Delivery Driver Jobs in Winter Garden, FL — Apply Today

As of March 2026, there are 125 delivery driver openings in Winter Garden, FL. Local pay ranges from $500 to $9,350/year. Listings are updated daily — benefits start Day 1 for most positions.

Uber

Winter Garden Contract:Ubereats Large Order Delivery Driver

Winter Garden, FL

$3,500 - $6,000

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Winter Garden, FL

$2,576 - $4,600

Grubhub

Local Part-Time Part-time Driver(lunch Rush)Job – Winter Garden

Winter Garden, FL

$800 - $1,800

DoorDash

Suburban Route DoorDash Driver

Winter Garden, FL

$2,208 - $3,864

Urban Pedal Logistics

Urgent Hire:Independent Contractor Driver-Urban E-bike/scooter Courier

Winter Garden, FL

$2,500 - $4,500

Local Merchant Delivery Network

Independent Contractor Driver-Early Morning

Winter Garden, FL

$2,400 - $4,200

Regional Expedite Logistics

Winter Garden Independent Contractor Driver-Long Distance / Regional

Winter Garden, FL

$3,500 - $6,000

Wholesale Transit Partners

Student Friendly:Driver Opportunity(Winter Garden)

Winter Garden, FL

$3,200 - $5,500

Grubhub

Part-Time Grubhub Driver (Lunch Rush)

Winter Garden, FL

$736 - $1,656

Uber

Part-time Ubereats Driver(lunch Rush)Position in Winter Garden

Winter Garden, FL

$800 - $1,800

Corporate Catering Couriers

Winter Garden-based Independent Contractor Driver-Catering Logistics

Winter Garden, FL

$3,500 - $6,000

Uber

Recent Job Opening:Connect Package Delivery Driver(Winter Garden)

Winter Garden, FL

$3,000 - $5,500

Delivery Driver Jobs in Winter Garden — FAQ

How many delivery driver jobs are open in Winter Garden, FL?
There are currently 125+ 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 125+ 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

14 open positions

Part-Time Driving Jobs in Winter Garden

5 open positions

Grocery Jobs in Winter Garden

3 open positions

Weekend Driving Jobs in Winter Garden

1 open positions

Warehouse Jobs in Winter Garden

1 open positions

Cdl Driver Jobs in Winter Garden

1 open positions

Last updated: March 23, 2026