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.

Petite Maison - Key West Vacation Rental
Historic Key West Vacation Rentals is thrilled to participate in the first annual Vacation Rental Week — the first of its kind for the vacation and holiday rental industry! We’d like to use this opportunity to highlight the value and key benefits of professionally-managed vacation...Read more
Cruiser Bikes
When to visit Key West? Every time your spirit needs to be renewed, refreshed, revived and any time you need to fly your quirky flag. Apri is a wonderful time for all these to happen and we've even put together our agenda of fantastic events...Read more
Sunset Sailboat Cruise
Springtime is a great time to visit Key West. The sun is shining, fresh seafood arrives daily, celebrations and special events are lining up and the quirky quotient skyrockets. Pack light and head out for paradise. We've paired up some of the best special event...Read more
book direct with historic key west vacation rentals
#BookDirect Guest Education Day Is February 3, 2021! Book direct through Historic Key West Vacation Rentals and save on your Florida vacations. You'll always get our best available rates, access to our special offers, the most up-to-date information about our collection of premier vacation rentals,...Read more
family friendly home in key west
Welcome to Grand Maison , one of the best family-friendly homes in Key West. It's located in the Gallery District right on Duval Street and near the Southernmost Point. It's also just a few blocks away from several popular areas and a quick walk to...Read more
Woman lounging in pool in Key West
Hello, girls. You want to give it a go? Whether you're up for a progressive road trip or flying in for a few days, the southernmost point of our United States is the place for girls who want to have sun! There's lots to be...Read more
Key West Handmade Souvenirs
The best places in Key West to bring home souvenirs are as convenient as any street you like to stroll. Key West living is a culture and a way of life you must experience first hand. Five-toed cats and roving roosters aside, you're just as...Read more
new years at casa del rio in key west
New Years holidays are for saying goodbye to the old and welcoming in the new. In Key West, you'll have several great celebrations to enjoy and to do just that. When you visit you'll already be at the southernmost point in our country, so come...Read more
1105 Petronia Christmas
It's beginning to look a lot like Christmas in Key West! Take a look at these upcoming holiday events in Key West and then search for the perfect vacation rental.Read more
Key West Beach and Palm Trees
Our Key West beaches are just like the people who live here: exotic, sometimes quirky, and always fun. Here are our most favorite places to greet the seas.Read more

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