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

As of May 2026, there are 28 delivery driver openings in Winter Park, FL. Local pay ranges from $14 to $118,800/year. Listings are updated daily — benefits start Day 1 for most positions.

Postmates

Winter Park Contractor Same-day Delivery Driver | Hiring

Winter Park, FL

$2,944 - $4,968

Auto Logistics Pros

Independent Contractor Driver-Auto Parts Courier|Winter Park,FL|Auto

Winter Park, FL

$2,800 - $4,800

United Parcel Service (UPS)

United Parcel Service(UPS)Needs UPS Package Delivery Driver in Winter

Winter Park, FL

$4,000 - $7,500

DoorDash

Flower Delivery Driver Position in Winter Park | Hiring

Winter Park, FL

$2,112 - $3,696

XPO Logistics

Immediate Opening in Winter Park for a Delivery Driver-Package Handler

Winter Park, FL

$22 - $28

Urban Pedal Logistics

Winter Park,FL:Independent Contractor Driver-Urban E-bike/scooter

Winter Park, FL

$2,500 - $4,500

Secure Document Couriers

Independent Contractor Driver-Night Shift Legal/document

Winter Park, FL

$2,800 - $5,000

Instacart

FL Career:Pet Supply Delivery Driver in Winter Park | Hiring

Winter Park, FL

$2,900 - $4,800

Instacart

Flexible Gig:Delivery Driver-Grocery Same Day Service(Winter Park)

Winter Park, FL

$16 - $23

DoorDash

Winter Park Morning Shift Delivery Driver with $2.8k-$4.8k/Month Pay

Winter Park, FL

$2,835 - $4,830

Local Merchant Delivery Network

$2.4k-$4.2k/Month Independent Contractor Driver-Early Morning

Winter Park, FL

$2,400 - $4,200

Roadie

Winter Park Big & Bulky Delivery Driver(Contractor)-Roadie | Hiring

Winter Park, FL

$4,830 - $8,280

Delivery Driver Jobs in Winter Park — FAQ

How many delivery driver jobs are open in Winter Park, FL?
There are currently 28+ delivery driver positions in Winter Park, FL. New delivery driver roles are added regularly — check this page for the latest openings.
How much do delivery driver jobs pay in Winter Park?
Delivery Driver pay in Winter Park 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 Park require experience?
Many delivery driver positions in Winter Park 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 Park?
Browse the 28+ 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 Park

Cdl Driver Jobs in Winter Park

9 open positions

Other Driving Jobs in Winter Park

2 open positions

Yard Jockey Jobs in Winter Park

1 open positions

Last updated: May 13, 2026