Updated July 2026
Best Owner-Operator Companies in Kissimmee, Florida (July 2026)
585 carriers in Kissimmee, Florida are actively recruiting owner-operators as of July 2026. Each is scored on a composite of compensation, FMCSA safety, benefits, and operational performance. ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $5,500. Performance Trucking Inc follows at $8,000/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 July 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 | $6,389 | $5,428 | +18% |
| Riders-allowed policies | 90% | 82% | +8 pt |
| Pet-friendly fleets | 84% | 78% | +6 pt |
Source: Lanefinder index, July 2026
The largest gap is on average weekly pay: Kissimmee, Florida sits 18% above the Florida baseline.
Kissimmee, Florida's top owner-operator carriers right now
The top of the list is ROLLING ON WHEELS LLC at $5,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1ROLLING ON WHEELS LLC — $5,500/wk
ROLLING ON WHEELS LLC leads the Kissimmee, Florida market on combined gross revenue and ranking score this month. ROLLING ON WHEELS LLC's FMCSA score is strongest on driver fitness — 96th percentile. Lanefinder's application data flags ROLLING ON WHEELS LLC as a responsive employer.
#2Performance Trucking Inc — $8,000/wk
Performance Trucking Inc sits in the 93rd percentile for gross weekly revenue among Kissimmee, Florida carriers.
#3WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data. Lanefinder's application data flags WINNERS TRANSPORTATION LLC as a responsive employer.
Also in the top 10: #4 INLAND EMPIRE LLC at $7,875/wk, #5 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #6 OVERLOG INC at $3,613/wk, #7 WIDER GROUP INC at $6,250/wk, #8 BLUE LIGHTNING LOGISTICS at $7,000/wk, #9 C & G TRANSPORTATION INC at $7,500/wk, #10 BB8 FREIGHT CO at $12,666/wk.
How drivers spend their time on the road in Kissimmee, Florida
Of active CDL postings in Kissimmee, Florida this month, 8% are regional and 91% are OTR (long-haul). Local and semi-local routes account for the remaining 1%.
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 July 2026.