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

Apartments under $2,000 for Rent in Winter Park, FL

1,074 Rentals
.
  5. |
    1 BED
    $1,852
    Total Monthly Price Total Monthly Price New
    Base Rent$1,719 - $1,900
    Required Monthly Fees$133
    Total Monthly Price$1,852 - $2,033

    Vintage Winter Park Apartments

    7490 Dwell Well Way, Winter Park, FL 32792
    (689) 220-1305
  9. Rent Special
    Rent Special
    1 BED
    $1,291+
    2 BEDS
    $1,473+

    Seabrook

    3114 Terry Brook Dr, Winter Park, FL 32792
    (689) 220-5925
  11. |
    1 BED
    $1,732
    Total Monthly Price Total Monthly Price New
    Base Rent$1,648 - $1,768
    Required Monthly Fees$84
    Utilities & EssentialsVaries
    Total Monthly Price$1,732 - $1,852

    Cortland Lake Howell

    1280 Vinings Ln, Casselberry, FL 32707
    (321) 710-4674
  14. $250 Off
    Price Drop. $250 Off
    |
    1 BED
    $1,598
    Total Monthly Price Total Monthly Price New
    Base Rent$1,563 - $2,188
    Required Monthly Fees$35
    Utilities & EssentialsVaries
    Total Monthly Price$1,598 - $2,223

    The Village at Lake Lily

    925 S Orlando Ave, Maitland, FL 32751
    (689) 219-5267
  16. 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
  30. $194 Off
    Price Drop. $194 Off
    STUDIO
    $1,831+
    1 BED
    $1,669+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,594 - $1,821
    Required Monthly Fees$75
    Total Monthly Price$1,669 - $1,896

    Aurora on the Trail

    825 McCullough Ave, Orlando, FL 32803
    (689) 219-5368
  32. 1 BED
    $1,745
    Total Monthly Price Total Monthly Price New
    Base Rent$1,703
    Required Monthly Fees$42
    Utilities & EssentialsVaries
    Total Monthly Price$1,745

    400 North

    400 N Orlando Ave, Maitland, FL 32751
    (689) 219-4863
  33. Rent Special
    Rent Special
    STUDIO
    $1,667+
    1 BED
    $1,987+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,579 - $2,073
    Required Monthly Fees$88
    Utilities & EssentialsVaries
    Total Monthly Price$1,667 - $2,161

    Vida at Health Village

    2680 N Orange Ave, Orlando, FL 32804
    (321) 621-2828
  34. $350 Off
    Price Drop. $350 Off
    1 BED
    $999+
    2 BEDS
    $1,299+

    Soraya

    1485 Ash Cir, Casselberry, FL 32707
    (689) 205-8365
  38. 1 BED
    $1,482+
    2 BEDS
    $1,670+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,462 - $1,986
    Required Monthly Fees$20
    Utilities & EssentialsVaries
    Total Monthly Price$1,482 - $2,006

    Atlas at Winter Park

    3733 N Goldenrod Rd, Winter Park, FL 32792
    (689) 219-8770
  41. $348 Off
    Price Drop. $348 Off
    1 BED
    $1,317+
    2 BEDS
    $1,824+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,199 - $1,903
    Required Monthly Fees$118
    Utilities & EssentialsVaries
    Total Monthly Price$1,317 - $2,021

    Solis at Winter Park

    7502 Sun Key Blvd, Winter Park, FL 32792
    (321) 366-6748
  42. 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
Showing 42 of 173 results, Page 1 of 5

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

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.