Driving Jobs in Winter Haven, FL — Hiring Now

As of March 2026, there are 80+ open driving positions in Winter Haven, FL. Current pay ranges from $500 to $7,500 per year. Top hiring areas include Delivery Driver, General and Grocery. New roles are posted daily — listings on this page are verified and updated regularly.

National Grocery Delivery Network

Winter Haven Job:Driver Opportunity(No Exp Req*)

Winter Haven, FL

$2,500 - $4,500

FreshDrop Logistics

[Part-Time] Driver Opportunity-Winter Haven

Winter Haven, FL

$3,000 - $5,500

Local Shopper Partners

Winter Haven Job:Courier(No Exp Req*)

Winter Haven, FL

$2,000 - $3,500

Suburban Delivery Network

Flexible Hours:Driver Opportunity-Winter Haven

Winter Haven, FL

$2,800 - $4,800

Morning Express Couriers

Urgent Hire in Winter Haven:Driver Opportunity

Winter Haven, FL

$2,200 - $3,800

Midnight Logistics

$43.75/hr Late Night Convenience & Grocery Courier-Winter Haven(PT)

Winter Haven, FL

$2,800 - $4,800

Wholesale Transit Partners

Flexible Hours:Driver Opportunity-Winter Haven

Winter Haven, FL

$3,200 - $5,500

Midday Logistics Co.

[Part-Time] Driver Opportunity-Winter Haven

Winter Haven, FL

$950 - $1,900

Urban Pedal Logistics

[Fresh] Courier-Winter Haven(PT)

Winter Haven, FL

$2,500 - $4,500

Campus Courier Network

[Just Posted] Driver Opportunity-Winter Haven(PT)

Winter Haven, FL

$2,600 - $4,800

Grubhub

Part-Time Early Morning Driver Job – Winter Haven Hiring Now

Winter Haven, FL

$2,200 - $3,800

Grubhub

Part-Time Campus Area Driver – Winter Haven,FL | Part Time Job

Winter Haven, FL

$2,600 - $4,800

Driving Jobs in Winter Haven — FAQ

How many driving jobs are available in Winter Haven, FL right now?
There are currently 80+ 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 80+ listings above and apply directly.

Last updated: March 13, 2026