Driving Jobs in Winter Park, FL — Now Hiring

As of May 2026, there are 50+ open driving positions in Winter Park, FL. Current pay ranges from $500 to $8,500 per year. Top hiring areas include Delivery Driver, General and Warehouse. New roles are posted daily — listings on this page are verified and updated regularly.

Uber

Immediate Opening in Winter Park for a Uberx Driver | Hiring

Winter Park, FL

$2,640 - $4,400

Auto Logistics Pros

Join Auto Logistics Pros in Winter Park as a Independent Contractor

Winter Park, FL

$2,380 - $4,080

Heavy Route Couriers

Dedicated Route Freight Courier (Cargo Van)

Winter Park, FL

$4,000 - $6,000

Healthway Logistics

Independent Medical Specimen Courier

Winter Park, FL

$3,000 - $5,000

Uber

Apply Now:Campus Area Ubereats Driver in Winter Park | Hiring

Winter Park, FL

$2,600 - $4,800

Secure Legal Logistics

Legal & Secure Document Courier

Winter Park, FL

$3,675 - $5,775

United Parcel Service (UPS)

UPS Package Delivery Driver(Logistics And Transportation)Vacancy in

Winter Park, FL

$4,000 - $7,500

Secure Document Couriers

Winter Park Independent Contractor Driver-Night Shift Legal/document

Winter Park, FL

$2,800 - $5,000

Uber

Night Shift Ubereats Courier Position in Winter Park | Hiring

Winter Park, FL

$2,800 - $4,800

Auto Logistics Pros

Auto Logistics Pros Needs Independent Contractor Driver-Auto Parts

Winter Park, FL

$2,800 - $4,800

Uber

Immediate Opening in Winter Park for a Ubereats Shop And Pay Expert

Winter Park, FL

$2,800 - $4,800

Uber

Flexible Ubereats Bicycle & Scooter Courier in Winter Park,FL

Winter Park, FL

$2,500 - $4,500

Driving Jobs in Winter Park — FAQ

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

Last updated: May 03, 2026