Driving Jobs in Winter Haven, FL — Hiring Now

As of May 2026, there are 90+ open driving positions in Winter Haven, FL. Current pay ranges from $13 to $331,240 per year. Top hiring areas include Delivery Driver, Cdl Driver and Dsp. New roles are posted daily — listings on this page are verified and updated regularly.

DoorDash

Winter Haven,FL:Delivery Driver at Doordash | Hiring

Winter Haven, FL

$3,000 - $5,200

DoorDash

Catering Delivery Driver Position in Winter Haven | Hiring

Winter Haven, FL

$4,200 - $6,800

Uber Eats

Winter Haven Career:Night Shift Delivery Driver at Uber Eats | Hiring

Winter Haven, FL

$3,100 - $5,300

Uber Eats

Daily Pay Delivery Driver

Winter Haven, FL

$3,136 - $5,376

DoorDash

Work in Winter Haven:Morning Shift Delivery Driver | Hiring

Winter Haven, FL

$2,700 - $4,600

Domino's Pizza

Pizza Delivery Driver

Winter Haven, FL

$2,625 - $4,410

Instacart

Winter Haven,FL:Grocery Delivery Driver at Instacart | Hiring

Winter Haven, FL

$3,400 - $5,800

AutoZone

Auto Parts Delivery Driver

Winter Haven, FL

$2,520 - $3,780

DoorDash

Entry-Level Delivery Driver — No Experience Required

Winter Haven, FL

$2,200 - $3,800

Spark Driver

Winter Haven Contractor Role:Walmart Spark Delivery Driver

Winter Haven, FL

$13 - $19

DoorDash

Join Team:Delivery Driver-Dasher(Flexible,Winter Haven)

Winter Haven, FL

$15 - $26

Grubhub

Part-time Delivery Driver-Winter Haven,FL | Hiring

Winter Haven, FL

$600 - $1,800

Driving Jobs in Winter Haven — FAQ

How many driving jobs are available in Winter Haven, FL right now?
There are currently 90+ open driving positions in Winter Haven, 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 Haven?
Driving job pay in Winter Haven 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 Haven?
Yes. Many delivery driver, courier, and DSP positions in Winter Haven 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 Haven?
Driving jobs in Winter Haven 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 Haven?
Benefits vary by employer, but many driving positions in Winter Haven 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 Haven?
Your take-home pay as a driver in Winter Haven 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 Haven?
Yes, many driving positions in Winter Haven 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 90+ listings above and apply directly.

Last updated: May 10, 2026