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Apartments with Rent Specials Winter Park, FL

905 Rentals
.
  2. Building Photo - Gables Baldwin Park
    Rent Special
    Rent Special
    |
    STUDIO
    $2,316+
    1 BED
    $2,451+
    2 BEDS
    $3,113+
    3 BEDS
    $3,946+
    Total Monthly Price Total Monthly Price New
    Base Rent$2,268 - $8,250
    Required Monthly Fees$48
    Utilities & EssentialsVaries
    Total Monthly Price$2,316 - $4,541

    Gables Baldwin Park

    2050 Jake St, Orlando, FL 32814
    (470) 305-6691
  6. Rent Special
    Rent Special
    1 BED
    $1,306+
    2 BEDS
    $1,243+

    Seabrook

    3114 Terry Brook Dr, Winter Park, FL 32792
    (689) 220-5925
  8. 1 Month Free
    1 Month Free
    STUDIO
    $1,819+
    1 BED
    $1,944+
    2 BEDS
    $2,674+
    3 BEDS
    $3,280+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,795 - $3,274
    Required Monthly Fees$24
    Utilities & EssentialsVaries
    Total Monthly Price$1,819 - $3,298

    Enders Place at Baldwin Park

    4220 New Broad St, Orlando, FL 32814
    (689) 220-2141
  9. Rent Special
    Rent Special
    |
    1 BED
    $1,764+
    2 BEDS
    $2,093+
    3 BEDS
    $3,041+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,729 - $5,957
    Required Monthly Fees$35
    Utilities & EssentialsVaries
    Total Monthly Price$1,764 - $3,041

    The Village at Lake Lily

    925 S Orlando Ave, Maitland, FL 32751
    (689) 219-5267
  17. 2 Months Free
    2 Months Free
    STUDIO
    $1,775+
    1 BED
    $1,815+
    2 BEDS
    $2,375+
    3 BEDS
    $2,994+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,700 - $3,255
    Required Monthly Fees$75
    Total Monthly Price$1,775 - $3,330

    Aurora on the Trail

    825 McCullough Ave, Orlando, FL 32803
    (689) 219-5368
  18. Rent Special
    Rent Special
    STUDIO
    $1,730+
    1 BED
    $1,965+
    2 BEDS
    $2,665+
    3 BEDS
    $3,487+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,642 - $6,735
    Required Monthly Fees$88
    Utilities & EssentialsVaries
    Total Monthly Price$1,730 - $3,623

    Vida at Health Village

    2680 N Orange Ave, Orlando, FL 32804
    (321) 621-2828
  23. 2 Months Free
    2 Months Free
    1 BED
    $2,022+
    2 BEDS
    $2,460+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,827 - $2,691
    Required Monthly Fees$195
    Utilities & EssentialsVaries
    Total Monthly Price$2,022 - $2,886

    Rosalia Winter Park 55+ Active Adult Community

    3045 Aloma Ave, Winter Park, FL 32792
    (321) 320-8654
  30. Building Photo - Kingswood Apartments
    Rent Special
    Rent Special
    STUDIO
    $900+
    1 BED
    $1,050+
    2 BEDS
    $1,200+
    3 BEDS
    $1,600+

    Kingswood Apartments

    1101 Lee Rd, Orlando, FL 32810
  32. Building Photo - 1917 Truman Rd
    Discounts
    Discounts
    2 BEDS, 2 BATHS
    $1,450

    1917 Truman Rd

    1917 Truman Rd, Orlando, FL 32807
  33. Rent Special
    Rent Special
    1 BED
    $1,155+
    2 BEDS
    $1,451+
    3 BEDS
    $1,741+

    Venue At Winter Park

    5 Autumn Breeze Way, Winter Park, FL 32792
  35. 2 Months Free
    2 Months Free
    1 BED
    $1,349

    Indigo Winter Park

    220 S Semoran Blvd, Winter Park, FL 32792
  36. Welcome to Azure Winter Park - Azure Winter Park
    Rent Special
    Rent Special
    STUDIO
    $1,049+
    1 BED
    $1,249+
    2 BEDS
    $1,349+
    3 BEDS
    $2,199+

    Azure Winter Park

    3650 Summer Wind Dr, Winter Park, FL 32792
  37. Kitchen - Serena Winter Park
    2 Months Free
    2 Months Free
    1 BED
    $1,099+
    2 BEDS
    $1,519+

    Serena Winter Park

    2890 Red Lion Sq, Winter Park, FL 32792
  38. 1 Month Free
    1 Month Free
    1 BED
    $1,699+
    2 BEDS
    $1,899+

    The Fisher

    2001 Glenridge Way, Winter Park, FL 32792
  39. 2 Months Free
    2 Months Free
    1 BED
    $1,369+
    2 BEDS
    $1,349+
    3 BEDS
    $1,899+

    Sapphire Winter Park

    1743 Semoran North Cir, Winter Park, FL 32792

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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 738 Sq Ft $1,559/mo
  • Fairview 739 Sq Ft $1,879/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

Specialty Housing

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Winter Park Apartments for Rent in Your Budget

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