Updated May 2026
Best Trucking Companies in Kissimmee, Florida (May 2026)
Through May 2026, 263 carriers in Kissimmee, Florida employ W2 company drivers across the lanes Lanefinder tracks. KEEP TRUCKING LLC leads with an average weekly pay of $2,200. True Transport Inc. follows at $2,250/week. 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's top trucking carriers right now
The top of the list is KEEP TRUCKING LLC at $2,200/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1KEEP TRUCKING LLC — $2,200/wk
KEEP TRUCKING LLC is number-one in Kissimmee, Florida this month on the composite ranking. KEEP TRUCKING LLC pays above the 90th percentile on weekly pay for the Kissimmee, Florida market. KEEP TRUCKING LLC's top FMCSA dimension is controlled-substances compliance, in the 88th percentile. KEEP TRUCKING LLC responds to driver applications more reliably than the Kissimmee, Florida median.
#2True Transport Inc. — $2,250/wk
True Transport Inc.'s weekly pay ranks in the 97th percentile across Kissimmee, Florida. True Transport Inc.'s FMCSA score is strongest on unsafe-driving avoidance — 99th percentile. True Transport Inc. responds to driver applications more reliably than the Kissimmee, Florida median.
True Transport Inc. actually pays more weekly than the top-ranked carrier — $2,250/week.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC pays above the 90th percentile on weekly pay for the Kissimmee, Florida market. JK MOVING & STORAGE INC ranks in the 94th percentile for unsafe-driving avoidance on FMCSA SAFER data.
Also in the top 10: #4 Covenant Transport Inc at $1,762/wk, #5 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #6 KOTTKE TRUCKING INC at $2,000/wk, #7 Diaz Stone & Pallet Inc. at $1,750/wk, #8 DIVINE ENTERPRISES at $1,375/wk, #9 G-DIAMOND TRANSPORT INC at $2,045/wk, #10 ELBERTA LOGISTICS INTERNATIONAL LLC at $2,000/wk.
How drivers spend their time on the road in Kissimmee, Florida
17% of Kissimmee, Florida's active CDL postings are regional and 79% are OTR; local plus semi-local accounts for the rest (4%).
Across Kissimmee, Florida CDL postings: 2% with guaranteed pay, 28% dedicated, 81% take-truck-home, 62% pet-friendly, 65% riders-allowed.
How Kissimmee, Florida compares to Florida
| Kissimmee, Florida | Florida top 50 | Delta | |
|---|---|---|---|
| Dedicated routes | 41% | 29% | +12 pt |
| Pet-friendly fleets | 71% | 76% | -5 pt |
Source: Lanefinder index, May 2026
Among the figures above, dedicated routes is where Kissimmee, Florida differs most from Florida — 12 points above statewide.
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 owner-operator companies in Kissimmee, Florida
- CDL driver salary in Kissimmee, Florida
- Best trucking companies in Florida
Where this data comes from
Compensation is the largest single weight at 30% — pay percentile, sign-on bonus, guaranteed-pay availability, and settlement cadence. FMCSA safety contributes 25%, built from five SAFER dimensions with unsafe-driving and hours-of-service weighted 2× heavier. Benefits contribute 25%, scored separately for W2 versus owner-operator and 1099 carriers. Operational performance — application responsiveness and fleet scale — contributes 20%. Updated May 2026.