About Vacation Key West


A letter from our CEO

I am pleased to welcome you to Vacation Key West!

In 1994, the company was started to offer Key West visitors answers to the questions they had. I realized that there simply were not many resources to make vacation planning a breeze for tourists. Therefore, Vacation Key West was born!

We 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.

Now, I am pleased to say that over the last 20 years, myself and the team have been collecting knowledge to become experts on Key West. We do live here, after all!

Key West is so very special to us, and we want to share it with you. Surrounded by the warm waters of the Caribbean, the chance to enjoy the ocean is enticing. We will answer all of your questions. Where should you stay? We have an answer for that. What should you do? Well, we have an answer for that too. What should you eat? Well, 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 McCaffrey, CEO of Vacation Key West


About us & our services

We are 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.

Contact myself or one of our knowledgable team members to help you plan your perfect stay so you don’t have to play the guessing game of where to go, what to do, where to stay, etc. We can handle all of your planning for you. My team and I are delighted to help you navigate this jewel of an island in the Keys!