Serving Osprey, Sarasota County
Trailer Rental in Osprey, FL
Osprey and Casey Key — a quick hop up US-41 to our yard. Our 16 and 20 foot enclosed car haulers move classics, sports cars, and bikes with everything out of the weather, and handle estate cleanouts and moves just as well.
Trailers Available Near Osprey, FL
Our Full Fleet
2024 8.5x20 Diamond Cargo Enclosed Trailer
Enclosed Trailer · 8.5 x 20 ft, 7 ft interior height
$165/day
2025 8.5x16 Hook & Line Cargo Enclosed Trailer
Enclosed Trailer · 8.5 x 16 ft, 7 ft interior height
$125/day
2024 8.5x16 Haulmark Transport Enclosed Trailer
Enclosed Trailer · 8.5 x 16 ft, 7 ft interior height
$125/day
How to Rent a Trailer from Osprey
Choose Online
Browse our fleet from Osprey. Filter by type, size, and price.
Book & Pay
Select your dates, upload insurance, and pay securely online.
Pick Up
Drive to our Sarasota (12 min). Directions come with your confirmation.
Return
Bring it back when you're done. Extensions available if needed.
Why Osprey Residents Choose Us
Upfront Pricing
Daily, weekly, and monthly pricing. Tax shown upfront at checkout.
Book Online in 60 Seconds
No phone tag. No paperwork. Choose your trailer, dates, and pay — done.
Self-Service Pickup
Lockbox code sent via text. Pick up and return 7AM-10PM.
Trusted by Locals
Real reviews from real customers across our service area.
Free Straps & Equipment
Every rental includes straps, ramps, and tools at no extra charge.
Locally Owned
We live and work right here in Sarasota. When you call, you talk to the owner.
Also Serving Nearby Areas
Ready to Rent a Trailer?
Browse our fleet and book online — it takes under 60 seconds.
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