Note: Properties with the Total Monthly Price badge include all required fees. Tap the badge for more details.
-

Bedrooms

Bathrooms

Deals & Discount Filters
All Filters

Deals & Discounts

Price Range

–

Beds & Baths

Beds

Baths

Home Type

Pet Policy

Interior & Community Amenities

Speciality Housing

Keyword Search

Luxury Apartments for Rent in Winter Park, FL

394 Rentals
.
  1. 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
  3. |
    1 BED
    $1,668+
    2 BEDS
    $1,998+
    3 BEDS
    $2,156+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,584 - $3,428
    Required Monthly Fees$84
    Utilities & EssentialsVaries
    Total Monthly Price$1,668 - $3,512

    Cortland Lake Howell

    1280 Vinings Ln, Casselberry, FL 32707
    (321) 710-4674
  5. $198 Off
    Price Drop. $198 Off
    |
    1 BED
    $1,667+
    2 BEDS
    $2,247+
    3 BEDS
    $3,054+

    The Adeline

    304 Lake Ave, Maitland, FL 32751
    (689) 219-8866
  7. $291 Off
    Price Drop. $291 Off
    1 BED
    $2,046+
    2 BEDS
    $3,169+
    3 BEDS
    $3,692+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,989 - $4,642
    Required Monthly Fees$57
    Utilities & EssentialsVaries
    Total Monthly Price$2,046 - $4,699

    Baldwin Harbor

    1771-1887 Jake St, Orlando, FL 32814
    (689) 207-3563
  8. $383 Off
    Price Drop. $383 Off
    |
    1 BED
    $1,724+
    2 BEDS
    $2,093+
    3 BEDS
    $3,037+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,689 - $6,509
    Required Monthly Fees$35
    Utilities & EssentialsVaries
    Total Monthly Price$1,724 - $3,069

    The Village at Lake Lily

    925 S Orlando Ave, Maitland, FL 32751
    (689) 219-5267
  12. 1 Month Free
    1 Month Free
    STUDIO
    $1,730+
    1 BED
    $1,965+
    2 BEDS
    $2,455+
    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
  15. Building Photo - 662 Callahan St
    2 BEDS, 1 BATH
    $2,409
    Total Monthly Price Total Monthly Price New
    Base Rent$2,409
    Required Monthly FeesNone
    Total Monthly Price$2,409

    662 Callahan St Unit SI ID1545989P

    662 Callahan St, 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. Pool #1 on the Lake - 2912 Plaza Terrace Dr
    2 BEDS, 2 BATHS
    $2,695
    Total Monthly Price Total Monthly Price New
    Base Rent$2,695
    Required Monthly FeesNone
    Total Monthly Price$2,695

    2912 Plaza Terrace Dr

    2912 Plaza Terrace Dr, Orlando, FL 32803
    Apply

Can't find what you are looking for?

Clear All Filters

Winter Park at a Glance

Average Rent

$1,483
(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 737 Sq Ft $1,560/mo
  • Fairview 738 Sq Ft $1,876/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

Choose by Amenities

Winter Park Apartments for Rent in Your Budget

tooltips


I would like to...
0 out of 400 characters
By clicking above, you agree we may pass along your info so this property or the property’s affiliates can email, call, text, or autodial you to follow up and for any purpose. You also agree to... By clicking above, you agree we may pass along your info so this property or the property’s affiliates can email, call, text, or autodial you to follow up and for any purpose. You also agree to Apartmentfinder.com’s Privacy Statement and Terms of Service. Consent is not a condition for services. Message and data rates may apply. Read More Read Less

Submitting Request

Thank You

Your email has been sent.

Learn about our ratings.