Driving Jobs in Key West, FL — Open Positions

As of May 2026, there are 50+ open driving positions in Key West, FL. Current pay ranges from $560 to $8,500 per year. Top hiring areas include Delivery Driver, General and Grocery. New roles are posted daily — listings on this page are verified and updated regularly.

Uber

Uber Needs Ubereats Delivery Driver in Key West | Hiring

Key West, FL

$2,500 - $4,500

Healthway Logistics

Independent Medical Specimen Courier

Key West, FL

$3,150 - $5,250

On-Demand Tasks Network

On-demand Tasks Network(Key West)Hiring:Independent Contractor

Key West, FL

$2,000 - $4,000

United Parcel Service (UPS)

FL Career:UPS Package Delivery Driver in Key West | Hiring

Key West, FL

$4,000 - $7,500

Uber

Uber seeks Airport Driver in Key West | Hiring

Key West, FL

$3,500 - $5,500

Heavy Freight Logistics

Key West Career:Independent Contractor Driver-Cargo Van / Box Truck

Key West, FL

$5,000 - $8,500

Secure Document Couriers

Join Secure Document Couriers in Key West as a Independent Contractor

Key West, FL

$3,136 - $5,600

Local Logistics Network

Independent Contractor Driver-Medical Courier|Key West,FL|Local

Key West, FL

$3,449 - $5,750

Uber

Key West Job:Part-time Ubereats Driver(lunch Rush)(Contractor)

Key West, FL

$800 - $1,800

Urban Pedal Logistics

Independent Contractor Driver-Urban E-bike/scooter Courier(Gig Economy

Key West, FL

$2,125 - $3,825

Secure Document Couriers

Recruiting:Independent Contractor Driver-Night Shift Legal/document

Key West, FL

$2,800 - $5,000

Uber

$2.7k-$4.5k/Month Uberx Driver job in Key West | Hiring

Key West, FL

$2,730 - $4,550

Driving Jobs in Key West — FAQ

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

Last updated: May 03, 2026