Delivery Driver Jobs in Winter Garden, FL — Apply Today

As of May 2026, there are 151 delivery driver openings in Winter Garden, FL. Local pay ranges from $500 to $9,520/year. Listings are updated daily — benefits start Day 1 for most positions.

Final Mile Delivery Co.

Winter Garden Job:Independent Contractor Driver-Final Mile Parcel

Winter Garden, FL

$3,000 - $5,500

FedEx

Fedex seeks Delivery Driver in Winter Garden | Hiring

Winter Garden, FL

$4,024 - $7,474

Shipt

Urgent Hire in Winter Garden:Courier

Winter Garden, FL

$2,000 - $3,500

Uber

Weekend Rideshare Driver Position in Winter Garden | Hiring

Winter Garden, FL

$2,000 - $3,500

Uber

Winter Garden-based Uberx Driver Opening | Hiring

Winter Garden, FL

$3,000 - $5,000

Corporate Catering Couriers

Join Corporate Catering Couriers in Winter Garden as a Independent

Winter Garden, FL

$3,500 - $6,000

Grubhub

Part-Time Job in Winter Garden – Campus Area Driver | Part Time

Winter Garden, FL

$2,600 - $4,800

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Winter Garden, FL

$2,520 - $4,410

DoorDash

DoorDash Drive (B2B/Merchant) Delivery Courier

Winter Garden, FL

$3,150 - $5,775

Uber

Night Shift Rideshare Driver•Winter Garden,FL•Uber | Hiring

Winter Garden, FL

$3,200 - $5,500

Corporate Catering Couriers

Independent Contractor Driver-Catering Logistics•Winter

Winter Garden, FL

$3,500 - $6,000

PepsiCo

Flexible Route Sales Delivery Driver(Winter Garden)

Winter Garden, FL

$4,500 - $7,000

Delivery Driver Jobs in Winter Garden — FAQ

How many delivery driver jobs are open in Winter Garden, FL?
There are currently 151+ delivery driver positions in Winter Garden, FL. New delivery driver roles are added regularly — check this page for the latest openings.
How much do delivery driver jobs pay in Winter Garden?
Delivery Driver pay in Winter Garden 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 Garden require experience?
Many delivery driver positions in Winter Garden 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 Garden?
Browse the 151+ 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 Garden

Other Driving Jobs in Winter Garden

14 open positions

Part-Time Driving Jobs in Winter Garden

6 open positions

Cdl Driver Jobs in Winter Garden

3 open positions

Grocery Jobs in Winter Garden

2 open positions

Weekend Driving Jobs in Winter Garden

2 open positions

Warehouse Jobs in Winter Garden

1 open positions

DSP Driver Jobs in Winter Garden

1 open positions

Last updated: May 04, 2026