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

As of September 2026, there are 16 UPS delivery driver openings in Winter Garden, FL. Local pay ranges from $17 to $50/hr. Listings are updated daily — benefits start Day 1 for most positions.

UPS

$31.50/hr Driver Opportunity-Winter Garden(PT)

Winter Garden, FL

$21 - $42

UPS

[Flex] Driver Opportunity-Winter Garden

Winter Garden, FL

$21 - $28

UPS

Student Friendly:Driver Opportunity(Winter Garden)

Winter Garden, FL

$23 - $30

UPS

Winter Garden Needs:Driver Opportunity(Part-Time)

Winter Garden, FL

$24 - $42

UPS

Part-Time Role in Winter Garden:Driver Helper—Entry-level,No

Winter Garden, FL

$18 - $21

UPS

$24.25/hr Driver Opportunity-Winter Garden(PT)

Winter Garden, FL

$22 - $26

UPS

Flexible Hours:Driver Opportunity-Winter Garden

Winter Garden, FL

$35 - $50

UPS

[Flex] Driver Opportunity-Winter Garden

Winter Garden, FL

$17 - $19

UPS

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

Winter Garden, FL

$21 - $25

UPS

Package Car Driver—Full-time Driving Career|Part-Time Job|Winter

Winter Garden, FL

$28 - $42

UPS

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

Winter Garden, FL

$21 - $42

UPS

Hiring in Winter Garden:Driver Opportunity(Part-Time)

Winter Garden, FL

$21 - $26

UPS Delivery Driver Jobs in Winter Garden — FAQ

How many UPS delivery driver jobs are open in Winter Garden, FL?
There are currently 16+ UPS delivery driver positions in Winter Garden, 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 Garden?
UPS delivery driver pay in Winter Garden 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 Garden?
Many UPS delivery driver positions in Winter Garden 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 Garden?
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 Garden

UPS Part-Time Jobs in Winter Garden

48 open positions

UPS Fulfillment Center Jobs in Winter Garden

31 open positions

UPS Warehouse Jobs in Winter Garden

21 open positions

UPS Manager Jobs in Winter Garden

10 open positions

UPS Other UPS Jobs in Winter Garden

10 open positions

UPS Overnight Jobs in Winter Garden

9 open positions

UPS Sortation Center Jobs in Winter Garden

7 open positions

UPS Weekend Jobs in Winter Garden

4 open positions

Last updated: September 29, 2026