Driving Jobs in Winter Haven, FL — See Openings

As of May 2026, there are 200+ open driving positions in Winter Haven, FL. Current pay ranges from $425 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.

Heavy Haul Last Mile

Student-Friendly Part-Time Heavy/bulky Item Delivery Specialist

Winter Haven, FL

$3,344 - $4,840

Uber

Winter Haven Career:Connect Package Delivery Driver at Uber | Hiring

Winter Haven, FL

$3,000 - $5,500

Campus Courier Network

Weekend Shift:Driver Opportunity-Winter Haven

Winter Haven, FL

$2,730 - $5,040

Shipt

Winter Haven Needs:Campus Area Shopper(Part-Time)

Winter Haven, FL

$2,600 - $4,800

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Winter Haven, FL

$3,080 - $5,500

Shipt

Early Morning Shopper(Part-Time)@ Shipt-Winter Haven

Winter Haven, FL

$2,200 - $3,800

Uber

Winter Haven Contractor Role:Ubereats Bicycle & Scooter Courier

Winter Haven, FL

$2,500 - $4,500

Corporate Transit Solutions

B2B Corporate Route Courier

Winter Haven, FL

$3,200 - $4,500

Instacart

Campus Area Instacart Delivery Driver

Winter Haven, FL

$2,808 - $5,184

Mechanic's Choice Transport

Automotive Parts Courier

Winter Haven, FL

$2,800 - $4,200

US Postal Service Contractors

Highway Contract Route (HCR) Driver

Winter Haven, FL

$3,520 - $6,160

Metro Pedal Express

Urban Bicycle Courier (Downtown Dispatch)

Winter Haven, FL

$2,500 - $4,000

Driving Jobs in Winter Haven — FAQ

How many driving jobs are available in Winter Haven, FL right now?
There are currently 200+ 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 200+ listings above and apply directly.

Last updated: May 03, 2026