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Apartments for Rent in Winter Garden, FL under $2000

164 Rentals Available
Apartments for Rent in Winter Garden, FL under $2000. 164 Rentals Available
  • a living room with blue chairs and a white coffee table
    Today

    9005 Solay Road, Winter Garden, FL 34787
    1 BED $1,729+
  • a living room with orange couches and a coffee table
    Today

    1240 Winter Garden Vineland Rd, Winter Garden, FL 34787
    1 BED $1,547+
    2 BEDS $1,728+
  • a living room with a couch and a kitchen with a sink
    Today

    1223 East Plant Street, Winter Garden, FL 34787
    STUDIO $1,773+
    1 BED $1,620+
  • a kitchen with black appliances and granite counter tops
    Today

    1030 Maxey Drive, Winter Garden, FL 34787
    4 BEDS $1,945
  • 150 move in cost on select 2 bedroom apartment homes starting at only 950
    Today

    15122 West Colonial Drive, Winter Garden, FL 34787
    Income Restricted
    1 BED $1,469+
    2 BEDS $1,735+
    3 BEDS $1,929
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  • More Rentals Near Winter Garden, FL

  • the lobby of a library with blue chairs and a yellow table
    Today

    15055 Lake Britt Circle, Winter Garden, FL 34787
    STUDIO $1,673
    1 BED $1,778+
  • a living room with a couch and a ceiling fan
    Today

    100 Maguire Park St, Ocoee, FL 34761
    1 BED $1,594+
    2 BEDS $1,908+
  • the living room has a stone fireplace and a large rug
    Today

    101 Casa Mirella Way, Windermere, FL 34786
    1 BED $1,675+
  • a living room with couches and a coffee table
    Today

    2760 Southside Drive, Ocoee, FL 34761
    STUDIO $1,620
    1 BED $1,750+
  • a living room with leather furniture and a fireplace
    Today

    906 Oasis Palm Circle, Ocoee, FL 34761
    1 BED $1,797+
  • a living room with a couch and a table
    Today

    2415 Treasure Landing Pkwy, Ocoee, FL 34761
    1 BED $1,474+
  • Interactive banner bedroom
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  • a living room with blue walls and a couch and a chair
    Today

    13644 Tortona Lane, Windermere, FL 34786
    1 BED $1,685+
  • a birds eye view of a house with a large pool
    Today

    1024 Vizcaya Lake Road, Ocoee, FL 34761
    1 BED $1,225+
    2 BEDS $1,720+
  • a large living room with couches and a table
    Today

    1236 Arbour Point Way, Ocoee, FL 34761
    1 BED $1,750
    2 BEDS Ask for pricing
  • a large living room with a table and chairs
    Today

    1724 London Crest Drive, Orlando, FL 32818
    Income Restricted
    2 BEDS $1,599
    3 BEDS $1,479
    4 BEDS $1,629
  • a living room with a couch and chairs and
    Today

    1724 London Crest Drive, Orlando, FL 32818
    Income Restricted
    2 BEDS $1,775
    3 BEDS Ask for pricing
  • a living room with blue chairs and a fireplace
    Today

    11598 Lachlan Lane, Windermere, FL 34786
    1 BED $1,563+
    2 BEDS $1,983+
  • a living room with chairs and a table
    Today

    7826 Crosswater Trail, Windermere, FL 34786
    1 BED $1,975+
  • a living room with a couch and a table
    Today

    14680 Westerly Drive, Winter Garden, FL 34787
    STUDIO $1,723+
    1 BED $1,655+
  • a living room with a couch and a ceiling fan
    Today

    2207 Lake Debra Drive, Orlando, FL 32835
    1 BED $1,615+
    2 BEDS $1,733+
  • a home with a lawn and a sidewalk in front of it
    Today

    3428 Westland Dr, Orlando, FL 32818
    3 BEDS $1,770
  • a spacious living room with carpet and a ceiling fan
    Today

    2376 Locke Ave, Orlando, FL 32818
    3 BEDS $1,995
  • a living room with a blue couch and a coffee table
    Today

    15000 Stratus Loop, Winter Garden, FL 34787
    1 BED $1,804+
  • a living room with couches and chairs in front of a brick wall
    Today

    2423 ARECA PALM DRIVE, APOPKA, FL 32703
    1 BED $1,625+
    2 BEDS $1,895+
  • a white house with a driveway and a garage door
    Today

    3307 Lake Tiny Cir, Orlando, FL 32818
    3 BEDS $1,835
5-20-city
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Getting around in Winter Garden, FL

34 /100
Car-Dependent
34 /100
Somewhat Bikeable
Walk Score®: 34, Bike Score®: 34

Frequently asked questions

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

Prices and availability in Winter Garden, FL were last updated on 8 Apr 2026.

What are the best apartments in Winter Garden, FL?

The best apartments in Winter Garden, FL are: Solay Horizon West, Palm Crossing, Vida Winter Garden, The Exchange and 1030 Maxey Drive Winter Garden, FL 34787.

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

In Winter Garden, 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 8% of Winter Garden's rentals, 49% are small-scale complexes with under 50 units, and 41% are single-family rentals.

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

Searching for apartments for rent in Winter Garden, 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 Garden, FL, where the average rent is $1,959 per month, there are 164 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 Garden, 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 Garden, FL going for $1,225 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!