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

Apartments for Rent in Winter Park, FL under $2000

Apartments for Rent in Winter Park, FL under $2000. 203 Rentals Available
203 Rentals Available
Quick filters
  • a kitchen with black appliances and a white counter top
    Only 3 units left
    1 bd $1,500
    Base rent
    Verified Listing

    1512 Indiana Avenue, Winter Park, FL 32789
    Apply online • Pet friendly
  • a living room with a couch and a table
    1 bd $1,138
    2 bd $1,339
    Base rent Income restricted
    Verified Listing

    550 N. Denning Drive, Winter Park, FL 32789
    Pet friendly

  • More Rentals Near Winter Park, FL

  • a living room with a couch and a table
    20 units available
    Studio $1,860+
    1 bd $1,818+
    Base rent
    Verified Listing

    1305 Morgan Stanley Ave, Winter Park, FL 32789
    Apply online • Pet friendly
  • a living room with furniture and a ceiling fan
    4 units available
    1 bd $1,745+
    Base rent
    Verified Listing

    3045 Aloma Avenue, Winter Park, FL 32792
    Apply online • Pet friendly
  • a living room with a gray couch and a blue chair
    Only 3 units left
    1 bd $1,942+
    Base rent
    Verified Listing

    4460 Lower Park Road, Orlando, FL 32814
    Apply online • Pet friendly
  • a living room with couches and chairs and a tv
    18 units available
    Studio $1,685+
    1 bd $1,760+
    Base rent
    Verified Listing

    741 Clay Street, Winter Park, FL 32789
    Apply online • Pet friendly
  • a living room with a couch and a table
    1 bd $1,320+
    2 bd $1,480+
    Base rent
    Verified Listing

    3250 Bishop Park Dr, Winter Park, FL 32792
    Apply online • Pet friendly
  • an open kitchen and living room with a table and chairs
    14 units available
    Studio $1,608+
    1 bd $1,788+
    Base rent
    Verified Listing

    1874 Harmon Avenue, Winter Park, FL 32789
    Apply online • Pet friendly
  • an open kitchen and living room with a table and chairs
    12 units available
    1 bd $1,788+
    Base rent
    Verified Listing

    190 Independence Lane, Maitland, FL 32751
    Apply online • Pet friendly
  • a living room with a couch and a table and a sliding glass
    21 units available
    1 bd $1,450+
    2 bd $1,625
    Base rent
    Verified Listing

    3250 Whisper Lake Lane, Winter Park, FL 32792
    Apply online • Pet friendly
  • a living room with couches and chairs and a television
    Rent specials 13 units available
    1 bd $1,840+
    Base rent
    Verified Listing

    4688 New Broad Street, Orlando, FL 32814
    Apply online • Pet friendly
  • a living room with couches and chairs and a tv on the wall
    1 bd $1,091
    2 bd $1,286
    Base rent Income restricted
    Verified Listing

    525 Sybelia Pkwy, Maitland, FL 32751
    Pet friendly
  • an aerial view of a courtyard in a building with trees and plants
    Rent specials
    Studio $1,667+
    1 bd $1,906+
    Base rent
    Verified Listing

    2680 North Orange, Orlando, FL 32804
    Apply online • Pet friendly
  • the living room and dining room of a home with a table and chairs
    Only 2 units left
    1 bd $1,450
    2 bd $1,600
    3 bd $2,000
    Base rent
    Verified Listing

    541 Oak Reserve Lane, Winter Park, FL 32792
    Apply online • Pet friendly
  • a living room with a couch and a table
    Studio $1,773
    1 bd $1,717
    Base rent
    Verified Listing

    2650 Dade Ave, Orlando, FL 32804
    Apply online • Pet friendly
  • a living room and kitchen with a couch and a table
    1 bd $1,664+
    Base rent
    Verified Listing

    955 N Orlando Ave, Maitland, FL 32751
    Apply online • Pet friendly
  • a living room with a couch and a ceiling fan
    8 units available
    1 bd $1,649+
    2 bd $1,786+
    Base rent
    Verified Listing

    4220 New Broad Street, Orlando, FL 32814
    Apply online • Pet friendly
  • a kitchen with white appliances and a sink and stove
    35 units available
    1 bd $1,420+
    2 bd $1,629+
    3 bd $1,987+
    Base rent
    Verified Listing

    5800 Auvers Blvd, Orlando, FL 32807
    Apply online • Pet friendly
  • a living room with a couch and a coffee table and a tv
    11 units available
    1 bd $1,750+
    2 bd $1,995+
    Base rent
    Verified Listing

    4000 Maguire Blvd, Orlando, FL 32803
    Apply online • Pet friendly
  • a kitchen and living room with a large island and a table with chairs
    Studio $1,695+
    1 bd $1,830+
    Base rent
    Verified Listing

    9264 Moss Preserve Pkwy., Orlando, FL 32832
    Apply online • Pet friendly
  • a kitchen with a sink and a refrigerator
    11 units available
    1 bd $1,300+
    2 bd $1,605+
    Base rent
    Verified Listing

    1166 Pointe Newport Terrace Drive, Casselberry, FL 32707
    Pet friendly
  • a living room with a couch and a ceiling fan
    10 units available
    1 bd $1,440+
    2 bd $1,721+
    Base rent
    Verified Listing

    3935 Sutton Place Blvd, Winter Park, FL 32792
    Apply online • Pet friendly
  • a living room with couches and tables and large windows
    Only 2 units left
    1 bd $1,655+
    Base rent
    Verified Listing

    7490 Dwell Well Way, Winter Park, FL 32792
    Apply online • Pet friendly
  • a small blue house with a lawn and trees
    Only 1 unit left
    2 bd $1,875
    Base rent
    Verified Listing

    903 Eldridge St, Orlando, FL 32803
    Apply online • Pet friendly
  • a large living room with couches and a tv
    8 units available
    Studio $1,690+
    1 bd $1,823+
    Base rent
    Verified Listing

    601 Trelago Way, Maitland, FL 32751
    Apply online • Pet friendly
2-23-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 26 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.