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.

Cloud 9 pool

5 Dream Adventures In Key West

While most everywhere else is making preparations to winter up and hibernate until the spring thaw, Key West continues to be sunny and warm with breathtaking sites that draw crowds every night for the sunsets, arts, recreation and culinary spectaculars. Our Conch Republic is one...Read more
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Key West Vacation Guide
Inn Cogneato pool

Inn Cogneato Cottage - Monthly Rental

Inn Cogneato is a beautifully renovated two-bedroom, two-bath home located in one of the oldest parts of Historic Key West. Surrounded by a white picket fence and with its gorgeous wood floors, this home is perfect for a couple that plans on entertaining visiting guests...Read more
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Key West Vacation Guide
Reel Paradise

Reel Paradise

Reel Paradise invites its guests to enjoy the peace and serenity of island life. This beautiful home is so warm and inviting! As you enter the gate, you will pass by the shared pool and gardens on the way to your covered front porch. Step...Read more
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Key West Vacation Guide
the pool at Dreaming On Duval

4 Guests' Inspirations For Fall Key West Vacations

Historic Key West Vacation Rentals has enjoyed seeing so many of our repeat guests we didn't get to see last year, and now we're even more anxious to see more of our guests we've come to cherish and enjoy. Even though the calendar may be...Read more
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Key West Vacation Guide
The Truman Suites

The Truman Suites

The Truman Suites offers five separate fully equipped suites just a few steps from famous Duval Street. The two-story complex offers seven bedrooms, five bathrooms and sleeps up to 18. The Truman Suites collection includes 1-2 bedroom suites — Harry, Margaret, Martha, Bess Suites, and...Read more
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Key West Vacation Guide
key west's southernmost point

5 Remote Working Breaks In Key West

This is the life. Remote working from a luxury boutique cottage or Conch home with the Caribbean and historic Key West as a part of your office decor. Historic Key West Vacation Rentals has the perfect home away from home for you and your friends...Read more
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Key West Vacation Guide
Fantasy Fest

Fantasy Fest 2021

Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. It worked. Fantasy Fest...Read more
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Key West Vacation Guide
kids key west

Gramping In Key West

Gramping in Key West is a grand idea whose time has come. Also known as a skip generation vacation, grandparents are now enjoying getaways with their grandchildren. The ability to remote work and to remote learn adds to the allure for grandparents to be more...Read more
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Key West Vacation Guide
Bohemian House lanai

Annual Key West Brewfest

Brewfest is a fun festival developed to benefit the Key West Sunrise Rotary and it's coming up September 2-6, 2021. These funds allow the club to provide yearly educational scholarships to local students and charitable donations to other non-profit organizations. In addition to raising funds,...Read more
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Key West Vacation Guide
Sea Vista pool

Key West WomenFest

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
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Key West Vacation Guide

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