Park, FL 32792 -
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3 BEDS, 2 BATHS$1,895Cute 3/2 Townhome in Winter Park - close t...
758 Warrenton Rd, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$1,895Townhome in Winter Park
200 Sandlewood Trail, Winter Park, FL 32789 -
Price Drop. $508 Off|1 BED$1,898+2 BEDS$2,376+3 BEDS$3,266+Perla Gem Lake
100 Boucle Jeanne Cir, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,900151 Stefanik Rd
151 Stefanik Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,900151 Stefanik Rd
151 Stefanik Rd, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,900
2822 Plaza Terrace Dr Unit 2822
2822 Plaza Terrace Dr, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,9001835 Biscayne Dr
1835 Biscayne Dr, Winter Park, FL 32789
Showing 42 of 306 results, Page 4 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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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.