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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 22 Feb 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 31% of the housing is rented out compared to 69% of homes are owned, according to the most recent Census Bureau estimates. 8% of Winter Garden's apartments are found in large buildings of 50 units or more, 48% are located in smaller apartment complexes with less than 50 units, and 42% are single-family rentals.

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

Are you looking for a smart space where you can easily combine comfort with convenience? You will surely find the property that perfectly fits your needs with this variety of options. RentCafe offers you 164 apartments for rent in Winter Garden, FL from 25 modern buildings, so you’ll certainly find something suitable for you. If you want to live alone or with your partner, you might want to look for a studio or browse through our selection of 1 bedroom apartments. If you need more space but you don’t want to spend more than necessary on a monthly rent, check out our 2 bedroom or 3 bedroom apartments for less than $2,000, and make the most out of your budget.

Finding the best rental near you

Winter Garden, FL is an amazing place to call home, with several rentals under $2,000 for you to choose from. There are many options and filters you can apply to your search to make the process easier and to find your next apartment faster and more efficiently. Asking yourself ‘are there any cheap apartments near me’? With our helpful filters, you can easily find the home of your dreams that also fits within your budget. With rent prices as low as $1,225 in Winter Garden, FL, you can find affordable and appealing apartments that match your requirements. Sort your search by ‘Rent’ ascending to see the cheapest ones at the top of the list. As soon as you find your perfect apartment, make sure to contact the property to check for availability or apply online directly on RentCafe.

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