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Luxury Apartments for Rent in Winter Park, FL

334 Rentals
.
  1. Building Photo - Gables Baldwin Park
    Rent Special
    Rent Special
    |
    STUDIO
    $2,238+
    1 BED
    $2,458+
    2 BEDS
    $3,108+
    3 BEDS
    $4,367+
    Total Monthly Price Total Monthly Price New
    Base Rent$2,190 - $4,319
    Required Monthly Fees$48
    Utilities & EssentialsVaries
    Total Monthly Price$2,238 - $4,367

    Gables Baldwin Park

    2050 Jake St, Orlando, FL 32814
    (470) 305-6691
  6. $250 Off
    Price Drop. $250 Off
    |
    1 BED
    $1,714+
    2 BEDS
    $2,079+
    3 BEDS
    $2,852+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,679 - $2,817
    Required Monthly Fees$35
    Utilities & EssentialsVaries
    Total Monthly Price$1,714 - $2,852

    The Village at Lake Lily

    925 S Orlando Ave, Maitland, FL 32751
    (689) 219-5267
  7. |
    1 BED
    $1,688+
    2 BEDS
    $2,075+
    3 BEDS
    $2,259+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,604 - $2,205
    Required Monthly Fees$84
    Utilities & EssentialsVaries
    Total Monthly Price$1,688 - $2,289

    Cortland Lake Howell

    1280 Vinings Ln, Casselberry, FL 32707
    (321) 710-4674
  8. 1 Month Free
    1 Month Free
    STUDIO
    $1,903
    Total Monthly Price Total Monthly Price New
    Base Rent$1,804 - $2,300
    Required Monthly Fees$99
    Utilities & EssentialsVaries
    Total Monthly Price$1,903 - $2,399

    Enders Place at Baldwin Park

    4220 New Broad St, Orlando, FL 32814
    (689) 220-2141
  9. 1 BED
    $2,342+
    2 BEDS
    $2,876+
    3 BEDS
    $4,948+
    Total Monthly Price Total Monthly Price New
    Base Rent$2,265 - $4,871
    Required Monthly Fees$77
    Utilities & EssentialsVaries
    Total Monthly Price$2,342 - $4,948

    Baldwin Harbor

    1771-1887 Jake St, Orlando, FL 32814
    (689) 207-3563
  10. $267 Off
    Price Drop. $267 Off
    |
    1 BED
    $1,684+
    2 BEDS
    $2,199+
    3 BEDS
    $3,311+

    The Adeline

    304 Lake Ave, Maitland, FL 32751
    (689) 219-8866
  14. Rent Special
    Rent Special
    STUDIO
    $1,726+
    1 BED
    $1,930+
    3 BEDS
    $3,444+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,638 - $3,356
    Required Monthly Fees$88
    Utilities & EssentialsVaries
    Total Monthly Price$1,726 - $3,444

    Vida at Health Village

    2680 N Orange Ave, Orlando, FL 32804
    (321) 621-2828
  16. Building Photo - 662 Callahan St
    2 BEDS, 1 BATH
    $2,499
    Total Monthly Price Total Monthly Price New
    Base Rent$2,499
    Required Monthly FeesNone
    Total Monthly Price$2,499

    662 Callahan St Unit SI ID1545989P

    662 Callahan St, Winter Park, FL 32789
  19. 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
  21. Building Photo - 102 W King St
    2 BEDS, 1 BATH
    $3,697
    Total Monthly Price Total Monthly Price New
    Base Rent$3,697
    Required Monthly FeesNone
    Total Monthly Price$3,697

    102 W King St Unit SI ID1029870P

    102 W King St, Orlando, FL 32804

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Winter Park at a Glance

Average Rent

$1,481
(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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Winter Park Apartments for Rent in Your Budget

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