Driving Jobs in Winter Haven, FL — Hiring Now

As of October 2026, there are 21+ open driving jobs in Winter Haven, FL. Current pay ranges from $30 to $382,200 per year. Top hiring areas include Delivery Driver, Cdl A and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Nightline Freight

Winter Haven Part-Time Job:Overnight Parcel Transfer Driver

Winter Haven, FL

$3,600 - $5,200

Peak Season Logistics

Part-Time Job Winter Haven at Peak Season Logistics | Part Time

Winter Haven, FL

$3,675 - $5,250

Metro Parcel Delivery

Part-Time Urban Step Van Courier|Winter Haven,FL | Part Time Job

Winter Haven, FL

$3,230 - $4,675

Health Transit Logistics

Part-Time Medical & Pharmacy Package Courier at Health Transit

Winter Haven, FL

$3,360 - $4,725

Weekend Transit Co.

Part-Time Weekend Parcel Delivery Driver(Winter Haven) | Part

Winter Haven, FL

$1,320 - $2,200

Corporate Courier Logistics

Evening Part-Time B2B Route Logistics Driver – Winter Haven

Winter Haven, FL

$2,720 - $4,080

Heavy Haul Last Mile

Part-Time Heavy/bulky Item Delivery Specialist – Winter Haven FL

Winter Haven, FL

$3,344 - $4,840

E-Comm Transit Solutions

Part-Time E-commerce Delivery Specialist Job in Winter Haven

Winter Haven, FL

$3,360 - $5,040

Flex Delivery Network

Part-Time Independent Parcel Courier at Flex Delivery Network –

Winter Haven, FL

$2,000 - $4,000

Local Logistics Pros

Immediate Part-Time Local Package Delivery Driver Job – Winter

Winter Haven, FL

$3,300 - $4,950

Instacart

Winter Haven Job:Pet Supply Delivery Driver(Contractor) | Hiring

Winter Haven, FL

$2,900 - $4,800

Schneider National

CDL A Truck Driver - OTR Dry Van

Winter Haven, FL

$75,000 - $96,000

Driving Jobs in Winter Haven — FAQ

How many driving jobs are available in Winter Haven, FL right now?
There are currently 21+ 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 21+ open routes above and apply directly.

Last updated: October 05, 2026