Driving Jobs in Winter Haven, FL — Hiring Now

As of October 2026, there are 50+ open driving jobs in Winter Haven, FL. Current pay ranges from $22 to $135,000 per year. Top hiring areas include Delivery Driver, Owner Operator and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Final Mile Delivery Co.

Start ASAP:Final Mile Parcel(Winter Haven)

Winter Haven, FL

$3,000 - $5,500

Regional Expedite Logistics

Weekend Shift:Driver Opportunity-Winter Haven

Winter Haven, FL

$3,500 - $6,000

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Winter Haven, FL

$4,550 - $7,735

United Parcel Service (UPS)

UPS Package Delivery Driver

Winter Haven, FL

$3,680 - $6,900

Corporate Catering Couriers

(Winter Haven)Part-Time:Driver Opportunity

Winter Haven, FL

$3,500 - $6,000

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Winter Haven, FL

$3,136 - $5,600

Heavy Freight Logistics

Start ASAP:Cargo Van / Box Truck Specialist(Winter Haven)

Winter Haven, FL

$5,000 - $8,500

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Winter Haven, FL

$2,760 - $4,830

On-Demand Tasks Network

Hiring in Winter Haven:Driver Opportunity(Part-Time)

Winter Haven, FL

$2,000 - $4,000

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Winter Haven, FL

$3,000 - $5,500

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Winter Haven, FL

$3,219 - $5,520

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

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 50+ open driving jobs in Winter Haven, FL. They range from CDL-A truck driving and local home-daily routes to delivery, box truck, bus and non-CDL driving work. New routes are added daily.
How much do driving jobs pay in Winter Haven?
Pay in Winter Haven depends on the licence and the type of driving: delivery and non-CDL routes usually run $18–$26/hr, local CDL work $22–$32/hr, and CDL-A regional or OTR seats $1,200–$1,900 a week. Night runs and specialised freight such as flatbed or tanker pay more.
Are there driving jobs in Winter Haven with no experience?
Yes. Many employers in Winter Haven run paid CDL training or hire recent CDL school graduates, and non-CDL delivery, shuttle and rideshare work needs only a regular licence and a clean record.
Can I get a driving job in Winter Haven that is home every night?
Local routes in Winter Haven are home daily, including delivery, box truck, yard, dump truck and local CDL-A work. Regional runs get you home weekly, and OTR means longer stretches away for higher weekly pay.
Do I need a CDL to drive in Winter Haven?
Not for every job. Cargo van, sprinter, courier, shuttle and most 26' box truck routes need only a regular driver's licence. A CDL-B is needed for heavier straight trucks and buses, and a CDL-A for tractor-trailers.
What do employers check before hiring a driver in Winter Haven?
Your driving record for the last 3–5 years, a background check, and for commercial roles a DOT physical and drug test. Most insurers require drivers to be at least 21 for interstate work.
Which companies are hiring drivers immediately in Winter Haven?
Many carriers, delivery firms and local fleets in Winter Haven hire on a rolling basis, with start dates often within one to two weeks of applying. Browse the 50+ open routes above and apply directly.

Last updated: October 28, 2026