Driving Jobs in Winter Park, FL — See Openings

As of May 2026, there are 40+ open driving positions in Winter Park, FL. Current pay ranges from $14 to $143,000 per year. Top hiring areas include Delivery Driver, Cdl Driver and General. New roles are posted daily — listings on this page are verified and updated regularly.

Coach USA

Join Team in Winter Park:Charter Bus Driver-CDL B With Passenger

Winter Park, FL

$22 - $32

Postmates

Winter Park Contractor Same-day Delivery Driver | Hiring

Winter Park, FL

$2,944 - $4,968

Auto Logistics Pros

Independent Contractor Driver-Auto Parts Courier|Winter Park,FL|Auto

Winter Park, FL

$2,800 - $4,800

United Parcel Service (UPS)

United Parcel Service(UPS)Needs UPS Package Delivery Driver in Winter

Winter Park, FL

$4,000 - $7,500

DoorDash

Flower Delivery Driver Position in Winter Park | Hiring

Winter Park, FL

$2,112 - $3,696

XPO Logistics

Immediate Opening in Winter Park for a Delivery Driver-Package Handler

Winter Park, FL

$22 - $28

Foremost Transport

Recruiting in Winter Park:Mobile Home Transport Driver-CDL A Oversize

Winter Park, FL

$90,000 - $120,000

On-Demand Tasks Network

On-demand Tasks Network(Winter Park)Hiring:Independent Contractor

Winter Park, FL

$2,000 - $4,000

Urban Pedal Logistics

Winter Park,FL:Independent Contractor Driver-Urban E-bike/scooter

Winter Park, FL

$2,500 - $4,500

Secure Document Couriers

Independent Contractor Driver-Night Shift Legal/document

Winter Park, FL

$2,800 - $5,000

MTA New York City Transit

Winter Park Transit Bus Driver-CDL B Public Transportation with

Winter Park, FL

$33 - $46

Instacart

FL Career:Pet Supply Delivery Driver in Winter Park | Hiring

Winter Park, FL

$2,900 - $4,800

Driving Jobs in Winter Park — FAQ

How many driving jobs are available in Winter Park, FL right now?
There are currently 40+ 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 40+ listings above and apply directly.

Last updated: May 13, 2026