Driving Jobs in Key West, FL — Immediate Openings

As of May 2026, there are 50+ open driving positions in Key West, FL. Current pay ranges from $14 to $145,800 per year. Top hiring areas include Delivery Driver, Cdl Driver and Yard Jockey. New roles are posted daily — listings on this page are verified and updated regularly.

Grubhub

Immediate Opening in Key West for a Suburban Delivery Driver | Hiring

Key West, FL

$3,360 - $5,488

DoorDash

Immediate Opening in Key West for a Flower Delivery Driver | Hiring

Key West, FL

$2,400 - $4,200

Foremost Transport

Key West-based Mobile Home Transport Driver-CDL A Oversize Load

Key West, FL

$90,000 - $120,000

Shipt

Shipt Needs Pharmacy Delivery Driver in Key West | Hiring

Key West, FL

$3,348 - $5,616

DoorDash

Join Doordash in Key West as a Morning Shift Delivery Driver | Hiring

Key West, FL

$2,970 - $5,060

First Student

First Student seeks School Bus Driver-CDL B With Passenger And S

Key West, FL

$18 - $25

Urban Pedal Logistics

Key West,FL:Independent Contractor Driver-Urban E-bike/scooter Courier

Key West, FL

$2,500 - $4,500

Regional Expedite Logistics

Work in Key West:Independent Contractor Driver-Long Distance /

Key West, FL

$3,500 - $6,000

Coach USA

Key West,FL:Charter Bus Driver-CDL B With Passenger Endorsement at

Key West, FL

$23 - $33

Secure Document Couriers

Key West Career:Independent Contractor Driver-Night Shift

Key West, FL

$2,800 - $5,000

Quest Diagnostics

Work in Key West:Delivery Driver-Medical Courier Pharmaceuticals

Key West, FL

$20 - $26

XPO Logistics

XPO Logistics Needs Delivery Driver-Package Handler Box Truck in Key

Key West, FL

$22 - $28

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 14, 2026