Delivery Driver Jobs in Winter Garden, FL — Now Hiring

As of May 2026, there are 169 delivery driver openings in Winter Garden, FL. Local pay ranges from $500 to $9,180/year. Listings are updated daily — benefits start Day 1 for most positions.

On-Demand Tasks Network

Independent Contractor Driver-On-demand Errands($2k-$4k/Month)-Winter

Winter Garden, FL

$2,000 - $4,000

AquaDrop Delivery

Winter Garden Area Part-Time:Home Delivery Route Driver

Winter Garden, FL

$3,500 - $5,000

Uber

Winter Garden Ubereats Bicycle & Scooter Courier(Gig)

Winter Garden, FL

$2,500 - $4,500

Uber

Winter Garden Weekend Rideshare Driver($2k-$3.5k/Month) | Hiring

Winter Garden, FL

$2,000 - $3,500

Final Mile Delivery Co.

Winter Garden Independent Contractor Driver-Final Mile

Winter Garden, FL

$3,000 - $5,500

Auto Logistics Pros

Independent Contractor Driver-Auto Parts Courier Needed-Winter Garden

Winter Garden, FL

$2,380 - $4,080

Peak Season Logistics

Part-Time Seasonal Holiday Package Driver – Winter Garden

Winter Garden, FL

$3,500 - $5,000

Corporate Transit Solutions

B2B Corporate Route Courier

Winter Garden, FL

$3,200 - $4,500

Local Logistics Pros

Part-Time Local Package Delivery Driver(Winter Garden) | Part

Winter Garden, FL

$3,300 - $4,950

Uber

Winter Garden Night Shift Ubereats Courier(Gig)

Winter Garden, FL

$2,800 - $4,800

Uber

Part-time Ubereats Driver(lunch Rush)(Gig)-Winter Garden

Winter Garden, FL

$880 - $1,980

National Grocery Delivery Network

Student Friendly:Driver Opportunity(Winter Garden)

Winter Garden, FL

$2,500 - $4,500

Delivery Driver Jobs in Winter Garden — FAQ

How many delivery driver jobs are open in Winter Garden, FL?
There are currently 169+ delivery driver positions in Winter Garden, FL. New delivery driver roles are added regularly — check this page for the latest openings.
How much do delivery driver jobs pay in Winter Garden?
Delivery Driver pay in Winter Garden varies by employer, route type, and experience level. Many positions offer shift differentials, mileage bonuses, and sign-on bonuses. Browse the listings above to see pay details for each opening.
Do delivery driver jobs in Winter Garden require experience?
Many delivery driver positions in Winter Garden welcome entry-level applicants. Employers like Amazon, FedEx, and UPS often provide paid training. CDL positions may require a valid commercial license — check individual listings for specific requirements.
How do I apply for delivery driver jobs in Winter Garden?
Browse the 169+ delivery driver listings above, click on any position for full details including pay, schedule, and requirements, then follow the application link. Most driving positions have a simple online application.

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Other Driving Jobs in Winter Garden

Other Driving Jobs in Winter Garden

12 open positions

Part-Time Driving Jobs in Winter Garden

10 open positions

Cdl Driver Jobs in Winter Garden

3 open positions

Grocery Jobs in Winter Garden

2 open positions

DSP Driver Jobs in Winter Garden

2 open positions

Weekend Driving Jobs in Winter Garden

2 open positions

Last updated: May 03, 2026