Driving Jobs in Winter Park, FL — Hiring Now

As of May 2026, there are 20+ open driving positions in Winter Park, FL. Current pay ranges from $14 to $85,000 per year. Top hiring areas include Delivery Driver and Cdl Driver. New roles are posted daily — listings on this page are verified and updated regularly.

Grubhub

Winter Park-based Suburban Delivery Driver Opening | Hiring

Winter Park, FL

$3,360 - $5,488

Instacart

Pet Supply Delivery Driver Position in Winter Park | Hiring

Winter Park, FL

$3,248 - $5,376

Quest Diagnostics

Quest Diagnostics seeks Delivery Driver-Medical Courier

Winter Park, FL

$20 - $26

DoorDash

Flower Delivery Driver Position in Winter Park | Hiring

Winter Park, FL

$2,520 - $4,410

Uber Eats

Alcohol Delivery Driver Needed-Winter Park Area | Hiring

Winter Park, FL

$2,550 - $4,250

GoPuff

FL Career:Convenience Store Delivery Driver in Winter Park | Hiring

Winter Park, FL

$2,800 - $4,500

Amazon Flex

Winter Park Job:Holiday Peak Delivery Driver(Contractor) | Hiring

Winter Park, FL

$5,175 - $8,625

Roadie

Winter Park-based Big & Bulky Delivery Driver Opening | Hiring

Winter Park, FL

$3,822 - $6,552

XPO Logistics

Winter Park,FL:Delivery Driver-Package Handler Box Truck at XPO

Winter Park, FL

$22 - $28

DoorDash

Work in Winter Park:Morning Shift Delivery Driver | Hiring

Winter Park, FL

$2,700 - $4,600

Shipt

Pharmacy Delivery Driver Position in Winter Park | Hiring

Winter Park, FL

$3,255 - $5,460

Express Logistics

Winter Park Career:Delivery Driver-Full Time Local Routes at Express

Winter Park, FL

$19 - $24

Driving Jobs in Winter Park — FAQ

How many driving jobs are available in Winter Park, FL right now?
There are currently 20+ open driving positions in Winter Park, 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 Park?
Driving job pay in Winter Park 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 Park?
Yes. Many delivery driver, courier, and DSP positions in Winter Park 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 Park?
Driving jobs in Winter Park 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 Park?
Benefits vary by employer, but many driving positions in Winter Park 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 Park?
Your take-home pay as a driver in Winter Park 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 Park?
Yes, many driving positions in Winter Park 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 20+ listings above and apply directly.

Last updated: May 10, 2026