Delivery Driver Jobs in Winter Haven, FL — See Openings

As of April 2026, there are 189 delivery driver openings in Winter Haven, FL. Local pay ranges from $500 to $8,500/year. Listings are updated daily — benefits start Day 1 for most positions.

Uber

Ubereats Bicycle & Scooter Courier(Gig)-Winter Haven

Winter Haven, FL

$2,500 - $4,500

FedEx Ground Independent Contractor

Weekend Shift:Driver Opportunity-Winter Haven

Winter Haven, FL

$3,800 - $5,700

Local Merchant Delivery Network

Work in Winter Haven:Independent Contractor Driver-Early Morning

Winter Haven, FL

$2,640 - $4,620

FedEx

Immediate Opening in Winter Haven for a Delivery Driver | Hiring

Winter Haven, FL

$4,024 - $7,474

Grubhub

Winter Haven Part-Time:Part-time Driver(lunch Rush)(Apply Now)

Winter Haven, FL

$800 - $1,800

Secure Document Couriers

Night Shift Legal/document Courier Needed-Winter Haven Area | Hiring

Winter Haven, FL

$2,800 - $5,000

Uber

Winter Haven WAV Rideshare Driver with $3.5k-$5.5k/Month Pay | Hiring

Winter Haven, FL

$3,500 - $5,500

US Postal Service Contractors

Highway Contract Route (HCR) Driver

Winter Haven, FL

$4,400 - $7,700

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Winter Haven, FL

$2,380 - $4,080

Uber

EV Rideshare Driver-Winter Haven,FL | Hiring

Winter Haven, FL

$3,000 - $5,500

Instacart

Late Night Instacart Courier

Winter Haven, FL

$2,940 - $5,040

Uber

Now Hiring:Night Shift Ubereats Courier(Flexible,Winter Haven)

Winter Haven, FL

$2,800 - $4,800

Delivery Driver Jobs in Winter Haven — FAQ

How many delivery driver jobs are open in Winter Haven, FL?
There are currently 189+ 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 189+ 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

15 open positions

Cdl Driver Jobs in Winter Haven

12 open positions

Part-Time Driving Jobs in Winter Haven

7 open positions

DSP Driver Jobs in Winter Haven

3 open positions

Grocery Jobs in Winter Haven

1 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: April 17, 2026