Delivery Driver Jobs in Winter Haven, FL — Open Positions

As of May 2026, there are 199 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.

Midnight Logistics

Earn Extra Cash:Late Night Convenience & Grocery Courier

Winter Haven, FL

$2,800 - $4,800

Grubhub

Suburban Route Grubhub Driver

Winter Haven, FL

$2,400 - $4,200

XPO Logistics

Flexible Local City Driver(Winter Haven)

Winter Haven, FL

$5,000 - $8,000

Uber

Winter Haven Contractor Night Shift Ubereats Courier | Hiring

Winter Haven, FL

$2,800 - $4,800

Paws In Motion Mobile

[Part-Time] Driver Opportunity-Winter Haven

Winter Haven, FL

$3,800 - $6,175

Uber

Work in Winter Haven:WAV Rideshare Driver | Hiring

Winter Haven, FL

$4,024 - $6,324

Uber

Part-time Ubereats Driver(lunch Rush)|Winter Haven,FL|Uber | Hiring

Winter Haven, FL

$800 - $1,800

Lyft

Event Rideshare Driver-Winter Haven,FL | Hiring

Winter Haven, FL

$2,800 - $5,000

Secure Legal Logistics

Legal & Secure Document Courier

Winter Haven, FL

$3,675 - $5,775

Instacart

Urban E-Bike Instacart Courier

Winter Haven, FL

$2,625 - $4,725

Final Mile Delivery Co.

Winter Haven,FL:Independent Contractor Driver-Final Mile Parcel at

Winter Haven, FL

$3,000 - $5,500

Uber

Weekend Rideshare Driver Position in Winter Haven | Hiring

Winter Haven, FL

$2,000 - $3,500

Delivery Driver Jobs in Winter Haven — FAQ

How many delivery driver jobs are open in Winter Haven, FL?
There are currently 199+ 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 199+ 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.

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Other Driving Jobs in Winter Haven

Other Driving Jobs in Winter Haven

13 open positions

Cdl Driver Jobs in Winter Haven

12 open positions

Part-Time Driving Jobs in Winter Haven

6 open positions

DSP Driver Jobs in Winter Haven

3 open positions

Grocery Jobs in Winter Haven

3 open positions

Warehouse Jobs in Winter Haven

2 open positions

Weekend Driving Jobs in Winter Haven

1 open positions

Overnight Driving Jobs in Winter Haven

1 open positions

Last updated: May 08, 2026