Delivery Driver Jobs in Winter Haven, FL — Start This Week

As of May 2026, there are 155 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

Winter Haven-based Uberx Driver Opening | Hiring

Winter Haven, FL

$3,000 - $5,000

US Postal Service Contractors

Highway Contract Route (HCR) Driver

Winter Haven, FL

$3,400 - $5,950

Uber

Ubereats Large Order Delivery Driver(Contract)-Winter Haven,FL

Winter Haven, FL

$3,500 - $6,000

On-Demand Tasks Network

Independent Contractor Driver - On-Demand Errands (TaskRabbit/Roadie)

Winter Haven, FL

$1,760 - $3,520

Lyft

Lyft seeks XL Rideshare Driver in Winter Haven | Hiring

Winter Haven, FL

$4,000 - $6,500

Lyft

FL Career:Event Rideshare Driver in Winter Haven | Hiring

Winter Haven, FL

$2,800 - $5,000

Local Shopper Partners

Courier needed in Winter Haven(Apply Now)

Winter Haven, FL

$2,000 - $3,500

Grubhub

Winter Haven Part-Time Job:Large Order Delivery Driver | Part

Winter Haven, FL

$3,500 - $6,000

Grubhub

Winter Haven Part-Time Job:Suburban Route Driver | Part Time Job

Winter Haven, FL

$2,400 - $4,200

United States Postal Service

Assistant Rural Carrier (Weekend & Holiday Delivery)

Winter Haven, FL

$1,724 - $2,875

Grubhub

Grubhub Large Order Delivery Driver

Winter Haven, FL

$4,024 - $6,899

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Winter Haven, FL

$3,136 - $5,600

Delivery Driver Jobs in Winter Haven — FAQ

How many delivery driver jobs are open in Winter Haven, FL?
There are currently 155+ 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 155+ 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

12 open positions

Part-Time Driving Jobs in Winter Haven

5 open positions

Cdl Driver Jobs in Winter Haven

3 open positions

Grocery Jobs in Winter Haven

2 open positions

Warehouse Jobs in Winter Haven

1 open positions

Weekend Driving Jobs in Winter Haven

1 open positions

DSP Driver Jobs in Winter Haven

1 open positions

Last updated: May 04, 2026