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

As of October 2026, there are 42 UPS delivery driver openings in Winter Haven, FL. Local pay ranges from $15 to $50/hr. Listings are updated daily — benefits start Day 1 for most positions.

UPS

UPS Driver Helper — Entry-Level, No License Required

Winter Haven, FL

$16 - $19

UPS

Winter Haven Career:Weekend Delivery Driver—Weekdays Always Free at

Winter Haven, FL

$23 - $30

UPS

Part-Time Personal Vehicle Driver—Use Your Own Car,Flexible Hours

Winter Haven, FL

$21 - $25

UPS

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

Winter Haven, FL

$21 - $42

UPS

Driver Helper—Entry-level,No License Required(Contract)-Winter

Winter Haven, FL

$15 - $17

UPS

(Winter Haven)Part-Time:Driver Opportunity

Winter Haven, FL

$21 - $42

UPS

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

Winter Haven, FL

$18 - $21

UPS

Earn Extra Cash:Driver Opportunity(Winter Haven)

Winter Haven, FL

$21 - $25

UPS

UPS Weekend Delivery Driver — Weekdays Always Free

Winter Haven, FL

$20 - $26

UPS

UPS Delivery Driver — $42 Per Hour Top Rate, Full Benefits

Winter Haven, FL

$19 - $38

UPS

Package Car Driver—Full-time Driving Career(Gig)-Winter Haven

Winter Haven, FL

$28 - $42

UPS

Part-time Air Driver—Early Morning Flights,Done By

Winter Haven, FL

$26 - $32

UPS Delivery Driver Jobs in Winter Haven — FAQ

How many UPS delivery driver jobs are open in Winter Haven, FL?
There are currently 42+ 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 42+ 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.

UPS Delivery Driver Jobs in Other Cities

UPS Delivery Driver Jobs in Springfield

209 open positions

UPS Delivery Driver Jobs in Columbus

162 open positions

UPS Delivery Driver Jobs in Columbia

150 open positions

UPS Delivery Driver Jobs in Lakewood

149 open positions

UPS Delivery Driver Jobs in Greenville

142 open positions

UPS Delivery Driver Jobs in Bloomington

138 open positions

UPS Delivery Driver Jobs in Franklin

132 open positions

UPS Delivery Driver Jobs in Auburn

130 open positions

UPS Delivery Driver Jobs in Middletown

126 open positions

UPS Delivery Driver Jobs in Albany

125 open positions

Other UPS Jobs in Winter Haven

UPS Part-Time Jobs in Winter Haven

118 open positions

UPS Fulfillment Center Jobs in Winter Haven

82 open positions

UPS Warehouse Jobs in Winter Haven

38 open positions

UPS Overnight Jobs in Winter Haven

23 open positions

UPS Sortation Center Jobs in Winter Haven

17 open positions

UPS Manager Jobs in Winter Haven

17 open positions

UPS CDL Driver Jobs in Winter Haven

15 open positions

UPS Other UPS Jobs in Winter Haven

12 open positions

Last updated: October 16, 2026