Driving Jobs in Winter Haven, FL — Hiring Now

As of May 2026, there are 50+ open driving positions in Winter Haven, FL. Current pay ranges from $14 to $90,000 per year. Top hiring areas include Delivery Driver, Cdl Driver and Dsp. New roles are posted daily — listings on this page are verified and updated regularly.

FedEx Ground

Apply Today in Winter Haven:Delivery Driver-Package Handler | Hiring

Winter Haven, FL

$21 - $26

Domino's Pizza

Winter Haven Career:Delivery Driver-Pizza Delivery Tips Plus Wages at

Winter Haven, FL

$14 - $20

Wayfair

Winter Haven:Delivery Driver-Furniture And Appliance Home Installation

Winter Haven, FL

$21 - $27

Quest Diagnostics

Winter Haven Full-time Delivery Driver-Medical Courier Pharmaceuticals

Winter Haven, FL

$20 - $26

XPO Logistics

Winter Haven Flexible Job:Delivery Driver-Package Handler Box Truck

Winter Haven, FL

$22 - $28

Instacart

Join Instacart in Winter Haven as a Delivery Driver-Grocery Same Day

Winter Haven, FL

$16 - $23

Schneider National

Winter Haven-based Delivery Driver-CDL Class A Regional Routes Opening

Winter Haven, FL

$70,000 - $85,000

DoorDash

Flexible Gig:Delivery Driver-Food Delivery Part Time Evenings

Winter Haven, FL

$15 - $22

Amazon Flex

Winter Haven Delivery Driver-Independent Contractor(Contractor)-Amazon

Winter Haven, FL

$18 - $25

Express Logistics

Delivery Driver-Full Time Local Routes Needed-Winter Haven Area

Winter Haven, FL

$19 - $24

Roadie

Box Truck Delivery Driver

Winter Haven, FL

$4,095 - $7,098

Uber Eats

Daily Pay Delivery Driver

Winter Haven, FL

$3,136 - $5,376

Driving Jobs in Winter Haven — FAQ

How many driving jobs are available in Winter Haven, FL right now?
There are currently 50+ 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 50+ listings above and apply directly.

Last updated: May 10, 2026