Driving Jobs in Winter Garden, FL — Immediate Openings

As of April 2026, there are 230+ open driving positions in Winter Garden, FL. Current pay ranges from $500 to $10,000 per year. Top hiring areas include Delivery Driver, General and Cdl Driver. New roles are posted daily — listings on this page are verified and updated regularly.

Local Logistics Network

Winter Garden Independent Contractor Driver-Medical Courier

Winter Garden, FL

$3,000 - $5,000

Lyft

Winter Garden Contractor Airport Transfer Driver | Hiring

Winter Garden, FL

$3,500 - $5,500

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Winter Garden, FL

$2,500 - $4,500

Grubhub

Part-Time Bicycle & Scooter Courier(Winter Garden) | Part Time

Winter Garden, FL

$2,500 - $4,500

FedEx Ground Independent Contractor

Winter Garden Needs:Driver Opportunity(Part-Time)

Winter Garden, FL

$3,800 - $5,700

National Grocery Delivery Network

Weekend Shift:Driver Opportunity-Winter Garden

Winter Garden, FL

$2,500 - $4,500

Mobile Tool Networks

Mobile Tool Sales Route Driver(Part-Time)-Winter Garden

Winter Garden, FL

$4,500 - $8,000

Uber

New Black Driver @ Uber in Winter Garden | Hiring

Winter Garden, FL

$4,500 - $7,500

Mechanic's Choice Transport

Automotive Parts Courier

Winter Garden, FL

$2,800 - $4,200

DoorDash

Night Shift DoorDash Driver (Late Night Logistics)

Winter Garden, FL

$2,800 - $4,800

PepsiCo

Winter Garden Flexible Role:Route Sales Delivery Driver

Winter Garden, FL

$4,500 - $7,000

Weekend Transit Co.

Student-Friendly Part-Time Weekend Parcel Delivery Driver in

Winter Garden, FL

$1,724 - $2,875

Driving Jobs in Winter Garden — FAQ

How many driving jobs are available in Winter Garden, FL right now?
There are currently 230+ open driving positions in Winter Garden, FL. These include delivery drivers, CDL truck drivers, couriers, bus drivers, DSP drivers, and local route positions. New jobs are added daily.
How much do driving jobs pay in Winter Garden?
Driving job pay in Winter Garden varies by role: Delivery drivers earn $18–$25/hr, CDL truck drivers $55K–$90K+/year, couriers $16–$22/hr, and bus drivers $20–$30/hr. Night and weekend routes often pay premium rates.
Can I get a driving job with no experience in Winter Garden?
Yes. Many delivery driver, courier, and DSP positions in Winter Garden require no prior experience and provide paid training. Delivery driver positions require a valid driver's license but no CDL. Some carriers offer free CDL training programs.
What schedules do driving jobs offer in Winter Garden?
Driving jobs in Winter Garden offer flexible schedules: day routes (6 AM–4 PM), evening routes (1 PM–10 PM), overnight/line haul (6 PM–6 AM), and weekend-only schedules (Fri–Sun or Sat–Mon). Part-time and gig-style shifts are also available. Overnight and weekend routes typically pay premium rates.
What benefits do driving jobs offer in Winter Garden?
Benefits vary by employer, but many driving positions in Winter Garden offer: health, dental, and vision insurance; 401(k) or retirement plans; paid time off; sign-on bonuses; weekly or daily pay; company-provided vehicles for delivery positions; and CDL training assistance from select employers.
How much do drivers take home after taxes in Winter Garden?
Your take-home pay as a driver in Winter Garden depends on your pay rate, hours worked, and state tax rate. For example, a delivery driver earning $22/hr in a no-tax state like Texas takes home about $750/week, while in California it's closer to $670/week after state tax.
Are driving companies hiring immediately in Winter Garden?
Yes, many driving positions in Winter Garden are hiring immediately with start dates within 1–2 weeks of applying. Delivery driver and courier roles often offer same-week start dates. Browse the 230+ listings above and apply directly.

Last updated: April 17, 2026