Driving Jobs in Winter Haven, FL — Immediate Openings

As of October 2026, there are 250+ open driving positions in Winter Haven, FL. Current pay ranges from $12 to $345,800 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.

Granite Construction

CDL B Water Truck Driver - Construction Site Dust Control

Winter Haven, FL

$29 - $35

Auto Logistics Pros

Independent Contractor Driver-Auto Parts Courier at Auto Logistics

Winter Haven, FL

$3,219 - $5,520

Mechanic's Choice Transport

Flexible Automotive Parts Courier(Winter Haven)

Winter Haven, FL

$2,800 - $4,200

Regional Auto Dealership Group

Part-Time Role in Winter Haven:OEM Dealership Auto Parts Delivery

Winter Haven, FL

$3,000 - $4,500

Secure Document Couriers

Weekend Shift:Driver Opportunity-Winter Haven

Winter Haven, FL

$2,800 - $5,000

AutoZone

Winter Haven,FL:Auto Parts Delivery Driver(local Hub)at Autozone

Winter Haven, FL

$2,940 - $4,410

AquaDrop Delivery

Winter Haven Full-time Home & Office Beverage Step Van Driver

Winter Haven, FL

$3,780 - $5,460

Bimbo Bakeries USA

Winter Haven Full-time Role:Bimbo Bakeries Box Truck Route Driver

Winter Haven, FL

$4,000 - $5,500

Amazon Flex

$21.50/hr Driver Opportunity-Winter Haven(PT)

Winter Haven, FL

$18 - $25

Corporate Catering Couriers

Part-Time Job at Corporate Catering Couriers:Independent Contractor

Winter Haven, FL

$3,500 - $6,000

Performance Foodservice

Performance Foodservice seeks CDL Class A Route Delivery Driver in

Winter Haven, FL

$70,000 - $90,000

PepsiCo

Beverage Distribution Box Truck Driver(Gig)-Winter Haven

Winter Haven, FL

$5,000 - $7,500

Driving Jobs in Winter Haven — FAQ

How many driving jobs are available in Winter Haven, FL right now?
There are currently 250+ 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 250+ listings above and apply directly.

Last updated: October 03, 2026