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.

bohemian house pool

14 Key West Spots For The Summer Months

Historic Key West Vacation Rentals has 14 Key West spots available for the summer months. As temperatures rise this time of year, so does the fun and a month, or longer, by the sea is the best way to experience our Caribbean tropical paradise. Our...Read more
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Key West Vacation Guide
the new pool at Cloud 9

Cloud 9 Is All New For Spring

Cloud 9 is all-new for spring and Historic Key West Vacation Rentals invites you to experience the new decor. Just a half-block off Duval you’ll find this secret paradise awaiting you at Cloud 9. When you pass through the whimsical custom wrought iron gate decorated...Read more
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Key West Vacation Guide
key west southernmost point

Key West Festivals, Art and Events

Key West opens up for spring, summer, the arts, live shows and more and you're invited to come down to enjoy it all! Our tropical weather is cooperating just fine and our always beautiful Caribbean Sea is sending waves of welcome for repeat guests and...Read more
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Key West Vacation Guide
key west snorkeling

Key West Is For Snorkelers

Key West is for snorkelers and now is the time to plan your summertime snorkeling adventures in the Caribbean. What better way to enjoy our Key West sunshine than to dive right in? Calm and incredibly flat water in the summer, 100-foot snorkel visibility at...Read more
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Key West Vacation Guide
Villa Luxe entrance

9 Spots For Romance In Key West

We've had our fill of staying home. We've tired of drive-through windows at our favorite restaurants that kept their doors locked. We've said so long to too many of our favorite spaces where we love to laugh, to talk, to eat, to share and to...Read more
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Key West Vacation Guide
Chick A Pea Cottage Bedroom

Positive Guest Experiences

Positive guest experiences are what we're about. Key West is a magical, Caribbean paradise and it's the perfect setting for our collection of luxury boutique vacation rentals. We look forward to welcoming our guests and making their stays exceptional. We want you to know we...Read more
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Key West Vacation Guide
Key West Songwriters Festival

Key West Songwriters Festival Is May 5-9, 2021

Key West Songwriters Festival is May 5-9, 2021 and Historic Key West Vacation Rentals has the finest collection of luxury boutique rentals that hit all the right notes. We'll sing in the sunshine and welcome songwriters from around the world to our Caribbean paradise. This...Read more
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Key West Vacation Guide
the pool at Starfish monthly rental

10 Joys Of Spring In Key West

We're sharing 10 joys of spring in Key West. 2020 was not very joyful, so now it's time to travel, to laugh, to learn, to discover and to relax. Historic Key West Vacation Rentals' collection of luxury boutique vacation rentals welcome to you our Caribbean...Read more
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Key West Vacation Guide
chavez house pool

Sunny Key West Is Something To Talk About

Sunny Key West is something to talk about, especially in winter. While the rest of the country is trudging through snow, sleet, rain, gray skies and quarantines, our Caribbean paradise is sharing the sunshine and good cheer. Our guests have lots of great things to...Read more
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Key West Vacation Guide
solaris cottage den

Solaris Cottage Key West Spotlight

Solaris Cottage debuts new colors for spring and summer and you're invited to join in the celebration for Spring Break, Memorial Day, and summer vacations. Solaris Cottage is located on one of Key West’s most private slow lanes. This tranquil one-bedroom vacation rental was built...Read more
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Key West Vacation Guide

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