Driving Jobs in Winter Garden, FL — Immediate Openings

As of May 2026, there are 180+ 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 Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Final Mile Delivery Co.

Winter Garden Job:Independent Contractor Driver-Final Mile Parcel

Winter Garden, FL

$3,000 - $5,500

FedEx

Fedex seeks Delivery Driver in Winter Garden | Hiring

Winter Garden, FL

$4,024 - $7,474

Shipt

Urgent Hire in Winter Garden:Courier

Winter Garden, FL

$2,000 - $3,500

Uber

Weekend Rideshare Driver Position in Winter Garden | Hiring

Winter Garden, FL

$2,000 - $3,500

Uber

Winter Garden-based Uberx Driver Opening | Hiring

Winter Garden, FL

$3,000 - $5,000

Corporate Catering Couriers

Join Corporate Catering Couriers in Winter Garden as a Independent

Winter Garden, FL

$3,500 - $6,000

Grubhub

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

Winter Garden, FL

$2,600 - $4,800

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Winter Garden, FL

$2,520 - $4,410

DoorDash

DoorDash Drive (B2B/Merchant) Delivery Courier

Winter Garden, FL

$3,150 - $5,775

Uber

Night Shift Rideshare Driver•Winter Garden,FL•Uber | Hiring

Winter Garden, FL

$3,200 - $5,500

Corporate Catering Couriers

Independent Contractor Driver-Catering Logistics•Winter

Winter Garden, FL

$3,500 - $6,000

PepsiCo

Flexible Route Sales Delivery Driver(Winter Garden)

Winter Garden, FL

$4,500 - $7,000

Driving Jobs in Winter Garden — FAQ

How many driving jobs are available in Winter Garden, FL right now?
There are currently 180+ 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 180+ listings above and apply directly.

Last updated: May 04, 2026