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Apartments for Rent in Winter Park, FL under $2000

203 Rentals Available
Apartments for Rent in Winter Park, FL under $2000. 203 Rentals Available
  • a kitchen with black appliances and a white counter top
    Today

    1512 Indiana Avenue, Winter Park, FL 32789
    1 BED $1,500
  • a living room with a couch and a table
    Today

    550 N. Denning Drive, Winter Park, FL 32789
    Income Restricted
    1 BED $1,138
    2 BEDS $1,339

  • More Rentals Near Winter Park, FL

  • a living room with a couch and a table
    Today

    1305 Morgan Stanley Ave, Winter Park, FL 32789
    STUDIO $1,860+
    1 BED $1,818+
  • a living room with furniture and a ceiling fan
    Today

    3045 Aloma Avenue, Winter Park, FL 32792
    1 BED $1,745+
  • a living room with a gray couch and a blue chair
    Today

    4460 Lower Park Road, Orlando, FL 32814
    1 BED $1,942+
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  • a living room with couches and chairs and a tv
    Today

    741 Clay Street, Winter Park, FL 32789
    STUDIO $1,685+
    1 BED $1,760+
  • a living room with a couch and a table
    Today

    3250 Bishop Park Dr, Winter Park, FL 32792
    1 BED $1,320+
    2 BEDS $1,480+
  • an open kitchen and living room with a table and chairs
    Today

    1874 Harmon Avenue, Winter Park, FL 32789
    STUDIO $1,608+
    1 BED $1,788+
  • an open kitchen and living room with a table and chairs
    Today

    190 Independence Lane, Maitland, FL 32751
    1 BED $1,788+
  • a living room with a couch and a table and a sliding glass
    Today

    3250 Whisper Lake Lane, Winter Park, FL 32792
    1 BED $1,450+
    2 BEDS $1,625
  • a living room with couches and chairs and a television
    Today

    4688 New Broad Street, Orlando, FL 32814
    1 BED $1,840+
  • Interactive banner bedroom
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  • a living room with couches and chairs and a tv on the wall
    Today

    525 Sybelia Pkwy, Maitland, FL 32751
    Income Restricted
    1 BED $1,091
    2 BEDS $1,286
  • an aerial view of a courtyard in a building with trees and plants
    Today

    2680 North Orange, Orlando, FL 32804
    STUDIO $1,667+
    1 BED $1,906+
    2 BEDS Ask for Pricing
  • the living room and dining room of a home with a table and chairs
    Today

    541 Oak Reserve Lane, Winter Park, FL 32792
    1 BED $1,450
    2 BEDS $1,600
    3 BEDS $2,000
  • a living room with a couch and a table
    Today

    2650 Dade Ave, Orlando, FL 32804
    STUDIO $1,773
    1 BED $1,717
  • a living room and kitchen with a couch and a table
    Today

    955 N Orlando Ave, Maitland, FL 32751
    1 BED $1,664+
    2 BEDS Ask for Pricing
  • a living room with a couch and a ceiling fan
    Today

    4220 New Broad Street, Orlando, FL 32814
    1 BED $1,649+
    2 BEDS $1,786+
  • a kitchen with white appliances and a sink and stove
    Today

    5800 Auvers Blvd, Orlando, FL 32807
    1 BED $1,420+
    2 BEDS $1,629+
    3 BEDS $1,987+
  • a living room with a couch and a coffee table and a tv
    Today

    4000 Maguire Blvd, Orlando, FL 32803
    1 BED $1,750+
    2 BEDS $1,995+
  • a kitchen and living room with a large island and a table with chairs
    Today

    9264 Moss Preserve Pkwy., Orlando, FL 32832
    STUDIO $1,695+
    1 BED $1,830+
  • a kitchen with a sink and a refrigerator
    Today

    1166 Pointe Newport Terrace Drive, Casselberry, FL 32707
    1 BED $1,300+
    2 BEDS $1,605+
  • a living room with a couch and a ceiling fan
    Today

    3935 Sutton Place Blvd, Winter Park, FL 32792
    1 BED $1,440+
    2 BEDS $1,721+
  • a living room with couches and tables and large windows
    Today

    7490 Dwell Well Way, Winter Park, FL 32792
    1 BED $1,655+
  • a small blue house with a lawn and trees
    Today

    903 Eldridge St, Orlando, FL 32803
    2 BEDS $1,875
  • a large living room with couches and a tv
    Today

    601 Trelago Way, Maitland, FL 32751
    STUDIO $1,690+
    1 BED $1,823+
2-23-city
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Getting around in Winter Park, FL

25 /100
Car-Dependent
32 /100
Some Transit
31 /100
Somewhat Bikeable
Walk Score®: 25, Transit Score®: 32, Bike Score®: 31

Frequently asked questions

When were prices and availability in Winter Park, FL last updated?

Prices and availability in Winter Park, FL were last updated on 21 Feb 2026.

What are the best apartments in Winter Park, FL?

The best apartments in Winter Park, FL are: Paseo at Winter Park Village, 1055 S Kentucky Ave, Indiana Ave. Triplex, San Jose Apartments and Village Park Senior Living.

What type of rental buildings are in Winter Park, FL?

In Winter Park, 34% of the residents are renting compared to 66% owning a home, according to data from the U.S. Census Bureau. Large-scale apartment buildings with more than 50 units represent 28% of Winter Park's rentals, 49% are small-scale complexes with under 50 units, and 23% are single-family rentals.

Renting apartments in Winter Park, FL under $2,000

Searching for apartments for rent in Winter Park, FL under $2,000 is not an easy task, but luckily you have come to the right place. Whether you are a student on a budget, a young professional on the move, or simply a frugal person, RentCafe can help you find what you are looking for. Just make sure you know what you consider non-negotiable and what you can compromise on. Your new home is just a few clicks away. In Winter Park, FL, where the average rent is $2,203 per month, there are 203 units available for less than $2,000. Click on any of these units to see pictures, floor plans, amenities and more. After you have picked your favorite, you can contact the property to check availability. Considering that you are trying to spend as little as possible, looking at 1 bedroom apartments and studio apartments might be a good idea.

We’ll help you find the cheapest rental near you

Finding a nice cheap apartment is by no means impossible. You just have to be patient. Your “apartments near me under $2,000” search can bear fruit sooner than you think if you look carefully and check our site often. You never know when discount deals and special offers might pop up. Keep in mind that you are not the only one looking for an affordable apartment in Winter Park, FL. Choose “Save Search” to receive the latest apartments available directly to your inbox. This way, you will be able to stay one step ahead of the competition. With the cheapest apartments in Winter Park, FL going for $1,091 per month, there are great deals waiting to be discovered. Feeling lucky? Expand your search to 2 bedroom apartments and 3 bedroom apartments as well for more space.

Finding a home nearby is easier than you think. Check out our Apartments Near Me page and take your pick!