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.

Sea Vista pool
The southernmost party for women and their friends is in Key West, presented by the Key West Business Guild. WomenFest has a simple goal: to celebrate ALL women! Key West WomenFest offers a wide range of activities for those who want to socialize, feel comfortable...Read more
villa josine rain porch
Here are nine Key West Rain Porches to add to your list of life's unexpected luxuries. A rain porch is an awning-like extension of the roof itself that dips down at an angle to shield the house from wind and rain. Most often, they feature...Read more
cloud 9 pool
End your summer in Key West with a big splash. Our collection of luxury boutique vacation rentals includes everything from intimate cottages and condos to larger, conch-style homes with indulgent outdoor rooms, pools and water features. When you're looking for an island escape with a...Read more
Starfish Monthly Rental in Key West
Here are 10 monthly stays where you can remote work, learn and play in Key West. Historic Key West Vacation Rentals has put together a collection of Caribbean cottages, condos, townhomes and Conch homes for those who prefer to work and learn outside of a...Read more
copa cabana
Our Key West guests recommend these monthly summertime cottages and Caribbean vacation rentals for your end-of-summer getaways. Historic Vacation Rentals has the premier collection of luxury boutique cottages, condos, townhomes, and conch-style houses. We're always happy to help you choose the best long term or...Read more
fish camp monthly rental
Seafood lovers can chow down on Florida’s clawless lobster during this tasty “feast-ival” that features a savory schedule of events ranging from a traditional lobster boil to a lively street fair starring the sensational crustacean prepared in a variety of ways. The flavorful festivities celebrate...Read more
cloud 9 den
Historic Key West Vacation Rentals has mini Key West getaways for July we're excited to share with you. You've waited a whole year to hit the road and the airways to travel to your favorite destinations and our Caribbean paradise is at the top of...Read more
key west 4th of july
Key West 4th of July fireworks are on for 2021 and you're invited to be here for our Caribbean styled celebration. Bring the whole family to the Patriotic Party by the Ed Knight Pier to celebrate America's birthday. You'll enjoy food, music, and of course,...Read more
key west mermaid festival
The Key West Mermaid Festival invites you to step back in time to an island called Cayo Hueso (Bone Cay), where the Gulf meets the Atlantic, and the captains, seafarers, and fishermen would tell their stories of the sweet Mermaid songs. This fin-tastic five-day event...Read more
key west key lime festival
Key Lime Festival is July 1-5 and it's the sweetest and tartest festival this side of the 7-Mile Bridge in Key West. Be our guests and enjoy a full four days of culinary events for every taste. There'll be a Key Lime Cocktail Sip and...Read more

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