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Independent Contractor Driver Jobs in Key West, FL

Quiktrak

Field Inspector

Key West, FL · On-site

$25/hr

As an independent contractor, you will travel to assigned locations to perform floorplan audits ... Valid Driver's License (Required) United States Applicants Only

Quiktrak

Field Inspector

Key West, FL · Remote

$1.5K/mo

As an independent contractor, you will travel to assigned locations to perform floorplan audits ... Valid Driver's License (Required) United States Applicants Only

Quiktrakcontractor

Field Inspector

Key West, FL · On-site

$1.5K/mo

As an independent contractor, you will travel to assigned locations to perform floorplan audits ... Valid Driver's License (Required) United States Applicants Only

Quiktrakcontractor

Field Inspector

Key West, FL · On-site

$1.5K/mo

As an independent contractor, you will travel to assigned locations to perform floorplan audits ... Valid Driver's License (Required) United States Applicants Only

Quiktrak

Field Inspector

Key West, FL · On-site

$25/hr

As an independent contractor, you will travel to assigned locations to perform floorplan audits ... Valid Driver's License (Required) United States Applicants Only

Enterprise Holdings

Driver - Key West

Key West, FL

$15.50/hr

The Driver delivers vehicles and in some instances, customers, employees or vendors safely and ... independent regional subsidiaries. Enterprise Mobility and its affiliates offer extensive car ...

Enterprise Holdings

Driver - Key West

Key West, FL · On-site

$15.50/hr

The Driver delivers vehicles and in some instances, customers, employees or vendors safely and ... independent regional subsidiaries. Enterprise Mobility and its affiliates offer extensive car ...

Enterprise Holdings

Driver - Key West

Key West, FL · On-site

$15.50/hr

The Driver delivers vehicles and in some instances, customers, employees or vendors safely and ... independent regional subsidiaries. Enterprise Mobility and its affiliates offer extensive car ...

Temco Logistics

DFS Driver - Miami

Key West, FL · On-site

$23/hr

... independently. Our Delivery Drivers operate a 26 ft. box truck to deliver large and bulky items. A CDL is not required, and paid training is provided. Key Responsibilities: * Drive local home ...

Temco Logistics

DFS Driver - Miami

Key West, FL · On-site

$23/hr

... independently. Our Delivery Drivers operate a 26 ft. box truck to deliver large and bulky items. A CDL is not required, and paid training is provided. Key Responsibilities: * Drive local home ...

Navy Exchange

VENDING MECHANIC/ROUTE DRIVER

Key West, FL · On-site

$18.50 - $25/hr

VENDING MECHANIC/ROUTE DRIVER Location: United States-Florida-Key West Job Number: 260001Q4 Job ... As required accompanies Vending Contractors verifying case taken from vendor owned machines. Clears ...

Key West

VENDING MECHANIC/ROUTE DRIVER

Key West, FL · On-site

$24.38/hr

As required accompanies Vending Contractors verifying case taken from vendor owned machines. Clears ... JOB REQUIREMENTS 1. Must possess a valid state driver s license or a valid commercial driver s ...

US Foods, Inc.

Delivery Driver

Key West, FL · On-site

$30 - $36/hr

BECOME A US FOODS ® DRIVER! Ready to build a career with a company that's leading the foodservice industry? We help YOU make it! $33.88 for Key West Delivery Drivers Must reside and deliver in Key ...

Hampton Inn Key West

Van Driver

Key West, FL · On-site

$12.75 - $17.50/hr

We are pleased to announce a wonderful opportunity for a Van Driver. What will you be doing most days? * Provide safe dependable, reliable transportation guests of the hotel * Pick up and drop off ...

OTO Development

Van Driver

Key West, FL

$12.75 - $17.50/hr

We are pleased to announce a wonderful opportunity for a Van Driver. What will you be doing most days? * Provide safe dependable, reliable transportation guests of the hotel * Pick up and drop off ...

Hilton Worldwide Holdings

Van Driver

Key West, FL · On-site

$12.75 - $17.50/hr

We are pleased to announce a wonderful opportunity for a Van Driver. What will you be doing most days? * Provide safe dependable, reliable transportation guests of the hotel * Pick up and drop off ...

wm

CDL Commercial Driver

Key West, FL · On-site

Commercial Driver License (CDL) Class B with an air-brake endorsement B. Preferred Qualifications * High School Diploma or GED (accredited) IV. Physical Requirements Listed below are key points ...

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All JobsIndependent Contractor Driver JobsIndependent Contractor Driver Jobs in Key West, FL

Independent Contractor Driver information

See Key West, FL salary details

$389

$1.1K

$2.1K

How much do independent contractor driver jobs pay per week?

As of Aug 27, 2026, the average weekly pay for independent contractor driver in Key West, FL is $1,077.54, according to ZipRecruiter salary data. Most workers in this role earn between $713.46 and $1,198.08 per week, depending on experience, location, and employer.

What is an independent contractor driver?

Independent contractor drivers are self-employed individuals who provide driving services to businesses or customers without being classified as employees. They often work for ride-sharing companies, delivery services, or freight transport, using their own vehicles and setting their own schedules. As independent contractors, they are responsible for their own taxes, insurance, and vehicle maintenance, and they may work for multiple companies at once. This role offers flexibility, but also requires more personal responsibility and business management than a traditional employee position.

What does an independent contractor driver do?

An independent contractor driver may work in delivery or personal transportation. If you work in freight or goods transportation, your duties are to determine the simplest route to make your deliveries, load and unload your vehicle, and fill out paperwork on behalf of your employer and the organization receiving goods. In human transportation, independent contractor drivers contract with companies and operate their own vehicles for fares, such as working for rideshare services. Your responsibilities include maintaining your vehicle, purchasing insurance, and maintaining a good driver rating.

How do independent contractor drivers typically manage fluctuating workloads and income variability?

Independent Contractor Drivers often experience fluctuating workloads and income due to factors like seasonal demand, market trends, and client schedules. To manage this variability, many drivers diversify their client base, schedule work in advance when possible, and budget carefully to account for leaner periods. Building strong relationships with reliable clients and using load boards or delivery platforms can also help secure more consistent assignments. Additionally, maintaining a well-organized schedule and proactively seeking new opportunities are key strategies for sustaining steady work as an independent contractor.

What is the difference between Independent Contractor Driver vs Delivery Driver?

AspectIndependent Contractor DriverDelivery Driver
CredentialsDriver's license, vehicle insurance, possibly a commercial licenseDriver's license, vehicle insurance
Work EnvironmentSelf-employed, flexible schedule, operates own vehicleEmployed by a company, fixed routes or schedules, company vehicle often provided
Employer & Industry UsageWorks independently across various industries like ride-sharing or freightWorks for companies like food delivery, parcel services, or courier companies

Independent Contractor Drivers typically operate as self-employed individuals with flexible schedules and their own vehicles, serving multiple industries. Delivery Drivers are usually employed by companies, follow set routes, and may use company vehicles. Both roles require a valid driver's license and insurance, but their employment structure and work environment differ significantly.

Is being an independent contractor driver worth it?

Being an independent contractor driver offers flexibility in scheduling and the potential for higher earnings based on hours worked and efficiency. However, it also involves managing your own expenses, insurance, and taxes, with income variability depending on demand and market conditions.
More about Independent Contractor Driver jobs

What are the most commonly searched types of Driver jobs in Key West, FL?

The most popular types of Driver jobs in Key West, FL are:

What job categories do people searching Independent Contractor Driver jobs in Key West, FL look for?

The top searched job categories for Independent Contractor Driver jobs in Key West, FL are:

What cities near Key West, FL are hiring for Independent Contractor Driver jobs?

Cities near Key West, FL with the most Independent Contractor Driver job openings:

Independent Contractor Driver jobs near you
Infographic showing various Independent Contractor Driver job openings in Key West, FL as of August 2026, with employment types broken down into 1% As Needed, 67% Full Time, 29% Part Time, and 3% Contract. Highlights an 99% Physical, and 1% Remote job distribution, with an average salary of $56,032 per year, or $26.9 per hour.

Mortgage Field Inspector (1099 Independent Contractor)

GIS Field Services

Key West, FL • On-site

$20/hr

Full-time, Part-time, Contractor

Re-posted 8 days ago

Job description

Mortgage Field Inspector (1099 Independent Contractor)
Flexible Schedule | Part-Time or Full-Time | Weekly Pay
GIS Field Services, Inc. has been in the mortgage field inspection industry for over 20 years and is based out of Dallas, TX. Please visit our website to learn more about us and the industry. www.gisfieldservices.com.
We are seeking reliable and detail-oriented Independent Mortgage Field Inspectors to perform property inspections on behalf of mortgage companies. No licensing or certifications are required, and prior experience is a plus-but not necessary.
This is a great opportunity for self-motivated individuals who enjoy working independently, traveling locally, and managing their own schedule. Inspections may include exterior occupancy checks, and occasional interior vacant or damage inspections.
Job Title:Mortgage Occupancy Field Inspector County Coverage: Monroe
Your role as a Mortgage Field Inspector
  • Conduct property inspections for existing mortgage loans
  • Determine occupancy status (occupied or vacant)
  • Photograph and document property condition
  • Deliver door notices and verify utility status
  • Complete reports using a mobile app (InspectorADE)
  • Communicate regularly with the Inspection Relations Coordinator

What We Offer
  • Flexible schedule - work during daylight hours
  • Part-time or full-time based on your availability and territory
  • Flat rate per inspection (earning potential typically $20+/hour depending on volume)
  • Weekly pay via direct deposit
  • Work independently in your assigned territory

Requirements for the role
  • Valid driver's license
  • Reliable vehicle covered by auto insurance to travel within your territory.
  • Smartphone (iPhone or Android)
  • Computer with internet access
  • Printer and basic office supplies
  • Ability to obtain a Shield ID (Aspen Grove ABC#) If onboarding with GIS, we will provide you with the link to obtain your Shield ID
  • HUD/Inspector keys (set of 11) If onboarded with GIS, we will provide a link with a discount code to obtain your HUD/Inspector Keys
  • Volt stick
  • Strong time management, attention to detail, and communication skills

Important Details
  • This is a 1099 independent contractor position.
  • No mileage or expense reimbursement
  • Earnings depend on your availability, territory, and workload.
  • Must be comfortable inspecting occupied, vacant, and rural properties.

Apply