Driving Jobs in Key West, FL — See Openings

As of September 2026, there are 20+ open driving positions in Key West, FL. Current pay ranges from $1,200 to $8,500 per year. Top hiring areas include Delivery Driver and Dsp. New roles are posted daily — listings on this page are verified and updated regularly.

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Key West, FL

$3,220 - $5,520

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Key West, FL

$2,500 - $4,500

On-Demand Tasks Network

Independent Contractor Driver - On-Demand Errands (TaskRabbit/Roadie)

Key West, FL

$1,700 - $3,400

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Key West, FL

$5,000 - $8,500

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Key West, FL

$2,576 - $4,600

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Key West, FL

$2,400 - $4,200

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Key West, FL

$3,675 - $6,300

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Key West, FL

$3,000 - $5,500

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Key West, FL

$2,380 - $4,080

United Parcel Service (UPS)

UPS Package Delivery Driver

Key West, FL

$4,400 - $8,250

Domino's Pizza

$2.5k-$4.2k/Month Pizza Delivery Driver job in Key West | Hiring

Key West, FL

$2,500 - $4,200

Amazon DSP

Key West Delivery Driver($4k-$5.5k/Month) | Hiring

Key West, FL

$4,024 - $5,520

Driving Jobs in Key West — FAQ

How many driving jobs are available in Key West, FL right now?
There are currently 20+ open driving positions in Key West, 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 Key West?
Driving job pay in Key West 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 Key West?
Yes. Many delivery driver, courier, and DSP positions in Key West 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 Key West?
Driving jobs in Key West 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 Key West?
Benefits vary by employer, but many driving positions in Key West 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 Key West?
Your take-home pay as a driver in Key West 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 Key West?
Yes, many driving positions in Key West 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: September 11, 2026