Updated May 2026
Best Owner-Operator Companies in Kissimmee, Florida (May 2026)
590 carriers in Kissimmee, Florida are actively recruiting owner-operators as of May 2026. Each is scored on a composite of compensation, FMCSA safety, benefits, and operational performance. YANKEE FREIGHT SYSTEMS LLC leads with an average gross weekly revenue of $5,491 and an average $2,000 sign-on bonus. Zmile Inc follows at $2,987/week gross. Florida trucking runs on I-95 / I-75 north-south spines and the I-4 Tampa-Orlando-Daytona cross, with Port of Miami and Port of Jacksonville as major gateways alongside heavy citrus and produce agriculture freight.
What changed in May 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Kissimmee, Florida vs Florida: the numbers that diverge
| Kissimmee, Florida | Florida top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $7,027 | $5,580 | +26% |
| Riders-allowed policies | 90% | 79% | +11 pt |
| Pet-friendly fleets | 88% | 81% | +7 pt |
| Dedicated routes | 46% | 40% | +6 pt |
Source: Lanefinder index, May 2026
The largest gap is on average weekly pay: Kissimmee, Florida sits 26% above the Florida baseline.
Kissimmee, Florida's top owner-operator carriers right now
The top of the list is YANKEE FREIGHT SYSTEMS LLC at $5,491/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1YANKEE FREIGHT SYSTEMS LLC — $5,491/wk
YANKEE FREIGHT SYSTEMS LLC leads the Kissimmee, Florida market on combined gross revenue and ranking score this month. Strongest FMCSA dimension is hours-of-service compliance — 98th percentile. Application-response data flags this carrier as a responsive employer.
#2Zmile Inc — $2,987/wk
Zmile Inc ranks in the 98th percentile for hours-of-service compliance on FMCSA SAFER data. Zmile Inc responds to driver applications more reliably than the Kissimmee, Florida median.
#3Performance Trucking Inc — $8,000/wk
Performance Trucking Inc sits in the 93rd percentile for gross weekly revenue among Kissimmee, Florida carriers. Performance Trucking Inc's FMCSA score is strongest on driver fitness — 99th percentile.
Also in the top 10: #4 AD EXPRESS TRUCKING LLC at $2,525/wk, #5 WIDER GROUP INC at $6,250/wk, #6 D-LINE TRUCKING INC at $5,750/wk, #7 INLAND EMPIRE LLC at $7,875/wk, #8 Ali Star Inc at $10,000/wk, #9 BLUE LIGHTNING LOGISTICS at $7,000/wk, #10 Freight X LLC at $6,000/wk.
How drivers spend their time on the road in Kissimmee, Florida
Of active CDL postings in Kissimmee, Florida this month, 9% are regional and 89% are OTR (long-haul). Local and semi-local routes account for the remaining 2%.
Guaranteed pay is on offer at 2% of Kissimmee, Florida postings; dedicated routes at 27%; take-truck-home at 91%. Pet-friendly policies appear at 73% and riders-allowed at 68%.
Driving CDL in Florida
Florida CDL work splits cleanly between coastal port-and-tourism freight (Miami, Jacksonville, Tampa, Port Everglades) and Central Florida last-mile distribution. The hurricane season — June through November — drives both stress and opportunity: insurance rates climb, freight rates spike around storm-recovery windows, and shutdown days are a real income variable. Florida has no state income tax. The traffic on I-95 and I-4 is consistently in the top tier of US congestion, so HOS planning around peak commute windows matters more here than in most states. Reefer and produce work pays well; OTR pulling out of the state is steady year-round.
Related guides
- Best trucking companies in Kissimmee, Florida
- CDL driver salary in Kissimmee, Florida
- Best owner-operator companies in Florida
Where this data comes from
Carriers are scored against carriers in their own market. The composite is 30% compensation (pay + bonus + guaranteed pay + settlement cadence), 25% FMCSA safety, 25% benefits (W2 vs owner-op scoring), and 20% operational performance (responsiveness + fleet scale). No paid placement — the weights are the same for every carrier in the index. Updated May 2026.