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.

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 Spring Break vacation rentals for families are ready to welcome you from all around the country. Last year's spring getaways got delayed or canceled and 2021 is the year to take it all back. Let's call it your Revenge Spring...Read more
cloud 9 pool
Your best Key West Spring Break vacation rentals are ready to welcome you from all around the country. Last year's spring getaways got delayed or canceled and 2021 is the year to take it all back. Let's call it your Revenge Spring Break ! While...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
villa josine bedroom
Here are four Key West places for Valentine's Day. Cupid gets an extra day to sling arrows of love this year as President's Day falls on February 15. Take advantage of the long, romantic weekend and our best available rates. It's the perfect opportunity for...Read more
the den at Southard Comfort
Working 9 to 5 is the reality most of us deal with as part of our journey through life. If we want to cover our basic needs, provide for our families, and plan for the future most of us have to be on the clock...Read more
Chavez House pool
Here are 12 places Key West is serving up the sunshine. You'll feel right at home among our locals and our other winter Snowbirds. One thing we all have in common is our love for our warm, Caribbean lifestyle, our delicious fresh seafood, the arts,...Read more
poolside at inn cogneato
17 Cheers for Key West and 2021. 2020 may not have been the year we all wanted, but it was a year when our Historic Key West Vacation Rentals team rose above all the challenges and still delivered world-class service to our guests. We're thankful...Read more
john truman cottage waterfall
All the single ladies put your hands up if you're ready for a glorious, warm winter getaway to Key West! With the warmest winter weather and lots of sunshine to go around, who wouldn't want to visit, work, learn and play in our Caribbean paradise?...Read more
poolside at Cayo Limon
Choose from these five Key West vacation rentals for your 2021 winter getaways. Who wants to shovel snow when you can open up windows, doors and sometimes entire walls to let the sunshine in. Should you spend winter inside or outside? Winter in Key West...Read more

Pages