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.

villa Josine pool
Will you summer by the pool or in the ocean when you vacation in Key West this year? Enjoy reading about more of our luxury boutique collection included in Part Two of this blog series. When you choose a luxury boutique vacation rental from the...Read more
cloud 9 decor
Historic Key West Vacation Rentals is sharing our amazing customer feedback so you'll know just what to expect when it's time for your visits! We take pride in our customer contact opportunities, correspondence with our guests, interactions and the feedback we receive. How do you...Read more
cloud 9 pool and outside dining
Will you summer by the pool or in the ocean when you vacation in Key West this year? When you choose a luxury boutique vacation rental from the Historic Key West Vacation Rentals collection you can do both. So many of our nightly , weekly...Read more
southern skies pool
Summer 2021 will bring lots of sunshine, tropical Caribbean breezes, exciting water adventures, fresh seafood, arts and music to our tropical paradise. Historic Key West Vacation Rentals is excited your summer vacations will bring you to Southern Skies of Key West, too! Southern Skies is...Read more
bohemian house pool
Historic Key West Vacation Rentals has 14 Key West spots available for the summer months. As temperatures rise this time of year, so does the fun and a month, or longer, by the sea is the best way to experience our Caribbean tropical paradise. Our...Read more
the new pool at Cloud 9
Cloud 9 is all-new for spring and Historic Key West Vacation Rentals invites you to experience the new decor. Just a half-block off Duval you’ll find this secret paradise awaiting you at Cloud 9. When you pass through the whimsical custom wrought iron gate decorated...Read more
key west southernmost point
Key West opens up for spring, summer, the arts, live shows and more and you're invited to come down to enjoy it all! Our tropical weather is cooperating just fine and our always beautiful Caribbean Sea is sending waves of welcome for repeat guests and...Read more
key west snorkeling
Key West is for snorkelers and now is the time to plan your summertime snorkeling adventures in the Caribbean. What better way to enjoy our Key West sunshine than to dive right in? Calm and incredibly flat water in the summer, 100-foot snorkel visibility at...Read more
Villa Luxe entrance
We've had our fill of staying home. We've tired of drive-through windows at our favorite restaurants that kept their doors locked. We've said so long to too many of our favorite spaces where we love to laugh, to talk, to eat, to share and to...Read more
Chick A Pea Cottage Bedroom
Positive guest experiences are what we're about. Key West is a magical, Caribbean paradise and it's the perfect setting for our collection of luxury boutique vacation rentals. We look forward to welcoming our guests and making their stays exceptional. We want you to know we...Read more