Klebsiella pneumoniae is one of the most prevalent bacteria causing urinary tract infections (UTIs). Its increasing resistance to a wide array of antibiotics limits available treatment options. This study investigated the characteristics and trends of antimicrobial resistance in K. pneumoniae isolated from UTIs in Crete, Greece, during 2017 and 2022. Among the 11,946 Enterobacteriaceae isolated from urine specimens, a total of 1,771 K. pneumoniae isolates were identified (14.8%), with an isolation frequency secondary to Escherichia coli (66.3%). K. pneumoniae isolates increased over the years, with a peak in the year 2022. Higher resistance rates were detected in ciprofloxacin (41%), trimethoprim/sulfamethoxazole (TMP/SMX) (38.1%) and nitrofurantoin (33.9%). Resistance to ciprofloxacin, amoxicillin/clavulanic acid, tigecycline, and TMP/SMX significantly increased from 33.7%, 24%, 6%, and 33.1%, respectively, over the years 2017-2019, to 47.8%, 34.2%, 14.3% and 42.8%, respectively, over the period 2020-2022. ESBL production and carbapenem resistance were decreased by 2.2% and 3.7%, respectively, over the two three-year periods (2017-2019 and 2020-2022). Among the 278 carbapenem-resistant K.pneumoniae (CRKP) isolates, 164 (59%), 66 (23.7%), 18 (6.5%) and 16 (5.8%) were positive for KPC, NDM, VIM and OXA-48 enzymes, respectively. Only 14 (5%) isolates harboured two carbapenemase genes, namely 10 (3.6%) both blaNDM and blaVIM, and 4 (1.4%) both blaKPC and blaNDM. Females, inpatients and the elderly were more frequently affected by CRKP. The frequency of multidrug-resistant (MDR) and extensively drug-resistant (XDR) isolates were 32.6% and 7.7%, respectively. Continuous surveillance of local microbial prevalence and monitoring of antimicrobial resistance patterns provide critical information to guide the empiric therapy for UTIs and control the spread of MDR bacteria.