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Apartments for Rent in Winter Park, FL with a Garage

359 Rentals
.
  3. Rent Special
    Rent Special
    |
    1 BED
    $1,540+
    2 BEDS
    $2,082+
    3 BEDS
    $3,122+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,505 - $5,379
    Required Monthly Fees$35
    Utilities & EssentialsVaries
    Total Monthly Price$1,540 - $3,157

    The Village at Lake Lily

    925 S Orlando Ave, Maitland, FL 32751
    (689) 219-5267
  4. |
    1 BED
    $1,655+
    2 BEDS
    $1,962+
    3 BEDS
    $2,103+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,581 - $4,061
    Required Monthly Fees$74
    Total Monthly Price$1,655 - $3,431

    Cortland Lake Howell

    1280 Vinings Ln, Casselberry, FL 32707
    (321) 710-4674
  5. Building Photo - Aurora on the Trail
    Exceptional Value
    STUDIO
    $1,750+
    1 BED
    $1,818+
    2 BEDS
    $2,167+
    3 BEDS
    $3,043+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,675 - $3,255
    Required Monthly Fees$75
    Total Monthly Price$1,750 - $3,330

    Aurora on the Trail

    825 McCullough Ave, Orlando, FL 32803
    (689) 219-5368
  7. 1 Month Free
    1 Month Free
    STUDIO
    $1,784+
    1 BED
    $2,107+
    2 BEDS
    $2,600+
    3 BEDS
    $3,714+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,696 - $9,144
    Required Monthly Fees$88
    Utilities & EssentialsVaries
    Total Monthly Price$1,784 - $3,714

    Vida at Health Village

    2680 N Orange Ave, Orlando, FL 32804
    (321) 621-2828
  8. Building Photo - Rosalia Winter Park 55+ Active Adult Community
    2 Months Free
    2 Months Free
    1 BED
    $1,917+
    2 BEDS
    $2,365+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,802 - $2,691
    Required Monthly Fees$115
    Utilities & EssentialsVaries
    Total Monthly Price$1,917 - $2,806

    Rosalia Winter Park 55+ Active Adult Community

    3045 Aloma Ave, Winter Park, FL 32792
    (321) 320-8654
  11. $499 Off
    Price Drop. $499 Off
    1 BED
    $1,677+
    2 BEDS
    $2,113+
    3 BEDS
    $2,425+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,647 - $2,903
    Required Monthly Fees$30
    Total Monthly Price$1,677 - $2,933

    Audubon Park

    990 Warehouse Rd, Orlando, FL 32803
    (689) 219-8885
  15. Building Photo - 2075 Jewell Ave
    5 BEDS, 4 BATHS
    $6,995
    Total Monthly Price Total Monthly Price New
    Base Rent$6,995
    Required Monthly FeesNone
    Total Monthly Price$6,995

    2075 Jewell Ave

    2075 Jewell Ave, Winter Park, FL 32789
  18. Building Photo - 2721 E Marks St
    3 BEDS, 2 BATHS
    $5,800
    Total Monthly Price Total Monthly Price New
    Base Rent$5,800
    Required Monthly FeesNone
    Total Monthly Price$5,800

    2721 E Marks St

    2721 E Marks St, Orlando, FL 32803
  20. Building Photo - 1886 Demetree Dr
    2 BEDS, 2 BATHS
    $3,350
    Total Monthly Price Total Monthly Price New
    Base Rent$3,350
    Required Monthly FeesNone
    Total Monthly Price$3,350

    1886 Demetree Dr

    1886 Demetree Dr, Winter Park, FL 32789
    Apply
  27. 3 BEDS, 3 BATHS
    $5,150

    870 Carver St

    870 Carver St, Winter Park, FL 32789
  38. 1 BED, 1 BATH
    $1,200

    301 Clark St

    301 Clark St, Eatonville, FL 32751

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Winter Park at a Glance

Average Rent

$1,460
(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 742 Sq Ft $1,512/mo
  • Fairview 753 Sq Ft $1,873/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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