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Apartments for Rent in Winter Garden, FL under $2000


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  • Rent specials Rewards
    1 bd $1,729+
    Base rent
    Verified Listing

    Solay Horizon West

    4.5 (18)
    9005 Solay Road, Winter Garden, FL 34787
    Apply online • Pet friendly • Dishwasher
  • Rent specials
    1 bd $1,493+
    2 bd $1,651+
    Base rent
    Verified Listing

    Palm Crossing

    4.5 (14)
    1240 Winter Garden Vineland Rd, Winter Garden, FL 34787
    Apply online • Pet friendly
  • Rent specials 13 units available
    1 bd $1,514+
    2 bd $1,749+
    3 bd $1,949+
    Base rent Income restricted
    Verified Listing

    Country Gardens

    4.0 (6)
    15122 West Colonial Drive, Winter Garden, FL 34787
    Apply online • Pet friendly • Fitness center
  • More Rentals Near Winter Garden, FL

  • Rent specials
    1 bd $1,714+
    2 bd $1,858+
    Base rent
    4.5 (14)
    906 Oasis Palm Circle, Ocoee, FL 34761
    Apply online • Pet friendly • Parking
  • Rent specials Rewards
    Studio $1,533+
    1 bd $1,583+
    2 bd $1,993+
    Base rent
    Verified Listing

    The Overlook

    4.5 (4)
    15055 Lake Britt Circle, Winter Garden, FL 34787
    Apply online • Pet friendly • Fitness center
  • 17 units available
    1 bd $1,697+
    2 bd $1,862+
    Base rent
    4.0 (133)
    100 Maguire Park St, Ocoee, FL 34761
    Apply online • Pet friendly • Parking
  • Rent specials Rewards
    Studio $1,480
    1 bd $1,685+
    2 bd $1,945
    Base rent
    Verified Listing

    The Alibi At Lake Lilly

    4.5 (4)
    2760 Southside Drive, Ocoee, FL 34761
    Apply online • Pet friendly • Parking
  • 22 units available
    1 bd $1,339+
    2 bd $1,805+
    Base rent
    4.5 (260)
    2415 Treasure Landing Pkwy, Ocoee, FL 34761
    Apply online • Pet friendly • Parking
  • 1 bd $1,472+
    2 bd $1,924+
    Base rent
    Verified Listing

    Addison At Windermere

    4.5 (60)
    13644 Tortona Lane, Windermere, FL 34786
    Apply online • Pet friendly
  • Rent specials
    1 bd $1,098+
    2 bd $1,431+
    Base rent
    Verified Listing

    ARIUM Lakeview

    4.0 (17)
    1024 Vizcaya Lake Road, Ocoee, FL 34761
    Apply online • Pet friendly • Fitness center
  • 27 units available
    1 bd $1,500+
    2 bd $1,799+
    Base rent
    Verified Listing

    Arbours At Crown Point

    4.5 (104)
    1236 Arbour Point Way, Ocoee, FL 34761
    Apply online • Pet friendly • Pool
  • 1 bd $1,435+
    2 bd $1,735+
    Base rent
    Verified Listing

    Ellery At Lake Sherwood

    8008 Balasands Blvd, Orlando, FL 32818
    Pet friendly
  • Rent specials 10 units available
    2 bd $1,749
    3 bd $1,720+
    4 bd $1,954
    Base rent Income restricted
    1724 London Crest Drive, Orlando, FL 32818
    Apply online • Pet friendly • Parking
  • 4 units available
    2 bd $1,649+
    3 bd $1,999
    Base rent Income restricted
    Verified Listing

    Lake Sherwood

    3.0 (2)
    1724 London Crest Drive, Orlando, FL 32818
    Apply online • Pet friendly • Parking
  • 8 units available
    1 bd $1,216
    2 bd $946
    3 bd $1,625
    Base rent Income restricted
    Verified Listing

    Woodhill Apartments

    4.0 (4)
    7200 Woodhill Park Drive, Orlando, FL 32818
    Apply online • Pet friendly • Fitness center
  • 12 units available
    1 bd $1,528+
    2 bd $1,728+
    Base rent
    Verified Listing

    MAA Windermere

    4.0 (24)
    11598 Lachlan Lane, Windermere, FL 34786
    Apply online • Pet friendly • Parking
  • Rent specials 10 units available
    1 bd $1,626+
    Total monthly cost
    Verified Listing

    Venetian Isle

    4.5 (13)
    6506 San Francesco Way, Windermere, FL 34786
    Apply online • Pet friendly • Fitness center
  • Rent specials 14 units available
    1 bd $1,500+
    2 bd $1,845+
    Base rent
    Verified Listing

    MAA Crosswater

    4.5 (30)
    7826 Crosswater Trail, Windermere, FL 34786
    Apply online • Pet friendly • Parking
  • Rent specials 29 units available
    1 bd $1,436+
    2 bd $1,846+
    Base rent
    Verified Listing

    The Westerly

    3.5 (32)
    14680 Westerly Drive, Winter Garden, FL 34787
    Apply online • Pet friendly • Parking
  • Rent specials 25 units available
    1 bd $1,396+
    2 bd $1,608+
    Base rent
    Verified Listing

    Alvista Metrowest

    4.0 (23)
    2207 Lake Debra Drive, Orlando, FL 32835
    Apply online • Pet friendly • Parking
  • Rent specials
    Studio $1,599+
    1 bd $1,772+
    Base rent
    2317 Ocoee Apopka Road, Apopka, FL 32703
    Apply online • Pet friendly • Parking
  • 1 bd $1,216
    2 bd $1,375
    3 bd $1,688
    Base rent Income restricted
    Verified Listing

    Woodridge Apartments

    4.0 (14)
    7351 Woodridge Park Drive, Orlando, FL 32818
    Pet friendly • Parking • Fitness center
  • 1 bd $875
    Base rent
    Verified Listing

    704 Center Street

    704 Center Street, Ocoee, FL 34761
    In unit laundry • Dishwasher • Air conditioner
  • 1 bd $1,350
    Base rent
    2950 White Magnolia Loop, Clermont, FL 34711
    Pet friendly • In unit laundry • Air conditioner
  • 4-21-city



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 3 Nov 2026.

What are the best apartments in Winter Garden, FL?
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.

Apartments in Winter Garden, FL under $2,000

Balancing snug and cheap is no joke when it comes to renting a place to live. “Are there any apartments near me under $2,000?” is a great question to start from. Knowing your budget means you’re one step ahead and on the right track. We’ve taken care of the rest and found 255 apartments for rent in Winter Garden, FL on which you’ll spend less than $2,000. A small, cheap rental means you’ll have to budget your living space as well. The great news is that keeping it simple pays off in more than one way. The cost of utilities is likely to run low, and you get the added benefit of not having to spend too much time cleaning up the whole place. Smaller apartments are more likely to be closer to the city center, so there are potential cuts to your transportation costs too. And here’s one more very special secret to add to your book-of-perks: you’re less likely to overshop when you know your space is limited.

Rentals near you under $2,000

Our goal is to help you find cheap apartments that live up to your dreams without crushing your budget. It may be a long shot to go looking for 3 bedroom apartments or even 2 bedroom for less than $2,000. The average rental size in Winter Garden, FL is 1,019 Sqft, but the $2,000 limit will probably narrow your search to places with a smaller square footage. Go through our listings and be on the look-out for a hassle-free studio or a 1 bedroom apartment. We trust you’ll turn it into a cozy home which is also budget-friendly to the core.