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

984 Rentals
.
  1. Building Photo - Atlas at Winter Park
    Good Value
    1 BED
    $1,249+
    2 BEDS
    $1,514+
    3 BEDS
    $2,002+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,224 - $1,977
    Required Monthly Fees$25
    Utilities & EssentialsVaries
    Total Monthly Price$1,249 - $2,002

    Atlas at Winter Park

    3733 N Goldenrod Rd, Winter Park, FL 32792
    (689) 219-8770
  5. $165 Off
    Price Drop. $165 Off
    1 BED
    $1,200+
    2 BEDS
    $1,485+
    3 BEDS
    $1,725+

    Signal Pointe

    2500 Howell Branch Rd, Winter Park, FL 32792
    (689) 220-5609
  7. Rent Special
    Rent Special
    STUDIO
    $1,600+
    1 BED
    $1,700+
    2 BEDS
    $1,475+
    3 BEDS
    $1,750+

    Hannibal Square

    433 W New England Ave, Winter Park, FL 32789
    (689) 207-3890
  9. $362 Off
    Price Drop. $362 Off
    1 BED
    $1,771+
    2 BEDS
    $1,864+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,681 - $2,110
    Required Monthly Fees$90
    Total Monthly Price$1,771 - $2,200

    Audubon Park

    990 Warehouse Rd, Orlando, FL 32803
    (689) 219-8885
  10. 1 BED, 1 BATH
    $1,700
    Total Monthly Price Total Monthly Price New
    Base Rent$1,700
    Required Monthly FeesNone
    Total Monthly Price$1,700

    1913 South Blvd Unit B

    1913 South Blvd, Maitland, FL 32751
    (689) 225-6561
  12. Building Photo - Kingswood Apartments
    Good Value
    STUDIO
    $900+
    1 BED
    $1,050+
    2 BEDS
    $1,200+
    3 BEDS
    $1,600+

    Kingswood Apartments

    1101 Lee Rd, Orlando, FL 32810
  17. 1 BED, 1 BATH
    $1,250

    2500 Lee Rd

    2500 Lee Rd, Winter Park, FL 32789
  20. 2 BEDS, 2 BATHS
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000

    155 Stefanik Rd

    155 Stefanik Rd, Winter Park, FL 32792
  21. 2 BEDS, 1 BATH
    $1,695
    Total Monthly Price Total Monthly Price New
    Base Rent$1,695
    Required Monthly FeesNone
    Total Monthly Price$1,695

    1720 Miller Ave

    1720 Miller Ave, Winter Park, FL 32789
  25. Building Photo - 162 Moyses Rd
    2 BEDS, 2 BATHS
    $1,895

    162 Moyses Rd

    162 Moyses Rd, Winter Park, FL 32792
  29. Building Photo - 452 Banyon Tree Cir
    1 BED, 1 BATH
    $1,125
    Total Monthly Price Total Monthly Price New
    Base Rent$1,125
    Required Monthly FeesNone
    Total Monthly Price$1,125

    452 Banyon Tree Cir Unit 200

    452 Banyon Tree Cir, Maitland, FL 32751
  30. Building Photo - 551 Flemming Way
    1 BED, 1 BATH
    $1,150
    Total Monthly Price Total Monthly Price New
    Base Rent$1,150
    Required Monthly FeesNone
    Total Monthly Price$1,150

    551 Flemming Way Unit 201

    551 Flemming Way, Maitland, FL 32751
  41. Building Photo - 276 Cambridge Blvd
    1 BED, 1 BATH
    $1,750
    Total Monthly Price Total Monthly Price New
    Base Rent$1,750
    Required Monthly FeesNone
    Total Monthly Price$1,750

    276 Cambridge Blvd

    276 Cambridge Blvd, Winter Park, FL 32789
    Apply
  42. Building Photo - 2924 Antique Oaks Cir
    2 BEDS, 2.5 BATHS
    $1,850
    Total Monthly Price Total Monthly Price New
    Base Rent$1,850
    Required Monthly FeesNone
    Total Monthly Price$1,850

    2924 Antique Oaks Cir Unit 48

    2924 Antique Oaks Cir, Winter Park, FL 32792
    Apply
Showing 42 of 183 results, Page 2 of 5

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

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 727 Sq Ft $1,536/mo
  • Fairview 741 Sq Ft $1,796/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.

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.