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.

villa josine rain porch

9 Key West Rain Porches

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
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Key West Vacation Guide
cloud 9 pool

End Your Summer In Key West With A Big Splash

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
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Key West Vacation Guide
Starfish Monthly Rental in Key West

Monthly Work From Home Vacation Rentals

Here are 10 monthly Key West rentals 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...Read more
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Key West Vacation Guide
copa cabana

Key West Monthly Summer Cottages

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
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Key West Vacation Guide
cloud 9 den

Mini Key West Getaways For July

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
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Key West Vacation Guide
key west 4th of july

Key West 4th Of July Fireworks

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
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Key West Vacation Guide
key west mermaid festival

The 2nd Annual 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
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Key West Vacation Guide
key west key lime festival

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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Key West Vacation Guide
copa cabana pool

Work, Play And Stay In Key West

Work, play and stay in Key West all summer. Historic Key West Vacation Rentals features luxury boutique vacation rentals that feature free Internet so you can remote work and remote learn. Stretch your Caribbean vacation into your most memorable travel experience. We feature nightly, weekly...Read more
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Key West Vacation Guide
the escape in sunset key

The Escape at Sunset Key - Monthly Rental

The Escape At Sunset Key is now available as a Monthly Rental from Historic Key West Vacation Rentals. Begin to relax and unwind as you ferry between two Keys in less than five minutes. Feel the soft breezes on your face and your tensions melt...Read more
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Key West Vacation Guide

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