Updated September 2026
Best Owner-Operator Companies in Hollywood, Florida (September 2026)
560 carriers are hiring owner-operators in Hollywood, Florida right now, per Lanefinder's September 2026 snapshot. RAY'S TRANSPORT INC leads with an average gross weekly revenue of $8,500 and an average $2,000 sign-on bonus. WINNERS TRANSPORTATION LLC follows at $2,657/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 September 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
How Hollywood, Florida compares to Florida
| Hollywood, Florida | Florida top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,679 | $5,326 | +25% |
| Dedicated routes | 43% | 35% | +8 pt |
| Riders-allowed policies | 92% | 84% | +8 pt |
| Pet-friendly fleets | 88% | 82% | +6 pt |
Source: Lanefinder index, September 2026
The largest gap is on average weekly pay: Hollywood, Florida sits 25% above the Florida baseline.
The owner-operator carriers leading Hollywood, Florida this month
The top of the list is RAY'S TRANSPORT INC at $8,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1RAY'S TRANSPORT INC — $8,500/wk
RAY'S TRANSPORT INC tops the Hollywood, Florida ranking with the strongest composite score across pay, safety, benefits, and operational signals. The carrier ranks in the 94th percentile for gross weekly revenue in Hollywood, Florida. Top FMCSA dimension here is driver fitness, in the 87th percentile. Application-response data flags this carrier as a responsive employer.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC ranks in the 92nd percentile for driver fitness on FMCSA SAFER data. Lanefinder's application data flags WINNERS TRANSPORTATION LLC as a responsive employer.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data. LOAD MONSTER INC responds to driver applications more reliably than the Hollywood, Florida median.
Also in the top 10: #4 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #5 WIDER GROUP INC at $6,250/wk, #6 Freight X LLC at $6,000/wk, #7 BLUE LIGHTNING LOGISTICS at $7,000/wk, #8 Ali Star Inc at $10,000/wk, #9 KILO METER LOGISTIC INC at $7,500/wk, #10 C & G TRANSPORTATION INC at $7,500/wk.
How drivers spend their time on the road in Hollywood, Florida
The route mix in Hollywood, Florida this month tilts OTR: 8% regional, 91% OTR, 0% local, 0% semi-local — drawn from active postings, not historical surveys.
Guaranteed pay is on offer at 2% of Hollywood, Florida postings; dedicated routes at 27%; take-truck-home at 91%. Pet-friendly policies appear at 72% and riders-allowed at 69%.
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 Hollywood, Florida
- CDL driver salary in Hollywood, Florida
- Best owner-operator companies in Florida
The methodology behind the rankings
Pay carriers in the same market against each other (30% of the score). Add a five-dimension FMCSA safety percentile from SAFER (25%). Score benefits based on whether the carrier hires W2 drivers or contractors (25%). Layer on employer responsiveness and fleet scale (20%). The weights are fixed and public. Updated September 2026.