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Two Bedroom Apartments for Rent in Winter Park, FL

806 Rentals
.
  1. Building Photo - Gables Baldwin Park
    Rent Special
    Rent Special
    |
    2 BEDS
    $2,996
    Total Monthly Price Total Monthly Price New
    Base Rent$2,948 - $6,246
    Required Monthly Fees$48
    Utilities & EssentialsVaries
    Total Monthly Price$2,996 - $4,276

    Gables Baldwin Park

    2050 Jake St, Orlando, FL 32814
    (470) 305-6691
  4. |
    2 BEDS
    $2,147
    Total Monthly Price Total Monthly Price New
    Base Rent$2,014 - $3,910
    Required Monthly Fees$133
    Utilities & EssentialsVaries
    Total Monthly Price$2,147 - $2,742

    Vintage Winter Park Apartments

    7490 Dwell Well Way, Winter Park, FL 32792
    (689) 220-1305
  13. 2 BEDS
    $2,911
    Total Monthly Price Total Monthly Price New
    Base Rent$2,854 - $3,469
    Required Monthly Fees$57
    Utilities & EssentialsVaries
    Total Monthly Price$2,911 - $3,526

    Baldwin Harbor

    1771-1887 Jake St, Orlando, FL 32814
    (689) 207-3563
  14. Rent Special
    Rent Special
    |
    2 BEDS
    $2,086
    Total Monthly Price Total Monthly Price New
    Base Rent$2,051 - $4,663
    Required Monthly Fees$35
    Utilities & EssentialsVaries
    Total Monthly Price$2,086 - $2,858

    The Village at Lake Lily

    925 S Orlando Ave, Maitland, FL 32751
    (689) 219-5267
  15. |
    2 BEDS
    $1,970
    Total Monthly Price Total Monthly Price New
    Base Rent$1,886 - $3,330
    Required Monthly Fees$84
    Utilities & EssentialsVaries
    Total Monthly Price$1,970 - $2,210

    Cortland Lake Howell

    1280 Vinings Ln, Casselberry, FL 32707
    (321) 710-4674
  32. Good Value
    2 BEDS
    $2,373
    Total Monthly Price Total Monthly Price New
    Base Rent$2,298 - $2,781
    Required Monthly Fees$75
    Total Monthly Price$2,373 - $2,856

    Aurora on the Trail

    825 McCullough Ave, Orlando, FL 32803
    (689) 219-5368
  35. 1 Month Free
    1 Month Free
    2 BEDS
    $2,374
    Total Monthly Price Total Monthly Price New
    Base Rent$2,286 - $5,057
    Required Monthly Fees$88
    Utilities & EssentialsVaries
    Total Monthly Price$2,374 - $2,534

    Vida at Health Village

    2680 N Orange Ave, Orlando, FL 32804
    (321) 621-2828
Showing 42 of 132 results, Page 1 of 4

Winter Park at a Glance

Average Rent

$1,486
(All bedrooms and property types)
Learn more about
Average Rent in Winter Park
7

School Rating

out of 10 Rating
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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 737 Sq Ft $1,581/mo
  • Fairview 731 Sq Ft $1,868/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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Winter Park Apartments for Rent in Your Budget

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