Driving Jobs in Winter Garden, FL — Open Positions

As of April 2026, there are 140+ open driving positions in Winter Garden, FL. Current pay ranges from $500 to $9,520 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.

Grubhub

Winter Garden Part-Time:Shop And Pay Driver(Now Hiring) | Part

Winter Garden, FL

$2,800 - $4,800

Instacart

Late Night Instacart Courier

Winter Garden, FL

$2,548 - $4,368

Final Mile Delivery Co.

Winter Garden Job:Independent Contractor Driver-Final Mile Parcel

Winter Garden, FL

$3,000 - $5,500

Shipt

Driver Opportunity needed in Winter Garden(Apply Now)

Winter Garden, FL

$2,500 - $4,500

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Winter Garden, FL

$3,360 - $6,160

Grubhub

Early Morning Grubhub Driver

Winter Garden, FL

$2,002 - $3,458

Uber

Uber is hiring a Night Shift Driver in Winter Garden | Apply Now

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

Grubhub

Part-Time Job in Winter Garden – Campus Area Driver | Part Time

Winter Garden, FL

$2,600 - $4,800

Uber

Part-time Driver($500-$1.5k/Month)-Winter Garden,FL | Hiring

Winter Garden, FL

$500 - $1,500

On-Demand Tasks Network

Independent Contractor Driver-On-demand Errands(Gig Economy And

Winter Garden, FL

$2,100 - $4,200

Local Shopper Partners

Courier needed in Winter Garden(Apply Now)

Winter Garden, FL

$1,900 - $3,325

Driving Jobs in Winter Garden — FAQ

How many driving jobs are available in Winter Garden, FL right now?
There are currently 140+ 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 140+ listings above and apply directly.

Last updated: April 26, 2026