Delivery Driver Jobs in Winter Haven, FL — Apply Today

As of March 2026, there are 126 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.

DoorDash

DoorDash Large Order (Catering) Driver

Winter Haven, FL

$3,850 - $6,600

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Winter Haven, FL

$3,360 - $6,160

Uber

Airport Driver(Gig Economy And Transportation)Vacancy in Winter Haven

Winter Haven, FL

$3,675 - $5,775

Urban Pedal Logistics

[Fresh] Courier-Winter Haven(PT)

Winter Haven, FL

$2,500 - $4,500

Shipt

Student Friendly:Driver Opportunity(Winter Haven)

Winter Haven, FL

$2,500 - $4,500

Uber

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

Winter Haven, FL

$3,500 - $5,500

Uber

Ubereats Delivery Driver•Winter Haven,FL•Uber | Hiring

Winter Haven, FL

$2,500 - $4,500

Uber

Suburban Route Ubereats Driver(Contract)-Winter Haven,FL

Winter Haven, FL

$2,040 - $3,570

Grubhub

Grubhub Shop and Pay Driver

Winter Haven, FL

$2,800 - $4,800

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Winter Haven, FL

$3,500 - $6,000

Grubhub

Grubhub Large Order Delivery Driver

Winter Haven, FL

$3,500 - $6,000

DoorDash

DoorDash Delivery Driver (Dasher)

Winter Haven, FL

$2,125 - $3,825

Delivery Driver Jobs in Winter Haven — FAQ

How many delivery driver jobs are open in Winter Haven, FL?
There are currently 126+ 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 126+ 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

Part-Time Driving Jobs in Winter Haven

4 open positions

Weekend Driving Jobs in Winter Haven

1 open positions

Grocery Jobs in Winter Haven

1 open positions

Warehouse Jobs in Winter Haven

1 open positions

Overnight Driving Jobs in Winter Haven

1 open positions

Cdl Driver Jobs in Winter Haven

1 open positions

Last updated: March 23, 2026