Save search
Skip the filters. Search with AI Mode instead.

Apartments for Rent in Winter Garden, FL under $2000

Apartments for Rent in Winter Garden, FL under $2000. 209 Rentals Available
209 Rentals Available
Quick filters
  • Rent specials
    1 bd $1,604+
    Base rent
    Verified Listing

    4.5 (14)
    9005 Solay Road, Winter Garden, FL 34787
    Apply online • Pet friendly • Dishwasher
  • a living room with two orange couches and a fireplace
    Rent specials
    1 bd $1,491+
    2 bd $1,671+
    Base rent
    Verified Listing

    4.5 (13)
    1240 Winter Garden Vineland Rd, Winter Garden, FL 34787
    Apply online • Pet friendly
  • a living room and dining room with a table and chairs
    Rent specials 15 units available
    1 bd $1,449
    2 bd $1,599+
    3 bd $1,899
    Base rent Income restricted
    Verified Listing

    4.0 (6)
    15122 West Colonial Drive, Winter Garden, FL 34787
    Apply online • Pet friendly
  • A kitchen with a sink and a dishwasher.
    3 bd $2,000
    Base rent
    Verified Listing

    224 W. Cypress Street, Winter Garden, FL 34787

  • More Rentals Near Winter Garden, FL

  • a living room with leather furniture and a fireplace
    1 bd $1,549+
    2 bd $1,982+
    Base rent
    Verified Listing

    4.5 (14)
    906 Oasis Palm Circle, Ocoee, FL 34761
    Apply online • Pet friendly • Parking
  • a living room with a couch and a coffee table
    Rent specials Rewards
    Studio $1,728
    1 bd $1,753+
    Base rent
    Verified Listing

    4.5 (4)
    15055 Lake Britt Circle, Winter Garden, FL 34787
    Apply online • Pet friendly
  • a living room with a couch and a ceiling fan
    Rent specials 7 units available
    1 bd $1,617+
    Base rent
    Verified Listing

    4.0 (127)
    100 Maguire Park St, Ocoee, FL 34761
    Apply online • Pet friendly
  • a living room with couches and a coffee table
    Rent specials Rewards
    Studio $1,480
    1 bd $1,690+
    2 bd $1,890
    Base rent
    Verified Listing

    4.5 (4)
    2760 Southside Drive, Ocoee, FL 34761
    Apply online • Pet friendly
  • a living room with a couch and a table
    Rent specials 39 units available
    1 bd $1,571+
    2 bd $1,743+
    3 bd $1,816+
    Base rent
    Verified Listing

    4.5 (244)
    2415 Treasure Landing Pkwy, Ocoee, FL 34761
    Apply online • Pet friendly
  • a living room with blue walls and a couch and a chair
    Rent specials
    1 bd $1,697+
    Base rent
    Verified Listing

    4.5 (60)
    13644 Tortona Lane, Windermere, FL 34786
    Apply online • Pet friendly
  • a living room with a couch and a table
    1 bd $1,097+
    2 bd $1,548+
    Base rent
    Verified Listing

    4.0 (17)
    1024 Vizcaya Lake Road, Ocoee, FL 34761
    Apply online • Pet friendly
  • A living room with brown leather couches and a coffee table.
    26 units available
    1 bd $1,550+
    2 bd $1,750+
    3 bd $2,000+
    Base rent
    Verified Listing

    4.5 (102)
    1236 Arbour Point Way, Ocoee, FL 34761
    Apply online • Pet friendly
  • a large living room with a table and chairs
    4 units available
    2 bd $1,749
    3 bd $1,590+
    4 bd $1,931
    Base rent Income restricted
    Verified Listing

    1724 London Crest Drive, Orlando, FL 32818
    Apply online • Pet friendly
  • A modern living room with a dining table and a couch.
    6 units available
    1 bd $1,216
    2 bd $1,461
    3 bd $1,688
    Base rent Income restricted
    Verified Listing

    4.0 (14)
    7351 Woodridge Park Drive, Orlando, FL 32818
    Apply online • Pet friendly
  • A kitchen with a white counter and blue chairs.
    Rent specials 17 units available
    1 bd $1,448+
    2 bd $1,783+
    Base rent
    Verified Listing

    4.5 (22)
    11598 Lachlan Lane, Windermere, FL 34786
    Apply online • Pet friendly
  • A kitchen with a white counter top and a brown stool.
    Rent specials 26 units available
    1 bd $1,493+
    2 bd $1,934+
    Total monthly cost
    Verified Listing

    4.5 (13)
    6506 San Francesco Way, Windermere, FL 34786
    Apply online • Pet friendly
  • a large living room with chairs and tables and a fireplace
    Rent specials 5 units available
    1 bd $1,775+
    Base rent
    Verified Listing

    4.5 (28)
    7826 Crosswater Trail, Windermere, FL 34786
    Apply online • Pet friendly
  • 3426 Westland Dr 2 Beds Apartment for Rent
    Only 1 unit left
    2 bd $1,580
    Base rent
    Verified Listing

    3426 Westland Dr, Orlando, FL 32818
    Apply online • Pet friendly
  • A modern kitchen with a dining table and chairs.
    Rent specials
    Studio $1,718+
    1 bd $1,772+
    Base rent
    Verified Listing

    2317 Ocoee Apopka Road, Apopka, FL 32703
    Apply online • Pet friendly
  • a living room with a couch and a table
    Rent specials 13 units available
    1 bd $1,575+
    2 bd $1,790+
    Base rent
    Verified Listing

    4.0 (22)
    2423 ARECA PALM DRIVE, APOPKA, FL 32703
    Apply online • Pet friendly
  • A living room with a grey couch and a patterned armchair.
    8 units available
    Ask for pricing
    Income restricted
    Verified Listing

    4.0 (4)
    7200 Woodhill Park Drive, Orlando, FL 32818
    Apply online • Pet friendly
  • a living room with a couch and chairs and
    Ask for pricing
    Income restricted
    Verified Listing

    3.0 (2)
    1724 London Crest Drive, Orlando, FL 32818
    Pet friendly
  • A living room with a grey couch and a coffee table.
    Ask for pricing
    Income restricted
    Verified Listing

    8825 Buena Pl, Windemere, FL 34786
    Pet friendly
  • A kitchen area with a refrigerator and cabinets.
    2 bd $1,600
    Base rent
    Verified Listing

    6312 Raleigh St, Orlando, FL 32835
    Pet friendly
  • A kitchen with white cabinets and a stainless steel refrigerator.
    2 bd $1,700
    Base rent
    Verified Listing

    6016 Westgate Dr, Orlando, FL 32811
    Pet friendly
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 24 May 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.