Driving Jobs in Key West, FL — See Openings

As of April 2026, there are 30+ open driving positions in Key West, FL. Current pay ranges from $680 to $8,500 per year. Most openings are in Delivery Driver. New roles are posted daily — listings on this page are verified and updated regularly.

Wholesale Transit Partners

Evening Role:Driver Opportunity(Key West)

Key West, FL

$3,040 - $5,225

Local Shopper Partners

Key West Needs:Courier(Part-Time)

Key West, FL

$2,100 - $3,675

Grubhub

Weekend Grubhub Delivery Professional

Key West, FL

$2,200 - $3,800

Suburban Delivery Network

Evening Role:Driver Opportunity(Key West)

Key West, FL

$2,800 - $4,800

United Parcel Service (UPS)

UPS Package Delivery Driver Needed-Key West Area | Hiring

Key West, FL

$4,000 - $7,500

Urban Pedal Logistics

Urban Pedal Logistics seeks Independent Contractor Driver-Urban

Key West, FL

$2,500 - $4,500

On-Demand Tasks Network

Independent Contractor Driver-On-demand Errands|Key West,FL|On-demand

Key West, FL

$2,000 - $4,000

Final Mile Delivery Co.

Independent Contractor Driver-Final Mile Parcel|Key West,FL|Final Mile

Key West, FL

$3,000 - $5,500

Grubhub

Campus Area Grubhub Driver

Key West, FL

$2,730 - $5,040

Grubhub

Grubhub Bicycle & Scooter Courier

Key West, FL

$2,625 - $4,725

Grubhub

Grubhub Shop and Pay Driver

Key West, FL

$3,219 - $5,520

FreshDrop Logistics

$49.00/hr Driver Opportunity-Key West(PT)

Key West, FL

$3,000 - $5,500

Driving Jobs in Key West — FAQ

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

Last updated: April 26, 2026