UPS Delivery Driver Jobs in Winter Haven, FL — See Openings

As of September 2026, there are 16 UPS delivery driver openings in Winter Haven, FL. Local pay ranges from $18 to $50/hr. Listings are updated daily — benefits start Day 1 for most positions.

UPS

Evening Role:Driver Opportunity(Winter Haven)

Winter Haven, FL

$22 - $44

UPS

[Part-Time] Driver Opportunity-Winter Haven

Winter Haven, FL

$23 - $30

UPS

Evening Role:Driver Opportunity(Winter Haven)

Winter Haven, FL

$22 - $39

UPS

(Winter Haven)Driver Opportunity-Contract/Gig

Winter Haven, FL

$18 - $21

UPS

Urgent Hire in Winter Haven:Driver Opportunity

Winter Haven, FL

$24 - $29

UPS

(Winter Haven)Part-Time:Driver Opportunity

Winter Haven, FL

$21 - $42

UPS

Earn Extra Cash:Driver Opportunity(Winter Haven)

Winter Haven, FL

$21 - $25

UPS

Driver Opportunity(Gig)-Earn in Winter Haven

Winter Haven, FL

$22 - $29

UPS

$42.50/hr Driver Opportunity-Winter Haven(PT)

Winter Haven, FL

$35 - $50

UPS

Delivery Driver—$42 Per Hour Top Rate,Full Benefits|Part-Time

Winter Haven, FL

$21 - $42

UPS

Immediate Part-Time Weekend Delivery Driver—Weekdays Always Free

Winter Haven, FL

$23 - $30

UPS

Weekend Part-Time Driver Helper—Entry-level,No License Required –

Winter Haven, FL

$18 - $21

UPS Delivery Driver Jobs in Winter Haven — FAQ

How many UPS delivery driver jobs are open in Winter Haven, FL?
There are currently 16+ UPS delivery driver positions in Winter Haven, FL. New delivery driver roles are added regularly — check this page for the latest openings.
How much do UPS delivery driver jobs pay in Winter Haven?
UPS delivery 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 delivery driver positions with no experience in Winter Haven?
Many UPS delivery 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 delivery driver jobs in Winter Haven?
Browse the 16+ delivery 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

31 open positions

UPS Warehouse Jobs in Winter Haven

12 open positions

UPS Fulfillment Center Jobs in Winter Haven

10 open positions

UPS Overnight Jobs in Winter Haven

7 open positions

UPS Sortation Center Jobs in Winter Haven

5 open positions

UPS Manager Jobs in Winter Haven

3 open positions

UPS CDL Driver Jobs in Winter Haven

3 open positions

UPS Weekend Jobs in Winter Haven

2 open positions

Last updated: September 10, 2026