Driving Jobs in Oldsmar, FL — Start This Week

As of April 2026, there are 30+ open driving positions in Oldsmar, FL. Current pay ranges from $728 to $8,500 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

Suburban Route Grubhub Driver

Oldsmar, FL

$2,520 - $4,410

United Parcel Service (UPS)

Oldsmar UPS Package Delivery Driver(Full-time)-United Parcel Service

Oldsmar, FL

$4,000 - $7,500

Grubhub

Grubhub Bicycle & Scooter Courier

Oldsmar, FL

$2,500 - $4,500

Grubhub

Grubhub Shop and Pay Driver

Oldsmar, FL

$3,024 - $5,184

Campus Courier Network

Student Friendly:Driver Opportunity(Oldsmar)

Oldsmar, FL

$2,470 - $4,560

FreshDrop Logistics

Flexible Hours:Driver Opportunity-Oldsmar

Oldsmar, FL

$3,000 - $5,500

Auto Logistics Pros

Oldsmar Job:Independent Contractor Driver-Auto Parts Courier

Oldsmar, FL

$2,800 - $4,800

Grubhub

Campus Area Grubhub Driver

Oldsmar, FL

$2,730 - $5,040

Grubhub

Grubhub Large Order Delivery Driver

Oldsmar, FL

$2,975 - $5,100

Urban Pedal Logistics

Oldsmar Job:Courier(No Exp Req*)

Oldsmar, FL

$2,500 - $4,500

Secure Document Couriers

Independent Contractor Driver-Night Shift Legal/document

Oldsmar, FL

$2,800 - $5,000

Urban Pedal Logistics

Join Urban Pedal Logistics in Oldsmar as a Independent Contractor

Oldsmar, FL

$2,500 - $4,500

Driving Jobs in Oldsmar — FAQ

How many driving jobs are available in Oldsmar, FL right now?
There are currently 30+ open driving positions in Oldsmar, 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 Oldsmar?
Driving job pay in Oldsmar 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 Oldsmar?
Yes. Many delivery driver, courier, and DSP positions in Oldsmar 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 Oldsmar?
Driving jobs in Oldsmar 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 Oldsmar?
Benefits vary by employer, but many driving positions in Oldsmar 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 Oldsmar?
Your take-home pay as a driver in Oldsmar 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 Oldsmar?
Yes, many driving positions in Oldsmar 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: April 26, 2026