Driving Jobs in Winter Garden, FL — Open Positions

As of March 2026, there are 80+ open driving positions in Winter Garden, FL. Current pay ranges from $500 to $7,500 per year. Top hiring areas include Delivery Driver, General and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

National Grocery Delivery Network

Weekend Shift:Driver Opportunity-Winter Garden

Winter Garden, FL

$2,500 - $4,500

FreshDrop Logistics

$46.50/hr Driver Opportunity-Winter Garden(PT)

Winter Garden, FL

$2,850 - $5,225

Local Shopper Partners

Winter Garden Needs:Courier(Part-Time)

Winter Garden, FL

$2,100 - $3,675

Suburban Delivery Network

Weekend Shift:Driver Opportunity-Winter Garden

Winter Garden, FL

$2,660 - $4,560

Morning Express Couriers

[Fresh] Driver Opportunity-Winter Garden(PT)

Winter Garden, FL

$2,310 - $3,990

Midnight Logistics

[Fresh] Late Night Convenience & Grocery Courier-Winter Garden(PT)

Winter Garden, FL

$2,940 - $5,040

Wholesale Transit Partners

Student Friendly:Driver Opportunity(Winter Garden)

Winter Garden, FL

$3,200 - $5,500

Midday Logistics Co.

Winter Garden Job:Driver Opportunity(No Exp Req*)

Winter Garden, FL

$1,000 - $2,000

Urban Pedal Logistics

Winter Garden Needs:Courier(Part-Time)

Winter Garden, FL

$2,500 - $4,500

Campus Courier Network

Winter Garden Job:Driver Opportunity(No Exp Req*)

Winter Garden, FL

$2,600 - $4,800

Grubhub

Part-Time Early Morning Driver(Winter Garden,FL)|Grubhub | Part

Winter Garden, FL

$2,200 - $3,800

Grubhub

Recent Job:Part-Time Campus Area Driver – Winter Garden | Part

Winter Garden, FL

$2,600 - $4,800

Driving Jobs in Winter Garden — FAQ

How many driving jobs are available in Winter Garden, FL right now?
There are currently 80+ 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 80+ listings above and apply directly.

Last updated: March 13, 2026