UPS Delivery Driver Jobs in Winter Garden, FL — Start This Week

As of August 2026, there are 15 UPS delivery driver openings in Winter Garden, FL. Local pay ranges from $18 to $52/hr. Listings are updated daily — benefits start Day 1 for most positions.

UPS

Evening Role:Driver Opportunity(Winter Garden)

Winter Garden, FL

$21 - $42

UPS

Earn Extra Cash:Driver Opportunity(Winter Garden)

Winter Garden, FL

$23 - $30

UPS

Earn Extra Cash:Driver Opportunity(Winter Garden)

Winter Garden, FL

$25 - $44

UPS

Driver Opportunity(Gig)-Earn in Winter Garden

Winter Garden, FL

$18 - $21

UPS

Start ASAP:Driver Opportunity(Winter Garden)

Winter Garden, FL

$23 - $28

UPS

Flexible Hours:Driver Opportunity-Winter Garden

Winter Garden, FL

$21 - $42

UPS

Flexible Hours:Driver Opportunity-Winter Garden

Winter Garden, FL

$22 - $26

UPS

Start Today:Driver Opportunity(Winter Garden)

Winter Garden, FL

$21 - $28

UPS

(Winter Garden)Part-Time:Driver Opportunity

Winter Garden, FL

$36 - $52

UPS

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

Winter Garden, FL

$21 - $42

UPS

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

Winter Garden, FL

$18 - $21

UPS

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

Winter Garden, FL

$23 - $28

UPS Delivery Driver Jobs in Winter Garden — FAQ

How many UPS delivery driver jobs are open in Winter Garden, FL?
There are currently 15+ 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 15+ 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 Fulfillment Center Jobs in Winter Garden

20 open positions

UPS CDL Driver Jobs in Winter Garden

3 open positions

UPS Weekend Jobs in Winter Garden

1 open positions

Last updated: August 25, 2026