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Weekend Owner Operator Jobs in Florida (NOW HIRING)

Deep South Freight

CDL A Owner Operator

Panama City, FL · On-site

Maybe it's a dedicated route where you are home every day or home every weekend. Maybe it's owning your own truck. Maybe you're a driver who wants to stretch their legs and see the country. Whatever ...

Deep South Freight

CDL A Owner Operator

Crestview, FL · On-site

Maybe it's a dedicated route where you are home every day or home every weekend. Maybe it's owning your own truck. Maybe you're a driver who wants to stretch their legs and see the country. Whatever ...

Deep South Freight

CDL A Owner Operator

Orange Park, FL · On-site

Maybe it's a dedicated route where you are home every day or home every weekend. Maybe it's owning your own truck. Maybe you're a driver who wants to stretch their legs and see the country. Whatever ...

Deep South Freight

CDL A Owner Operator

Callahan, FL · On-site

Maybe it's a dedicated route where you are home every day or home every weekend. Maybe it's owning your own truck. Maybe you're a driver who wants to stretch their legs and see the country. Whatever ...

Deep South Freight

CDL A Owner Operator

Milton, FL · On-site

Maybe it's a dedicated route where you are home every day or home every weekend. Maybe it's owning your own truck. Maybe you're a driver who wants to stretch their legs and see the country. Whatever ...

Deep South Freight

CDL A Owner Operator

Pensacola, FL · On-site

Maybe it's a dedicated route where you are home every day or home every weekend. Maybe it's owning your own truck. Maybe you're a driver who wants to stretch their legs and see the country. Whatever ...

Deep South Freight

CDL A Owner Operator

Lawtey, FL · On-site

Maybe it's a dedicated route where you are home every day or home every weekend. Maybe it's owning your own truck. Maybe you're a driver who wants to stretch their legs and see the country. Whatever ...

Deep South Freight

CDL A Owner Operator

Grand Ridge, FL · On-site

Maybe it's a dedicated route where you are home every day or home every weekend. Maybe it's owning your own truck. Maybe you're a driver who wants to stretch their legs and see the country. Whatever ...

Deep South Freight

CDL A Owner Operator

Ebro, FL

Maybe it's a dedicated route where you are home every day or home every weekend. Maybe it's owning your own truck. Maybe you're a driver who wants to stretch their legs and see the country. Whatever ...

Deep South Freight

CDL A Owner Operator

Interlachen, FL · On-site

Maybe it's a dedicated route where you are home every day or home every weekend. Maybe it's owning your own truck. Maybe you're a driver who wants to stretch their legs and see the country. Whatever ...

Deep South Freight

CDL A Owner Operator

Vernon, FL

Maybe it's a dedicated route where you are home every day or home every weekend. Maybe it's owning your own truck. Maybe you're a driver who wants to stretch their legs and see the country. Whatever ...

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Weekend Owner Operator information

What are common challenges faced by weekend owner operators, and how can they be managed?

Weekend Owner Operators often encounter challenges such as tight delivery schedules, limited access to support services during off-hours, and balancing personal time with work commitments. To manage these effectively, it's important to plan routes in advance, maintain strong communication with dispatchers and clients, and ensure your vehicle is well-maintained to minimize unexpected issues. Building a reliable network of contacts and staying organized can also help mitigate stress and ensure smooth operations during weekend shifts.

What skills and qualifications are needed to thrive as a weekend owner operator?

To thrive as a Weekend Owner Operator, you need a valid commercial driver's license (CDL), a clean driving record, and strong knowledge of transportation regulations. Familiarity with logistics software, GPS navigation systems, and electronic logging devices (ELDs) is typically required. Strong time management, self-motivation, and communication skills help you manage deliveries and coordinate with dispatchers or clients. These competencies ensure on-time deliveries, compliance with safety standards, and the successful management of your independent business.

What is a weekend owner operator?

A Weekend Owner Operator is a self-employed truck driver who owns or leases their own commercial vehicle and typically works on weekends transporting goods. They contract with companies or brokers to haul freight, often having flexibility to choose their loads and work schedule. This role appeals to drivers seeking supplemental income or a work-life balance that accommodates weekday commitments. Weekend Owner Operators are responsible for managing their business expenses, maintenance, and compliance with transportation regulations.

What is the difference between Weekend Owner Operator vs Part-Time Delivery Driver?

AspectWeekend Owner OperatorPart-Time Delivery Driver
CredentialsCommercial driver's license (CDL) often required, vehicle insuranceValid driver's license, sometimes a background check
Work EnvironmentOwns and operates their vehicle, flexible schedule, independentWorks for a company, scheduled shifts, company vehicle often provided
Employer & IndustryIndependent contractor in freight or logisticsEmployee or contractor in delivery services

Weekend Owner Operators typically own their vehicle and operate independently, often in freight or logistics, with more flexibility. Part-Time Delivery Drivers usually work for a company, with scheduled shifts and less operational responsibility. Both roles involve driving, but the ownership and independence level differ significantly.

What are the most commonly searched types of Owner Operator jobs in Florida? The most popular types of Owner Operator jobs in Florida are:
What cities in Florida are hiring for Weekend Owner Operator jobs? Cities in Florida with the most Weekend Owner Operator job openings:
Weekend Owner Operator jobs near you
Infographic showing various Weekend Owner Operator job openings in Florida as of July 2026, with employment types broken down into 58% Full Time, and 42% Part Time. Highlights an 92% In-person, and 8% Remote job distribution.

Owner Operator CDL A Home Weekends

Assurity Transportation Solutions

Ocala, FL • On-site

$7.0K - $11K/wk

Full-time

Re-posted 14 days ago

Job description

Apply Now
Home weekends or stay out and run longer, totally up to you
7-11K weekly avg and up to 14K weekly
90% True Revenue to the Owner Operator
10% fuel discount
Plate and insurance program for those who need it
Be your own Boss and have the freedom you deserve along with the pay you deserve..
No Forced Dispatch
Dedicated Customer accounts, contract freight, general freight, drop and hook options, and much more
Run the areas you like to run or choose from dedicated lanes as available
Weekly settlements direct deposit
Use your trailer or ours Dry Van or Reefer
Sap OK
APPLY NOW for an Amazing year
The sky's the limit!
CDL A Owner Operator Positions with great pay and home time for work/life balance. We value you and your family. Trucking is a family decision. We are currently looking for experienced candidates who can meet these qualifications:
  • CDL A Owner Operator
  • All truck ages will be considered (good condition)
  • Valid CDL Class A
  • Current DOT Medical card
  • No DUI/DWI in past 7 years
  • Must have good work ethics

90% TRUE gross to you and home daily 7-11K weekly avg
  • 90% gross to you 10% fuel discount Gross $7,000-$11,000 on average weekly so if you are above average you will make even more $$$$$$$$ some drivers make up to 14k weekly.( Question is, how much do you want?
  • Can choose from Dedicated Lanes
  • Optional ..Access to self dispatch
  • Experienced assigned Fleet manager for your success
  • We have 2020 or newer Dry Vans /Dry general freight
  • Can Pre-book loads
  • No forced dispatch

Apply