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.

key west gramping with kids

Concierge Services for Your Key West Getaway

Booking your Key West rental home is just the beginning! Historic Key West Vacation Rentals is here to help you plan your Key West vacation. Our little Key West island offers endless fun-filled activities and events such as water excursions, historical tours, fishing charters, and...Read more
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Key West Vacation Guide
dreaming on duval

I Love Stock Island Festival

I Love Stock Island Festival is June 15-19, 2022. This five-day festival is to feature one-of-a-kind Stock Island-inspired activities and authentic immersive experiences in the local Key West community, culture, and art. It's a great way to celebrate Father’s Day weekend with friends and family...Read more
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Key West Vacation Guide
key west pride

Key West Pride

Key West Pride is June 1-5, 2022. Presented by the Key West Business Guild, events showcase the diversity and welcoming atmosphere that make the southernmost city a top vacation destination for LGBTQ visitors. The festival schedule typically includes pool parties at guesthouses and emporiums, drag...Read more
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Key West Vacation Guide
conch republic independence

Conch Republic Independence Celebration

Every year visitors join Florida Keys residents for the Conch Republic Independence Celebration , a quirky event honoring the birth of the republic and its place in Keys history. The republic was founded in April 1982 to protest the installation of a U.S. Border Patrol...Read more
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Key West Vacation Guide
dreaming on duval

Dreaming Of Key West

Dreaming of Key West and a fantastic luxury vacation to the Caribbean? Dreams do come true in Key West! Be our guests in this private wonderland on the quieter end of Duval Street. Dreaming On Duval has added new high end decor and furnishings just...Read more
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Key West Vacation Guide
Key West 200th Anniversary

Key West 200th Anniversary Celebration

Join the multi-day 200th anniversary of Key West’s first permanent settlement, commemorating the date of March 25, 1822, when U.S. Navy Lt. Matthew Perry planted the American flag on island soil, thereby solidified Key West's special place in history. Celebrate the island's history, architecture, food,...Read more
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Key West Vacation Guide
key west songwriters festival

26TH Annual Key West Songwriters Festival

May 4-8, 2022 is the 26th annual Key West Songwriters Festival in beautiful and historic Key West. It is one of the largest festivals of its kind in the world, and has grown into both a tourist attraction and favorite of island locals. The festival...Read more
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Key West Vacation Guide
VRMA

Celebrating Vacation Rental Week March 7-11, 2022

Historic Key West Vacation Rentals is thrilled to participate in the third annual Vacation Rental Week! Professionally-managed vacation rentals provide value and benefits for guests and property owners alike. This celebration of Vacation Rental Week is our chance to highlight professionally managed properties and to...Read more
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Key West Vacation Guide
my happy place vacation rental

Lower Spring Monthly Key West Rentals

Welcome spring with lower rates on our monthly Key West rentals . We're so happy to see our hours of warmer daylight go up, we're lowering rates on our available monthly rentals for April 2022. Enjoy the drive down to the Keys or schedule your...Read more
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Key West Vacation Guide
Inn Cogneato Monthly Rental

Happy Anniversary To The Conch Republic

The Conch Republic was born on April 23, 1982, in response to a United States Border Patrol Blockade of the Florida Keys. Since the United States insisted on treating the Keys like a foreign country, Mayor Dennis Wardlow seceded from Union. Today we stand proudly...Read more
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Key West Vacation Guide

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