Used SUV that tows 5,000 lbs and fits a family under $30k?

For your budget and needs, the Honda Pilot is the safest pick. The Toyota Highlander has a serious reliability problem in the exact model years you would likely afford, and the Kia Telluride is mostly out of your price range. The Pilot gives you three rows for your family of five, tows up to 5,000 pounds, and has no major red flags in the owner data.

The Highlander looks tempting on price, with typical used examples ranging from about $18,600 to $29,600. But owner reports show a very frequent issue: the 8-speed automatic transmission fails on gas models from roughly 2017 to 2022. Repairs run around $7,000 or more. That failure pattern is too common to ignore, especially for a daily driver and road trip vehicle. Even if you find one under $30,000, the risk of a costly repair outweighs the savings.

The Honda Pilot has no reported issues in the owner data for the models you would consider. Used prices range from about $16,300 to $42,700, with a median around $23,000, so you have plenty of room to find a well-equipped example under $30,000. The Pilot seats up to eight, so five people fit easily, and its towing capacity covers your 5,000-pound trailer. No transmission or engine problems show up in the data, which makes it the most reliable choice for daily driving and long trips.

The Kia Telluride is a great SUV, but the price is the problem. Typical used prices start around $25,300 and go up to $35,200, with a median near $29,500. That means most examples are at or above your budget, leaving little room for taxes, fees, or a warranty. The owner data shows no major issues, but you would likely have to stretch your budget or settle for a base model with higher miles. If you can find one under $30,000, it is worth a look, but it is not the practical default.

Go with a Honda Pilot. Look for a 2019 or newer model with around 40,000 to 60,000 miles. Check the service history for regular maintenance, and confirm the towing package is included. That combination gives you the space, towing ability, and reliability you need without gambling on a known transmission failure.