UPS CDL Driver Jobs in Winter Haven, FL — Now Hiring

As of October 2026, there are 15 UPS cdl driver openings in Winter Haven, FL. Local pay ranges from $21 to $55/hr. Listings are updated daily — benefits start Day 1 for most positions.

UPS

UPS CDL Apprentice Driver — Earn Your CDL While You Work

Winter Haven, FL

$21 - $36

UPS

Winter Haven CDL Apprentice Driver—Earn Your CDL While You Work

Winter Haven, FL

$25 - $45

UPS

UPS Seasonal Driver — No CDL Required, Immediate Start

Winter Haven, FL

$21 - $28

UPS

UPS Feeder Driver — CDL Class A Tractor-Trailer Career

Winter Haven, FL

$38 - $55

UPS

Winter Haven:Feeder Driver—CDL Class A Tractor-trailer Career

Winter Haven, FL

$35 - $50

UPS

Now Hiring:Feeder Driver—CDL Class A Tractor-trailer Career

Winter Haven, FL

$32 - $46

UPS

Student-Friendly Part-Time Seasonal Driver—No CDL

Winter Haven, FL

$21 - $28

UPS

Winter Haven Part-Time Job:Feeder Driver—CDL Class A

Winter Haven, FL

$35 - $50

UPS

Seasonal Driver—No CDL Required,Immediate Start Position in Winter

Winter Haven, FL

$21 - $28

UPS

UPS Feeder Driver — CDL Class A Tractor-Trailer Career

Winter Haven, FL

$38 - $55

UPS

Winter Haven Temporary Role:Seasonal Driver—No CDL

Winter Haven, FL

$21 - $28

UPS

UPS CDL Apprentice Driver — Earn Your CDL While You Work

Winter Haven, FL

$22 - $38

UPS CDL Driver Jobs in Winter Haven — FAQ

How many UPS cdl driver jobs are open in Winter Haven, FL?
There are currently 15+ UPS cdl driver positions in Winter Haven, FL. New cdl driver roles are added regularly — check this page for the latest openings.
How much do UPS cdl driver jobs pay in Winter Haven?
UPS cdl driver pay in Winter Haven varies by specific role and shift. Most positions include shift differentials for nights and weekends, plus benefits starting Day 1. Browse the listings above to see pay details for each opening.
Does UPS hire for cdl driver positions with no experience in Winter Haven?
Many UPS cdl driver positions in Winter Haven require no prior experience. UPS provides paid training for new hires. Check individual listings for specific requirements.
How do I apply for UPS cdl driver jobs in Winter Haven?
Browse the 15+ cdl driver listings above, click on any position for full details including pay and shift times, then follow the application link. Most UPS positions have a 15–30 minute online application.

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Other UPS Jobs in Winter Haven

UPS Part-Time Jobs in Winter Haven

118 open positions

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UPS Other UPS Jobs in Winter Haven

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Last updated: October 16, 2026