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Apartments for Rent in Winter Park, FL under $2000

Apartments for Rent in Winter Park, FL under $2000. 165 Rentals Available
165 Rentals Available
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  • A living room with a white sofa and a wooden coffee table.
    19 units available
    1 bd $1,469+
    2 bd $1,473+
    3 bd $1,872+
    Base rent
    Verified Listing

    4.0 (15)
    1701 Lee Road, Winter Park, FL 32789
    Apply online • Pet friendly
  • an open living room and dining room with a table and chairs
    Only 1 unit left
    2 bd $1,995
    Base rent
    Verified Listing

    Units 1,2,3,4, Winter Park, FL 32792
    Apply online • Pet friendly
  • A living room with a stone fireplace and a television above it.
    Only 1 unit left
    1 bd $1,344
    2 bd $1,586
    Base rent Income restricted
    Verified Listing

    550 N. Denning Drive, Winter Park, FL 32789
    Apply online • Pet friendly
  • A living room with a white couch and blue chairs.
    1 bd $1,797+
    Base rent
    Verified Listing

    4.0 (6)
    940 W. Canton Avenue, Winter Park, FL 32789
    Apply online • Pet friendly
  • A kitchen with a sink and a ceiling fan.
    1 bd $1,300
    Base rent
    Verified Listing

    1695 Lee Rd, Winter Park, FL 32789
    Pet friendly
  • A kitchen with a granite counter top and wooden floors.
    2 bd $1,850
    Base rent
    Verified Listing

    1500 Gay Road, Winter Park, FL 32789

  • More Rentals Near Winter Park, FL

  • an open kitchen and living room with a table and chairs
    6 units available
    1 bd $1,893+
    Base rent
    Verified Listing

    4.5 (9)
    190 Independence Lane, Maitland, FL 32751
    Apply online • Pet friendly • Parking
  • a living room and kitchen with a couch and a table
    Rent specials
    1 bd $1,721+
    Base rent
    Verified Listing

    4.5 (19)
    955 N Orlando Ave, Maitland, FL 32751
    Apply online • Pet friendly • Pool
  • A living room with blue chairs and a fireplace.
    Rent specials 32 units available
    1 bd $1,295+
    2 bd $1,690
    Total monthly cost
    Verified Listing

    3250 Whisper Lake Ln, Winter Park, FL 32792
    Apply online • Pet friendly • Air conditioner
  • the living room and dining room of a home with a table and chairs
    Rent specials Only 1 unit left
    1 bd $1,295+
    2 bd $1,495+
    Base rent
    Verified Listing

    4.5 (5)
    541 Oak Reserve Lane, Winter Park, FL 32792
    Pet friendly • Parking • Fitness center
  • A living room with a grey sofa and a white coffee table.
    Rent specials
    Studio $1,858+
    Base rent
    Verified Listing

    4.0 (2)
    1305 Morgan Stanley Ave, Winter Park, FL 32789
    Apply online • Pet friendly
  • A living room with a yellow couch and a wooden coffee table.
    10 units available
    1 bd $1,300+
    2 bd $1,400
    3 bd $1,850
    Base rent
    Verified Listing

    4.0 (110)
    3040 Aloma Avenue, WINTER PARK, FL 32792
    Apply online • Pet friendly
  • a living room with a gray couch and a blue chair
    Rent specials
    1 bd $1,908+
    Base rent
    Verified Listing

    4.5 (15)
    4460 Lower Park Road, Orlando, FL 32814
    Apply online • Pet friendly
  • a living room with couches and chairs and a tv
    Rent specials 8 units available
    Studio $1,585+
    1 bd $1,695+
    Base rent
    Verified Listing

    4.5 (30)
    741 Clay Street, Winter Park, FL 32789
    Apply online • Pet friendly
  • a living room with a couch and a table
    1 bd $1,314+
    2 bd $1,664+
    Base rent
    Verified Listing

    4.5 (7)
    3250 Bishop Park Dr, Winter Park, FL 32792
    Apply online • Pet friendly
  • an open kitchen and living room with a table and chairs
    Rent specials 16 units available
    Studio $1,550+
    1 bd $1,692+
    Base rent
    Verified Listing

    4.0 (13)
    1874 Harmon Avenue, Winter Park, FL 32789
    Apply online • Pet friendly
  • a living room with couches and chairs and a television
    Rent specials 28 units available
    1 bd $1,715+
    Base rent
    Verified Listing

    4.0 (45)
    4688 New Broad Street, Orlando, FL 32814
    Apply online • Pet friendly
  • a living room with couches and chairs and a tv on the wall
    Only 1 unit left
    1 bd $1,291
    2 bd $1,347+
    Base rent Income restricted
    Verified Listing

    4.0 (13)
    525 Sybelia Pkwy, Maitland, FL 32751
    Apply online • Pet friendly
  • a living room with a pool table and couches
    Rent specials
    Studio $1,630+
    1 bd $1,984+
    Total monthly cost
    Verified Listing

    4.0 (2)
    2680 North Orange, Orlando, FL 32804
    Apply online • Pet friendly
  • a living room with a couch and a table
    16 units available
    Studio $1,559+
    1 bd $1,756+
    Base rent
    Verified Listing

    3.5 (12)
    2650 Dade Avenue, Orlando, FL 32804
    Apply online • Pet friendly
  • a living room with a couch and tables in front of windows
    Rent specials
    Studio $1,695+
    1 bd $1,770+
    Base rent
    Verified Listing

    4.5 (24)
    9264 Moss Preserve Pkwy., Orlando, FL 32832
    Apply online • Pet friendly
  • A living room with a white couch and a painting on the wall.
    Rent specials
    1 bd $1,375+
    2 bd $1,599+
    Base rent
    Verified Listing

    4.0 (91)
    1166 Pointe Newport Terrace Drive, Casselberry, FL 32707
    Apply online • Pet friendly
  • a living room with a couch and a ceiling fan
    6 units available
    1 bd $1,431+
    2 bd $1,913+
    Base rent
    Verified Listing

    4.5 (22)
    3935 Sutton Place Blvd, Winter Park, FL 32792
    Apply online • Pet friendly
  • A living room with a grey couch and a television.
    Only 1 unit left
    Studio $1,934+
    Base rent
    Verified Listing

    4.5 (2)
    295 NE Ivanhoe Blvd., Orlando, FL 32804
    Apply online • Pet friendly
  • A kitchen with white cabinets and a wooden island.
    1 bd $1,875
    Base rent
    Verified Listing

    1308 Lake Baldwin Ln, Orlando, FL 32814
    Pet friendly
6-19-city

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 27 May 2026.

What are the best apartments in Winter Park, FL?
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 32% of Winter Park's rentals, 45% are small-scale complexes with under 50 units, and 23% are single-family rentals.