Driving Jobs in Winter Haven, FL — Apply Today

As of May 2026, there are 180+ open driving positions in Winter Haven, FL. Current pay ranges from $500 to $10,000 per year. Top hiring areas include Delivery Driver, General and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Uber

Winter Haven-based Uberx Driver Opening | Hiring

Winter Haven, FL

$3,000 - $5,000

US Postal Service Contractors

Highway Contract Route (HCR) Driver

Winter Haven, FL

$3,400 - $5,950

Uber

Ubereats Large Order Delivery Driver(Contract)-Winter Haven,FL

Winter Haven, FL

$3,500 - $6,000

On-Demand Tasks Network

Independent Contractor Driver - On-Demand Errands (TaskRabbit/Roadie)

Winter Haven, FL

$1,760 - $3,520

DoorDash

DoorDash Shop & Deliver Expert (Grocery/Retail)

Winter Haven, FL

$2,380 - $4,080

Lyft

Lyft seeks XL Rideshare Driver in Winter Haven | Hiring

Winter Haven, FL

$4,000 - $6,500

Lyft

FL Career:Event Rideshare Driver in Winter Haven | Hiring

Winter Haven, FL

$2,800 - $5,000

Local Shopper Partners

Courier needed in Winter Haven(Apply Now)

Winter Haven, FL

$2,000 - $3,500

Grubhub

Winter Haven Part-Time Job:Large Order Delivery Driver | Part

Winter Haven, FL

$3,500 - $6,000

Grubhub

Winter Haven Part-Time Job:Suburban Route Driver | Part Time Job

Winter Haven, FL

$2,400 - $4,200

United States Postal Service

Assistant Rural Carrier (Weekend & Holiday Delivery)

Winter Haven, FL

$1,724 - $2,875

Grubhub

Grubhub Large Order Delivery Driver

Winter Haven, FL

$4,024 - $6,899

Driving Jobs in Winter Haven — FAQ

How many driving jobs are available in Winter Haven, FL right now?
There are currently 180+ 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 180+ listings above and apply directly.

Last updated: May 04, 2026