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Apartments for Rent in Winter Park, FL with a Garage

484 Rentals
.
  4. $265 Off
    Price Drop. $265 Off
    STUDIO
    $1,798+
    1 BED
    $2,274+
    2 BEDS
    $2,749+
    3 BEDS
    $3,373+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,699 - $3,475
    Required Monthly Fees$99
    Utilities & EssentialsVaries
    Total Monthly Price$1,798 - $3,574

    Enders Place at Baldwin Park

    4220 New Broad St, Orlando, FL 32814
    (689) 220-2141
  5. $566 Off
    Price Drop. $566 Off
    1 BED
    $1,962+
    2 BEDS
    $3,052+
    3 BEDS
    $3,915+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,885 - $5,057
    Required Monthly Fees$77
    Utilities & EssentialsVaries
    Total Monthly Price$1,962 - $5,134

    Baldwin Harbor

    1771-1887 Jake St, Orlando, FL 32814
    (689) 207-3563
  6. Rent Special
    Rent Special
    |
    1 BED
    $1,694+
    2 BEDS
    $2,373+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,659 - $4,317
    Required Monthly Fees$35
    Utilities & EssentialsVaries
    Total Monthly Price$1,694 - $4,352

    The Village at Lake Lily

    925 S Orlando Ave, Maitland, FL 32751
    (689) 219-5267
  7. $165 Off
    Price Drop. $165 Off
    |
    1 BED
    $1,545+
    2 BEDS
    $1,863+
    3 BEDS
    $2,098+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,461 - $2,214
    Required Monthly Fees$84
    Utilities & EssentialsVaries
    Total Monthly Price$1,545 - $2,298

    Cortland Lake Howell

    1280 Vinings Ln, Casselberry, FL 32707
    (321) 710-4674
  15. Good Value
    STUDIO
    $1,831+
    1 BED
    $1,719+
    2 BEDS
    $2,171+
    3 BEDS
    $2,691+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,644 - $3,178
    Required Monthly Fees$75
    Total Monthly Price$1,719 - $3,253

    Aurora on the Trail

    825 McCullough Ave, Orlando, FL 32803
    (689) 219-5368
  16. 1 Month Free
    1 Month Free
    STUDIO
    $1,827+
    1 BED
    $2,044+
    2 BEDS
    $2,715+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,739 - $2,772
    Required Monthly Fees$88
    Utilities & EssentialsVaries
    Total Monthly Price$1,827 - $2,860

    Vida at Health Village

    2680 N Orange Ave, Orlando, FL 32804
    (321) 621-2828
  17. Building Photo - Stonecastle Apartment Homes
    1 BED
    $1,592+
    2 BEDS
    $1,932+
    3 BEDS
    $1,956+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,441 - $2,620
    Required Monthly Fees$151
    Utilities & EssentialsVaries
    Total Monthly Price$1,592 - $2,771

    Stonecastle Apartment Homes

    2015 New Stonecastle Ter, Winter Park, FL 32792
    (689) 219-5272
  20. Rent Special
    Rent Special
    STUDIO
    $1,600+
    1 BED
    $1,700+
    2 BEDS
    $1,475+
    3 BEDS
    $1,750+

    Hannibal Square

    433 W New England Ave, Winter Park, FL 32789
    (689) 207-3890
  22. $418 Off
    Price Drop. $418 Off
    1 BED
    $1,771+
    2 BEDS
    $1,864+
    3 BEDS
    $2,538+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,681 - $3,024
    Required Monthly Fees$90
    Total Monthly Price$1,771 - $3,114

    Audubon Park

    990 Warehouse Rd, Orlando, FL 32803
    (689) 219-8885
  23. 3 BEDS, 2 BATHS
    $4,354
    Total Monthly Price Total Monthly Price New
    Base Rent$4,354
    Required Monthly FeesNone
    Total Monthly Price$4,354

    1915 Taylor Ave

    1915 Taylor Ave, Winter Park, FL 32792
    Apply
  31. Building Photo - 155 Stefanik Rd
    2 BEDS, 2 BATHS
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000

    155 Stefanik Rd

    155 Stefanik Rd, Winter Park, FL 32792
  32. Building Photo - 1627 Orange Ave
    3 BEDS, 2 BATHS
    $2,750
    Total Monthly Price Total Monthly Price New
    Base Rent$2,750
    Required Monthly FeesNone
    Total Monthly Price$2,750

    1627 Orange Ave

    1627 Orange Ave, Winter Park, FL 32789
  33. 3 BEDS, 2 BATHS
    $2,300
    Total Monthly Price Total Monthly Price New
    Base Rent$2,300
    Required Monthly FeesNone
    Total Monthly Price$2,300

    524 N Lakemont Ave

    524 N Lakemont Ave, Winter Park, FL 32792
  34. 2 BEDS, 3 BATHS
    $2,100
    Total Monthly Price Total Monthly Price New
    Base Rent$2,100
    Required Monthly FeesNone
    Total Monthly Price$2,100

    2605 Galliano Cir

    2605 Galliano Cir, Winter Park, FL 32792
  35. 5 BEDS, 3 BATHS
    $6,700
    Total Monthly Price Total Monthly Price New
    Base Rent$6,700
    Required Monthly FeesNone
    Total Monthly Price$6,700

    3782 Kinsley Pl

    3782 Kinsley Pl, Winter Park, FL 32792
  40. Building Photo - 3217 Royal St
    3 BEDS, 2 BATHS
    $2,200
    Total Monthly Price Total Monthly Price New
    Base Rent$2,200
    Required Monthly FeesNone
    Total Monthly Price$2,200

    3217 Royal St

    3217 Royal St, Winter Park, FL 32792
    Apply
  41. Building Photo - 1509 Springtime Loop
    3 BEDS, 2 BATHS
    $2,695
    Total Monthly Price Total Monthly Price New
    Base Rent$2,695
    Required Monthly FeesNone
    Total Monthly Price$2,695

    1509 Springtime Loop

    1509 Springtime Loop, Winter Park, FL 32792
    Apply
  42. Building Photo - 4062 Markham Pl
    3 BEDS, 2.5 BATHS
    $4,450
    Total Monthly Price Total Monthly Price New
    Base Rent$4,450
    Required Monthly FeesNone
    Total Monthly Price$4,450

    4062 Markham Pl

    4062 Markham Pl, Orlando, FL 32814
    Apply
Showing 42 of 74 results, Page 1 of 2

Winter Park at a Glance

Average Rent

$1,474
(All bedrooms and property types)
Learn more about
Average Rent in Winter Park
7

School Rating

out of 10 Rating
Learn more about
Schools in Winter Park

Winter Park, FL Apartments for Rent

Winter Park was founded as a resort community by northern business magnates in the late 19th century and has maintained its reputation as one of Central Florida's most desirable places to live. Those searching for apartments for rent in Winter Park will discover tree-lined brick streets, a chain of interconnected lakes, and the cultural centerpiece of Park Avenue, which features boutique shops, art galleries, and dining options. The city is also home to Rollins College and the Charles Hosmer Morse Museum of American Art, which houses the world's most comprehensive collection of Tiffany glass.

Renting in Winter Park provides convenient access to both local attractions and the broader Orlando metropolitan area. The city's apartment communities range from lakefront properties to garden-style residences near downtown, with options spanning studios to multi-bedroom layouts. Major highways including Interstate 4 are easily accessible for commuters heading to Orlando's business districts, theme parks, and employment centers. The 47.6-acre Mead Botanical Garden and the city's scenic canal system offer outdoor recreation, while Park Avenue's walkable downtown creates opportunities for shopping and entertainment without leaving the city limits.

Renting in Winter Park

Average Rental Rates and Apartment Sizes

Top Budget-Friendly Neighborhoods in Winter Park

(For 1 bedroom apartments)
  • Neighborhoods Average Sq Ft Average Rent
  • Lake Howell 727 Sq Ft $1,536/mo
  • Fairview 741 Sq Ft $1,796/mo

Education

GreatSchools Rating
Winter Park High

Public High School

Public
Grades 9-12
3,369 Students
GreatSchools Rating
Winter Park High School

Public High School

Public
Grades 9-12
3,304 Students
GreatSchools Rating
Lake Howell High School

Public High School

Public
Grades 9-12
2,239 Students

Data provided by GreatSchools.org 2025 © 2025. All rights reserved.

Apartments for Rent Near Winter Park

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