Driving Jobs in Winter Haven, FL — See Openings

As of May 2026, there are 160+ open driving positions in Winter Haven, FL. Current pay ranges from $13 to $364,000 per year. Top hiring areas include Delivery Driver, Cdl Driver and General. New roles are posted daily — listings on this page are verified and updated regularly.

FedEx

Flexible Ground Delivery Driver(Winter Haven)

Winter Haven, FL

$18 - $22

GoPuff

$2.8k-$4.5k/Month Convenience Store Delivery Driver job in Winter

Winter Haven, FL

$2,800 - $4,500

Amazon DSP

Delivery Driver|Flexible|Winter Haven

Winter Haven, FL

$19 - $24

AAA Roadside

[Part-Time] Driver Opportunity-Winter Haven

Winter Haven, FL

$28 - $40

Quest Diagnostics

Medical Courier Delivery Driver

Winter Haven, FL

$2,548 - $3,822

Amazon Flex

Winter Haven Contract:Delivery Driver-Independent Contractor

Winter Haven, FL

$16 - $22

Old Dominion Freight Line

Winter Haven Needs:Driver Opportunity(Part-Time)

Winter Haven, FL

$80,000 - $95,000

Domino's Pizza

Pizza Delivery Driver

Winter Haven, FL

$2,200 - $3,696

Coach USA

Winter Haven,FL:Charter Bus Driver-CDL B With Passenger Endorsement at

Winter Haven, FL

$19 - $28

Auto Logistics Pros

Apply Today in Winter Haven:Independent Contractor Driver-Auto Parts

Winter Haven, FL

$2,800 - $4,800

Medline Industries

Medline Medical Supply Delivery Driver

Winter Haven, FL

$23 - $29

Walmart Spark

Walmart Spark Delivery Driver

Winter Haven, FL

$2,548 - $4,095

Driving Jobs in Winter Haven — FAQ

How many driving jobs are available in Winter Haven, FL right now?
There are currently 160+ 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 160+ listings above and apply directly.

Last updated: May 13, 2026