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Apartments for Rent in Winter Park, FL with a Garage

546 Rentals
.
  5. $653 Off
    Price Drop. $653 Off
    1 BED
    $2,238+
    2 BEDS
    $3,144+
    3 BEDS
    $4,398+
    Total Monthly Price Total Monthly Price New
    Base Rent$2,181 - $4,341
    Required Monthly Fees$57
    Utilities & EssentialsVaries
    Total Monthly Price$2,238 - $4,398

    Baldwin Harbor

    1771-1887 Jake St, Orlando, FL 32814
    (689) 207-3563
  6. $250 Off
    Price Drop. $250 Off
    |
    1 BED
    $1,598+
    2 BEDS
    $2,382+
    3 BEDS
    $2,823+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,563 - $2,788
    Required Monthly Fees$35
    Utilities & EssentialsVaries
    Total Monthly Price$1,598 - $2,823

    The Village at Lake Lily

    925 S Orlando Ave, Maitland, FL 32751
    (689) 219-5267
  7. |
    1 BED
    $1,732+
    2 BEDS
    $2,143+
    3 BEDS
    $2,282+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,648 - $2,228
    Required Monthly Fees$84
    Utilities & EssentialsVaries
    Total Monthly Price$1,732 - $2,312

    Cortland Lake Howell

    1280 Vinings Ln, Casselberry, FL 32707
    (321) 710-4674
  13. $194 Off
    Price Drop. $194 Off
    STUDIO
    $1,831+
    1 BED
    $1,669+
    2 BEDS
    $2,277+
    3 BEDS
    $2,873+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,594 - $3,266
    Required Monthly Fees$75
    Total Monthly Price$1,669 - $3,341

    Aurora on the Trail

    825 McCullough Ave, Orlando, FL 32803
    (689) 219-5368
  14. Exceptional Value
    STUDIO
    $1,667+
    1 BED
    $1,987+
    2 BEDS
    $2,509+
    3 BEDS
    $3,330+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,579 - $3,242
    Required Monthly Fees$88
    Utilities & EssentialsVaries
    Total Monthly Price$1,667 - $3,330

    Vida at Health Village

    2680 N Orange Ave, Orlando, FL 32804
    (321) 621-2828
  16. Building Photo - Stonecastle Apartment Homes
    1 BED
    $1,592+
    2 BEDS
    $1,961+
    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
  19. $554 Off
    Price Drop. $554 Off
    1 BED
    $1,670+
    2 BEDS
    $2,103+
    3 BEDS
    $2,644+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,580 - $3,542
    Required Monthly Fees$90
    Total Monthly Price$1,670 - $3,632

    Audubon Park

    990 Warehouse Rd, Orlando, FL 32803
    (689) 219-8885
  25. 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
  30. 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
  32. Building Photo - 2037 Linden Rd
    STUDIO, 1 BATH
    $1,245+
    1 BED, 1 BATH
    $1,245+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,245
    Required Monthly FeesNone
    Total Monthly Price$1,245

    2037 Linden Rd Unit 2037lindenrdA

    2037 Linden Rd, Winter Park, FL 32792
    Apply
  33. Building Photo - 2810 Sandwell Dr
    3 BEDS, 2 BATHS
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000

    2810 Sandwell Dr

    2810 Sandwell Dr, Winter Park, FL 32792
  34. 3 BEDS, 3.5 BATHS
    $4,100
    Total Monthly Price Total Monthly Price New
    Base Rent$4,100
    Required Monthly FeesNone
    Total Monthly Price$4,100

    1733 Prospect Ave

    1733 Prospect Ave, Orlando, FL 32814
  39. 4 BEDS, 2.5 BATHS
    $3,100

    2251 Nairn Dr

    2251 Nairn Dr, Winter Park, FL 32792
Showing 42 of 57 results, Page 1 of 2

Winter Park at a Glance

Average Rent

$1,479
(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)

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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