Delivery Driver Jobs in Winter Haven, FL — Apply Today

As of May 2026, there are 170 delivery driver openings in Winter Haven, FL. Local pay ranges from $425 to $8,500/year. Listings are updated daily — benefits start Day 1 for most positions.

Heavy Haul Last Mile

Student-Friendly Part-Time Heavy/bulky Item Delivery Specialist

Winter Haven, FL

$3,344 - $4,840

Uber

Winter Haven Career:Connect Package Delivery Driver at Uber | Hiring

Winter Haven, FL

$3,000 - $5,500

Campus Courier Network

Weekend Shift:Driver Opportunity-Winter Haven

Winter Haven, FL

$2,730 - $5,040

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Winter Haven, FL

$3,080 - $5,500

Uber

Winter Haven Contractor Role:Ubereats Bicycle & Scooter Courier

Winter Haven, FL

$2,500 - $4,500

Corporate Transit Solutions

B2B Corporate Route Courier

Winter Haven, FL

$3,200 - $4,500

Instacart

Campus Area Instacart Delivery Driver

Winter Haven, FL

$2,808 - $5,184

Mechanic's Choice Transport

Automotive Parts Courier

Winter Haven, FL

$2,800 - $4,200

US Postal Service Contractors

Highway Contract Route (HCR) Driver

Winter Haven, FL

$3,520 - $6,160

Metro Pedal Express

Urban Bicycle Courier (Downtown Dispatch)

Winter Haven, FL

$2,500 - $4,000

Local Merchant Delivery Network

Now Hiring:Independent Contractor Driver-Early Morning Bakery/floral

Winter Haven, FL

$2,400 - $4,200

Local Merchant Delivery Network

Immediate Opening in Winter Haven for a Independent Contractor

Winter Haven, FL

$2,688 - $4,704

Delivery Driver Jobs in Winter Haven — FAQ

How many delivery driver jobs are open in Winter Haven, FL?
There are currently 170+ delivery driver positions in Winter Haven, FL. New delivery driver roles are added regularly — check this page for the latest openings.
How much do delivery driver jobs pay in Winter Haven?
Delivery Driver pay in Winter Haven varies by employer, route type, and experience level. Many positions offer shift differentials, mileage bonuses, and sign-on bonuses. Browse the listings above to see pay details for each opening.
Do delivery driver jobs in Winter Haven require experience?
Many delivery driver positions in Winter Haven welcome entry-level applicants. Employers like Amazon, FedEx, and UPS often provide paid training. CDL positions may require a valid commercial license — check individual listings for specific requirements.
How do I apply for delivery driver jobs in Winter Haven?
Browse the 170+ delivery driver listings above, click on any position for full details including pay, schedule, and requirements, then follow the application link. Most driving positions have a simple online application.

Delivery Driver Jobs in Other Cities

Delivery Driver Jobs in Springfield

844 open positions

Delivery Driver Jobs in Columbus

653 open positions

Delivery Driver Jobs in Columbia

603 open positions

Delivery Driver Jobs in Lakewood

603 open positions

Delivery Driver Jobs in Greenville

569 open positions

Delivery Driver Jobs in Bloomington

553 open positions

Delivery Driver Jobs in Auburn

531 open positions

Delivery Driver Jobs in Franklin

527 open positions

Delivery Driver Jobs in Albany

510 open positions

Delivery Driver Jobs in Middletown

494 open positions

Other Driving Jobs in Winter Haven

Other Driving Jobs in Winter Haven

13 open positions

Part-Time Driving Jobs in Winter Haven

6 open positions

Cdl Driver Jobs in Winter Haven

3 open positions

Grocery Jobs in Winter Haven

3 open positions

DSP Driver Jobs in Winter Haven

2 open positions

Weekend Driving Jobs in Winter Haven

1 open positions

Warehouse Jobs in Winter Haven

1 open positions

Overnight Driving Jobs in Winter Haven

1 open positions

Last updated: May 03, 2026