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 Songwriters Festival
Key West Songwriters Festival is May 5-9, 2021 and Historic Key West Vacation Rentals has the finest collection of luxury boutique rentals that hit all the right notes. We'll sing in the sunshine and welcome songwriters from around the world to our Caribbean paradise. This...Read more
the pool at Starfish monthly rental
We're sharing 10 joys of spring in Key West. 2020 was not very joyful, so now it's time to travel, to laugh, to learn, to discover and to relax. Historic Key West Vacation Rentals' collection of luxury boutique vacation rentals welcome to you our Caribbean...Read more
chavez house pool
Sunny Key West is something to talk about, especially in winter. While the rest of the country is trudging through snow, sleet, rain, gray skies and quarantines, our Caribbean paradise is sharing the sunshine and good cheer. Our guests have lots of great things to...Read more
solaris cottage den
Solaris Cottage debuts new colors for spring and summer and you're invited to join in the celebration for Spring Break, Memorial Day, and summer vacations. Solaris Cottage is located on one of Key West’s most private slow lanes. This tranquil one-bedroom vacation rental was built...Read more
starfish cottage porch
Tucked away behind a gate, you'll find your slice of paradise in this hidden gem, Starfish. This spacious, bright two-bedroom, two-bath home, all on one level with a wrap-around porch for outdoor relaxation, is in the Southard Square community, which boasts a large shared pool...Read more
butterfly cottage decor
Butterly Cottage is our newest Key West nightly rental. This home has been totally "reborn" with new plumbing, central air conditioning, updated appliances in its brand new kitchen, and new flooring throughout the home. Televisions are in each bedroom and one in the main room...Read more
villa josine den
Here are 11 Key West places to soak up sunshine instead of shoveling lots of snow. We've all seen the weather reports and there's no denying winter is about to hit most of the country in a big way. For those who can't wait until...Read more
the pink house in key west
January 26 is National Plan For Vacation Day. What's so exciting about that? 54% of Americans are prioritizing exploring more of the United States with their time off in 2021! Yes, it's safe, exciting and productive to plan for the future and a visit to...Read more
cloud 9 pool
Your 13 best Key West vacation rentals for families are ready to welcome you from all around the country this spring. While we still need to be mindful of health and safety, there are lots to be said about the healing benefits of our warm...Read more
the Tiki Hut at Island Days
Plan ahead for 2021 Key West vacations and get your best sunshine-filled revenge on 2020! Last year was a year of canceled vacation plans, separations and lots of disappointments. This is the year when new vaccinations are ramping up and travelers are once again eager...Read more