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.

Galveston Getaway
Enjoy our best available monthly rates all summer when you reserve any of our monthly luxury vacation rentals for June, July and August 2022. Historic Key West Vacation Rentals' monthly vacation rental properties are the perfect option for an extended stay in our tropical paradise...Read more
key west airport
Getting to Key West can be fun and magical. Making the drive from Miami to our southernmost point is among the most extraordinary, but the Conch Republic is happy to welcome guests from all over. Getting here is easier than ever and these are the...Read more
key west gramping with kids
Booking your Key West rental home is just the beginning! Historic Key West Vacation Rentals is here to help you plan your Key West vacation. Our little Key West island offers endless fun-filled activities and events such as water excursions, historical tours, fishing charters, and...Read more
Francie's Place
Francie's Place , our new Monthly Rental , invites you to be our guests. This luxury studio is perfect for singles or a couple and it has everything you need to enjoy your month’s stay in Key West. Unlike other studios, this one is adorned...Read more
dreaming on duval
I Love Stock Island Festival is June 15-19, 2022. This five-day festival is to feature one-of-a-kind Stock Island-inspired activities and authentic immersive experiences in the local Key West community, culture, and art. It's a great way to celebrate Father’s Day weekend with friends and family...Read more
key west pride
Key West Pride is June 1-5, 2022. Presented by the Key West Business Guild, events showcase the diversity and welcoming atmosphere that make the southernmost city a top vacation destination for LGBTQ visitors. The festival schedule typically includes pool parties at guesthouses and emporiums, drag...Read more
conch republic independence
Every year visitors join Florida Keys residents for the Conch Republic Independence Celebration , a quirky event honoring the birth of the republic and its place in Keys history. The republic was founded in April 1982 to protest the installation of a U.S. Border Patrol...Read more
dreaming on duval
Dreaming of Key West and a fantastic luxury vacation to the Caribbean? Dreams do come true in Key West! Be our guests in this private wonderland on the quieter end of Duval Street. Dreaming On Duval has added new high end decor and furnishings just...Read more
Key West 200th Anniversary
Join the multi-day 200th anniversary of Key West ’s first permanent settlement, commemorating the date of March 25, 1822, when U.S. Navy Lt. Matthew Perry planted the American flag on island soil, thereby solidified Key West's special place in history. Celebrate the island's history, architecture,...Read more
key west songwriters festival
May 4-8, 2022 is the 26th annual Key West Songwriters Festival in beautiful and historic Key West. It is one of the largest festivals of its kind in the world, and has grown into both a tourist attraction and favorite of island locals. The festival...Read more