Driving Jobs in Winter Haven, FL — See Openings

As of September 2026, there are 40+ open driving positions in Winter Haven, FL. Current pay ranges from $14 to $128,800 per year. Top hiring areas include Delivery Driver, Cdl Driver and Overnight. New roles are posted daily — listings on this page are verified and updated regularly.

Atlas Van Lines

CDL A Household Goods Mover Truck Driver

Winter Haven, FL

$89,250 - $115,500

Stevens Trucking

CDL A Livestock Hauler Truck Driver - Cattle Transport

Winter Haven, FL

$95,200 - $128,800

AAA Roadside

CDL B Tow Truck Driver - Heavy Duty Recovery

Winter Haven, FL

$29 - $42

Waste Management

CDL B Garbage Truck Driver - Residential Refuse

Winter Haven, FL

$26 - $34

Cersosimo Lumber Company

CDL A Log Truck Driver - Forestry Hauler

Winter Haven, FL

$28 - $36

Heavy Legacy LLC

CDL A Frac Sand Driver - Oilfield West Texas

Winter Haven, FL

$79,200 - $110,000

SCC Concrete

CDL B Truck Driver - Ready Mix Concrete Mixer

Winter Haven, FL

$28 - $36

Staker Parson Companies

CDL A Dump Truck Driver - Local Aggregate Hauling

Winter Haven, FL

$27 - $34

Old Dominion Freight Line

CDL A Truck Driver - LTL Pickup and Delivery

Winter Haven, FL

$70,400 - $83,600

J.B. Hunt Intermodal

CDL A Truck Driver - Intermodal Container Drayage

Winter Haven, FL

$66,000 - $83,600

Regional Expedite Logistics

Earn Extra Cash:Driver Opportunity(Winter Haven)

Winter Haven, FL

$3,500 - $6,000

Urban Pedal Logistics

$42.50/hr Driver Opportunity-Winter Haven(PT)

Winter Haven, FL

$2,625 - $4,725

Driving Jobs in Winter Haven — FAQ

How many driving jobs are available in Winter Haven, FL right now?
There are currently 40+ 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 40+ listings above and apply directly.

Last updated: September 09, 2026