High-paying driving jobs in Winter Haven
Driving involves operating vehicles to transport passengers or goods safely. Drivers must follow traffic laws and ensure the vehicle's maintenance. They need good reflexes, focus, and the ability to navigate roads efficiently, often in various weather conditions.
We found 716 high-paying for you in Winter Haven, FL. These driving jobs pay well, with salaries between $56,849 to $245,859 per hour. Popular roles include Truck Driver, Delivery Driver and Driver (independent Contractor).
Job title
Updated Oct 18, 2026
Job title
Winter Haven, FL
Florida
Job openings (Winter Haven)
Owner Operator Driver
Winter Haven
$4,498
per week
Florida
$5,443
per week
Truck Driver
Winter Haven
$2,398
per week
Florida
$2,344
per week
Commercial Driver
Winter Haven
$1,327
per week
Florida
$1,816
per week
Local Driver
Winter Haven
$1,230
per week
Florida
$1,077
per week
Driver (independent Contractor)
Winter Haven
$28.64
per hour
Florida
$30.46
per hour
Delivery Driver
Winter Haven
$20.36
per hour
Florida
$19.30
per hour
Driver
Winter Haven
$17.91
per hour
Florida
$19.51
per hour
Job descriptions below are for educational purposes. Please refer to the employer's job description for complete details.
-
Owner Operator Driver
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Please refer to the employers job description for complete details.
Owner Operator Drivers transport goods safely, manage logistics, and ensure compliance with regulations. Skills in route planning, knowledge of trucking regulations, and strong self-discipline are essential.
Owner Operator Driver jobs take 69 days on average from job posting to starting date. Currently, 2% of job openings are part-time roles.
See 21 jobsAverage pay
Winter Haven
$4,498 per weekFlorida
$5,443 per week -
Truck Driver
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Please refer to the employers job description for complete details.
Truck Drivers transport goods, maintain logs, and ensure vehicle safety. A valid commercial driver's license, adherence to regulations, and time management skills are essential. Experience in long-haul driving is advantageous.
Truck Driver jobs take 93 days on average from job posting to starting date. Currently, 2% of job openings are part-time roles.
See 295 jobsAverage pay
Winter Haven
$2,398 per weekFlorida
$2,344 per weekSkills
- Driving
- Load & unload
- Bus driving
- Commercial driving
-
Commercial Driver
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Please refer to the employers job description for complete details.
Commercial drivers operate various vehicles to transport goods or passengers, ensuring compliance with safety laws. A valid commercial driver's license and reliability are key qualifications for this role.
Commercial Driver jobs take 58 days on average from job posting to starting date. Currently, 53% of job openings are part-time roles.
See 9 jobsAverage pay
Winter Haven
$1,327 per weekFlorida
$1,816 per week -
Local Driver
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Please refer to the employers job description for complete details.
Local Drivers transport goods, ensure timely deliveries, and maintain vehicle condition. Knowledge of local routes, a clean driving record, and the ability to manage time effectively are essential.
Local Driver jobs take 68 days on average from job posting to starting date. Currently, 4% of job openings are part-time roles.
See 45 jobsAverage pay
Winter Haven
$1,230 per weekFlorida
$1,077 per weekSkills
- Load & unload
- Bus driving
- Driving
-
Driver (independent Contractor)
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Please refer to the employers job description for complete details.
Independent contractor drivers use their own vehicles for deliveries, managing their own schedules and client interactions. Strong self-management skills, reliable transportation and knowledge of local routes are essential in this role.
Driver (independent Contractor) jobs take 60 days on average from job posting to starting date. Currently, 92% of job openings are part-time roles.
See 101 jobsAverage pay
Winter Haven
$28.64 per hourFlorida
$30.46 per hour -
Delivery Driver
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Please refer to the employers job description for complete details.
Delivery Drivers transport goods safely, navigate routes efficiently, and manage timely deliveries. They need valid driving licenses, strong knowledge of navigation tools, and effective time management to meet schedule demands and ensure customer satisfaction.
Delivery Driver jobs take 171 days on average from job posting to starting date. Currently, 42% of job openings are part-time roles.
See 153 jobsAverage pay
Winter Haven
$20.36 per hourFlorida
$19.30 per hourSkills
- Driving
- Load & unload
- Bus driving
- Hindi
- English
-
Driver
Review job description
Please refer to the employers job description for complete details.
Drivers operate vehicles safely, follow schedules, and handle delivery documentation. A valid driver's license, time management skills, and navigation abilities are essential.
Driver jobs take 81 days on average from job posting to starting date. Currently, 47% of job openings are part-time roles.
See 92 jobsAverage pay
Winter Haven
$17.91 per hourFlorida
$19.51 per hourSkills
- Driving
- Load & unload
- Bus driving
- Automotive repair