Driving Jobs in Winter Park, FL — Apply Today

As of March 2026, there are 30+ open driving positions in Winter Park, FL. Current pay ranges from $500 to $7,500 per year. Top hiring areas include Delivery Driver and General. New roles are posted daily — listings on this page are verified and updated regularly.

Grubhub

Early Morning Grubhub Driver

Winter Park, FL

$1,870 - $3,230

Grubhub

Campus Area Grubhub Driver

Winter Park, FL

$2,600 - $4,800

Grubhub

Part-Time Grubhub Driver (Lunch Rush)

Winter Park, FL

$800 - $1,800

Grubhub

Suburban Route Grubhub Driver

Winter Park, FL

$2,208 - $3,864

Grubhub

Grubhub Bicycle & Scooter Courier

Winter Park, FL

$2,625 - $4,725

Grubhub

Night Shift Grubhub Courier

Winter Park, FL

$2,380 - $4,080

Grubhub

Grubhub Shop and Pay Driver

Winter Park, FL

$2,548 - $4,368

Grubhub

Weekend Grubhub Delivery Professional

Winter Park, FL

$2,200 - $3,800

Grubhub

Grubhub Large Order Delivery Driver

Winter Park, FL

$2,975 - $5,100

Grubhub

Grubhub Delivery Driver

Winter Park, FL

$2,875 - $5,175

Uber

Join Team:Connect Package Delivery Driver(Flexible,Winter Park)

Winter Park, FL

$2,730 - $5,005

Uber

Campus Area Ubereats Driver(Gig)-Winter Park

Winter Park, FL

$2,912 - $5,376

Driving Jobs in Winter Park — FAQ

How many driving jobs are available in Winter Park, FL right now?
There are currently 30+ 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 30+ listings above and apply directly.

Last updated: March 13, 2026