Key West Vacation Guide

Key West is a VERY dog-friendly town! Furry friends are even allowed in some bars and restaurants on our island. There are also several dog parks and even a dog beach! If you wish to travel with your dog(s), we do have dog-friendly vacation homes available.

Key West Directions Sign
Be your own best company for a much needed real vacation and head for America's Caribbean Islands. As a sun seeker, all you need to pack is tee shirts, shorts, flip flops, a swimsuit, a snorkel and mask, good hygiene and a face mask, and...Read more
sea vista pool deck
Welcome to the year of virtual classrooms. We know as parents some of you are coming to terms with the reality of remote learning for your children. How will you keep your children engaged while learning at home? What will your new normal look like?...Read more
solaris cottage bedroom
2020 will be remembered as the year of scaled-back celebrations, yet Key West is still a dream wedding destination for couples looking to get married, to elope, to have commitment ceremonies and for vow renewals. Getting a Florida marriage license is very easy. There is...Read more
the best thing about historic key west vacation rentals
We're sharing some of our favorite cottages, condos, townhouses, Conch homes, and compounds — and some of the very kind words from our guests who love them, too. Historic Key West Vacation Rentals is dedicated to the satisfaction of our homeowners, rental guests and our...Read more
key west vacation spots for social distancing
The coming school year will take place in virtual classrooms, which means you need a real vacation now . We all still need to follow Covid-19 safety guidelines — and that's no problem at Historic Key West Vacation Rentals. We have every type of vacation...Read more
quiet key west retreat
Make Yourself at Home at Casa Del Rio Tucked back on a quiet Key West street, Casa Del Rio is a spectacular four-bedroom, two-bathroom home. The property is centrally located to many great shops, restaurants, and attractions . Take a short walk down White Street...Read more
Dry Tortugas Fort Jefferson
Key West is famous for a lot of things that make it a favorite, family-friendly destination. Even now with travel challenges and virus guidelines in place, our Conch Republic is still a welcoming destination to kick back, relax and enjoy. Our warm sunny weather means...Read more
key west guests say it best
Our Historic Key West Vacation Rentals team takes great pride in preparing each property with your comfort and convenience in mind. We don't just make the beds. We're committed to making your stay exceptional and unforgettable. You can imagine the pride and sense of a...Read more
key west hemingway days
Ernest Hemingway first visited Key West on a trip from Paris. He said it felt like living in another country, so he moved in. He sport fished and sailed, refereed boxing matches and lived his life. He also wrote and left an impression that can...Read more
monthly vacation rentals in key west
Key West is a paradise of sun, fun, laid back living, the arts, food, the gulf and the ocean. How long should you visit to take it all in? Historic Key West Vacation Rentals recommends at least 28 days and even longer. Monthly vacation rentals...Read more