Updated May 2026
Best Trucking Companies in Winter Garden, Florida (May 2026)
264 W2 trucking carriers are currently posting jobs in Winter Garden, Florida as of May 2026. 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.
Winter Garden, 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 leads the Winter Garden, Florida market on combined pay and ranking score this month. KEEP TRUCKING LLC pays above the 90th percentile on weekly pay for the Winter Garden, Florida market. On controlled-substances compliance, the carrier ranks in the 88th percentile per FMCSA SAFER data. KEEP TRUCKING LLC responds to driver applications more reliably than the Winter Garden, Florida median.
#2True Transport Inc. — $2,250/wk
True Transport Inc. sits in the 97th percentile for weekly pay among Winter Garden, Florida carriers. True Transport Inc.'s FMCSA score is strongest on unsafe-driving avoidance — 99th percentile. Driver applications get a faster-than-median response in Winter Garden, Florida.
True Transport Inc. doesn't top the ranking but offers higher weekly pay than #1 — $2,250/week.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC pays above the 90th percentile on weekly pay for the Winter Garden, Florida market. Strongest FMCSA dimension is unsafe-driving avoidance — 94th percentile.
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 Winter Garden, Florida
Of active CDL postings in Winter Garden, Florida this month, 17% are regional and 80% are OTR (long-haul). Local and semi-local routes account for the remaining 3%.
Across Winter Garden, Florida CDL postings: 2% with guaranteed pay, 28% dedicated, 82% take-truck-home, 62% pet-friendly, 66% riders-allowed.
Where Winter Garden, Florida differs from the Florida baseline
The largest gap is on dedicated routes: Winter Garden, Florida sits 10 points above the Florida baseline.
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 Winter Garden, Florida
- CDL driver salary in Winter Garden, Florida
- Best trucking companies in Florida
The methodology behind the rankings
Pay carriers against each other within the same market (30%). Layer a weighted FMCSA SAFER safety percentile on top (25%). Score the benefits package against what actually matters for the hiring type — W2 health/financial benefits or owner-op operational perks (25%). Finish with operational performance: responsiveness to driver applications plus fleet scale (20%). All percentiles are recomputed monthly. Updated May 2026.