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.

chick a pea front porch
When you've been dreaming of your Key West getaway, you'll be glad you chose one of these four luxury vacation rentals just steps from Duval Street. Location is key when you want to experience our Floribbean flavors of fresh seafood and fine cuisine, the arts,...Read more
cloud 9 pool
While most are still dealing with colder weather, Key West is more than delighted to invite you to shovel sunshine. Spring in Key West is truly paradise. It's our delightful heat and wonderful sunshine that create this twist that defies colder temperatures everywhere else. These...Read more
Fernwood Monthly Rental
Our four most luxurious Key West Snowbird Vacation Rentals for 2023 are fully furnished premier homes that are perfect for long-term month stays in Key West , winter vacations and remote working assignments. In fact, our luxury Key West vacation rentals vacation planners are dedicated...Read more
key west christmas tree
Happy Holidays to you! Historic Key West Vacation Rentals is proud to announce seven opportunities for seasonal savings in December 2022. We've lowered the rates of all of our remaining Key West monthly rentals through the end of the year. Key West's mild weather means...Read more
potters cottage pool dining
Come and dine. It's turkey time! The holidays are all about spending quality time with family and friends and Historic Key West Vacation Rentals wants to help take some of the stress out of entertaining. Why worry about whose home should host your holiday gatherings...Read more
Bahari House Work Remote Office
Work remotely in Key West and live like a local while doing your best at your dream job. No commute. No lunch rush. No travel costs. Save time for a better life filled with adventures that will make you a better employee. You'll have better...Read more
fantasy fest
Enjoy our new fall savings for Fantasy Fest October 21-30, 2022. We've lowered the nightly rates for our remaining luxury vacation rentals and we invite you to be our guests this festival season. Cult Classics and Cartoon Chaos is the theme for this year's 10-day...Read more
magical margaret
Introducing Magical Margaret, the newest Key West monthly rental to join our luxury vacation rentals collection. It's available for your fall and winter vacations beginning November 2022. As you enter the main home you will be captivated by the high-end kitchen, natural light, and hardwood...Read more
miss sunshine parking
A virtual tour of Miss Sunshine is just the glimpse of one of the best places to stay on your Key West Vaction . Historic Key West Vacation Rentals' Key West Monthly Rentals are the perfect option for an extended stay in our tropical paradise...Read more
Miss Sunshine Monthly Rental
The seven best Snowbird luxury rentals in Key West are available through Historic Key West Vacations Rentals. They're the best because they're located in this tropical paradise surrounded by crystal blue waters separated from the high octane speed of life on the mainland. All laid...Read more

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