Key West Boat Rental – The best companies

by Paul Joseph  |  Published November 4, 2019

Perched within the Florida Keys archipelago, the island city of Key West is a mecca for yachting enthusiasts from across America and beyond, thanks to its stunning coral reefs and world class diving and snorkelling opportunities. On land, pastel-hued, conch style house add plenty of character and charm, while several buildings pay tribute to the many famous writers, including Ernest Hemingway, Robert Frost, and Tennessee Williams, who once called Key West home.

Two sailing yachts pictured against a Key West sunset (Photo: Mike NortonFollow via Flickr / CC BY 2.0)

For visitors seeking a yacht charter on Key West, there’s no shortage of options. To help you find the right rental agency for you preferences and needs, we’ve dug deep and picked out three charter companies located on and around the island, using a criteria including range of yachts available, company policies, and testimonials by previous customers.

Sailo claim to offer some 30,000 vessels of every kind for charter in destinations all over the world, with charters of just a few hours or up to a few weeks available. Users can conduct searches based on their favoured location, guest numbers, boat category, boat size, pricing and other pertinent criteria, and they can also speak directly with the boat operator via the website. When we searched for yacht charters on Key West, we found 17 vessels, including 8 sailboats and 6 catamarans, and in total 6 bareboat options are available, most offered with a captain, for 2, 4 or 8 hours. The cheapest yacht available during our search was a 30-foot catamaran starting at $350 per day.
Now into its sixth year, peer-to-peer website Boatsetter has swiftly become a big mover and shaker within South Florida’s yacht charter sector. The company brings charters, owners and licensed captains together, enabling them to connect with each other and arrange charter deals via the online platform. Users have the choice of requesting a booking through the website, or by messaging an owner directly to make enquiries about their vessel. As Boatsetter don’t directly operate or control the yachts on offer, they apply rigorous insurance policies to help protect both charters and owners, including requiring a minimum $500 security deposit for each rental. When we searched for yachts available on Key West, we found 28 options, including 5 sail boats and 3 bareboat vessels.
Boatbookings are one of the biggest and most renowned yacht charter companies operating in the market and they have a total of 6 yachts available for charter on Key West. Among their fleet are yachts ranging from 11 to 46-metres, 1 of which is offered as bareboat (no skipper or crew) and the rest as crewed yachts. Boatbookings also has 1 catamaran available for Key West charters, with cats being the most popular request from charterers in the region. The website also offers a comprehensive reviews section, giving visitors the chance to pore over the experiences of former guests who have used Boatbookings for charters.