Driving Jobs in Winter Haven, FL — Start This Week

As of September 2026, there are 20+ open driving jobs in Winter Haven, FL. Current pay ranges from $14 to $90,000 per year. Top hiring areas include Delivery Driver and Box Truck. New roles are posted daily — listings on this page are verified and updated regularly.

Transportation Concepts

Part-Time Non-cdl Box Truck Delivery Driver(Winter Haven) | Part

Winter Haven, FL

$20 - $26

Performance Foodservice

Part-Time CDL Class A Route Delivery Driver(Winter

Winter Haven, FL

$70,000 - $90,000

Spark Driver

Part-Time Walmart Spark Delivery Driver(Winter Haven) | Part Time

Winter Haven, FL

$15 - $21

Domino's Pizza

Part-Time Job in Winter Haven – Delivery Driver | Part Time Job

Winter Haven, FL

$14 - $22

Quest Diagnostics

Student-Friendly Part-Time Medical Courier Delivery Driver in

Winter Haven, FL

$15 - $22

UPS

Part-Time Job in Winter Haven – Package Delivery Driver | Part

Winter Haven, FL

$23 - $30

DoorDash

Part-Time Role in Winter Haven:Delivery Driver-Dasher | Part Time

Winter Haven, FL

$15 - $25

Amazon Flex

Evening Part-Time Delivery Driver-Independent Contractor – Winter

Winter Haven, FL

$18 - $25

FedEx

Winter Haven Part-Time Job:Ground Delivery Driver | Part Time Job

Winter Haven, FL

$21 - $26

Amazon DSP

Part-Time Delivery Driver – Winter Haven FL | Part Time Job

Winter Haven, FL

$22 - $28

Domino's Pizza

Pizza Delivery Driver

Winter Haven, FL

$2,700 - $4,536

Amazon DSP

Amazon DSP Delivery Driver

Winter Haven, FL

$3,850 - $5,280

Driving Jobs in Winter Haven — FAQ

How many driving jobs are available in Winter Haven, FL right now?
There are currently 20+ 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 20+ open routes above and apply directly.

Last updated: September 28, 2026