About Us

Vanessa McCaffrey - Founder and Owner

Vanessa McCaffrey – Founder and Owner

Vacation Key West was created by Vanessa McCaffrey to accommodate the needs of visitors to the Florida Keys and Key West. The company, started in 1994, quickly grew from offering a handful of hotels, to providing expert advice on a myriad of lodging options in the Keys, including B&B’s, condos, guesthouses and vacation rentals. We once hired the tent that Oprah used to celebrate Maya Angelou’s birthday for a wedding on Sunset Key, it was a blast!

Vacation Key West is conveniently located in the Key West Ferry Terminal at 100 Grinnell Street in the Seaport area. We offer ferry packages that include roundtrip ferry tickets and accommodations in Key West, at bargain prices; these packages are very popular. Our team is profoundly knowledgeable and can find the best deals available for your stay. Frommers Guide recommends Vacation Key West when searching for lodging, and they say we are “skilled at finding last minute deals”. As experts we will give you priceless advice – at no charge to you.

Key West offers fishing, para-sailing, snorkeling, dinner cruises, sunset sailing, diving and many other activities on the water. Vacation Key West’s Tour Desk Department team knows the activities options like no one else on the island.

Call Us To Book Your Trip To The Dry Tortugas

Surrounded by the warm waters of the Caribbean, the chance to enjoy the ocean is enticing. Ask us for suggestions on where to eat, Key West has more gourmet chef’s in a square mile than anywhere else! In fact, whatever your desire, we can help you plan your stay so you don’t have to search through the maze of options. Vanessa and her team are delighted to help you navigate this jewel of an island in the Keys! Come Visit us at the Key West Ferry Terminal

Vacation Key West

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Vacation Key West 24.562538, -81.798994