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Key West Vacation Guide

Your Guide to Old Town Key West

  Imagine stepping into a tropical paradise filled with vibrant colors, rich history, and the rhythmic charm of island life. Welcome to Old Town Key West—a place where every street corner has a story to tell, and every home whispers of times (read)

Published on Oct 13, 2024

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Key West Vacation Guide

Christmas Events in Key West

Your Guide to a Tropical Holiday Celebration If you're searching for a tropical twist to your holiday season, look no further than Key West. With its warm weather, festive lights, and unique island charm, Key West is the perfect escape from traditional (read)

Published on Sep 08, 2024

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Key West Vacation Guide

Christmas in Key West FL

  A Festive Celebration with a Tropical Twist If you're seeking a holiday season like no other, look no further than Christmas in Key West FL . Imagine twinkling lights wrapped around palm trees, Santa trading his sleigh for a jet ski, and tropical (read)

Published on Sep 03, 2024

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Key West Vacation Guide

Discover Key West Architecture

A Rich Tapestry of Key West Architecture Styles Conch Houses: Iconic and Historic Key West’s Conch houses are a testament to the Florida keys rich architectural history. Dating back to the early 19th century, these homes blend Caribbean and American (read)

Published on Aug 04, 2024

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Key West Vacation Guide

Key West Adventures

When it comes to stunning destinations that create unforgettable moments that live in your mind long after an Instagram post fades into digital obscurity, Key West tops the list.  There's no place quite like it. Surrounded by the serene beauty of the Florida (read)

Published on Jun 23, 2024

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Key West Vacation Guide

42ND ANNUAL CONCH REPUBLIC DAYS

Fans and friends of the Florida Keys’ Conch Republic can celebrate the irreverent "nation's" 42nd birthday with activities including a tall ship pirate adventure, traditional shrimp boil, sunset boat parade, tour of the USCGC Ingham floating (read)

Published on Mar 25, 2024

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Key West Vacation Guide

Key West Day Trips

What's not to love about day trips during your vacation stays in beautiful and historic Key West? You're on vacation, so no one wants to lug around luggage, overstuffed bags, and all the other paraphernalia our overworked minds tell us we must have any (read)

Published on Feb 21, 2024

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Key West Vacation Guide

Key West's Tranquil Autumn Vibes

It may stil feel like summer in Key West, but just know fall is here. Our Conch Republic has all things delightful and frightful for munchkins, monsters, pumpkin eaters and masqueraders alike. You can unlock the fall magic by being as adventurous as (read)

Published on Oct 18, 2023

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Key West Vacation Guide

5 Fishing Charters In Key West

Charter Fishing in Key West, Fl Key West is renowned for its exceptional fishing opportunities, especially in the bountiful waters of the Gulf Stream. Whether you're a seasoned angler or new to the sport, a fishing trip in Key West promises an unforgettable (read)

Published on Apr 17, 2023

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Key West Vacation Guide

Best Key West Restaurants

Some people live to eat and many of us eat to live. Luckily, Key West is the best place to enjoy Floribbean cuisine and that means no matter why you eat you'll always enjoy a foodie adventure. Since at various times there have been European, Asian, and (read)

Published on Apr 01, 2023

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Key West Vacation Guide

Spend A Month In Key West

Our monthly luxury vacation rental homes in Key West  are the perfect option for an extended stay in our tropical paradise. Immerse yourself in the warm and tropical paradise all month long and experience all that  local living in Key West (read)

Published on Feb 28, 2023

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Key West Vacation Guide

5 Best Key West Spring Retreats

While most are still dealing with colder weather, Key West is more than delighted to invite you to shovel sunshine. Spring in Key West is truly paradise. It's our delightful warmth and wonderful sunshine that create this twist that defies colder temperatures (read)

Published on Jan 04, 2023

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Key West Vacation Guide

Key West Winter Rental Savings

Happy Holidays to you!  Historic Key West Vacation Rentals is proud to announce seven opportunities for seasonal savings in December 2022. We've lowered the rates of all of our remaining Key West monthly rentals through the end of the year. Key (read)

Published on Nov 12, 2022

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Key West Vacation Guide

Fall Savings For Fantasy Fest

Enjoy our new fall savings for Fantasy Fest October 21-30, 2022. We've lowered the nightly rates for our remaining luxury vacation rentals and we invite you to be our guests this festival season.  Cult Classics and Cartoon Chaos is the theme for (read)

Published on Oct 11, 2022

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Key West Vacation Guide

Introducing Magical Margaret

Introducing Magical Margaret, the newest Key West monthly rental to join our luxury vacation rentals collection. It's available for your fall and winter vacations beginning November 2022.  As you enter the main home you will be captivated (read)

Published on Sep 22, 2022

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Key West Vacation Guide

A Virtual Tour of Miss Sunshine

A virtual tour of Miss Sunshine is just the glimpse of one of the best places to stay on your Key West Vaction . Historic Key West Vacation Rentals' Key West Monthly Rentals  are the perfect option for an extended stay in our tropical paradise (read)

Published on Sep 18, 2022

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Key West Vacation Guide

Make A Date With Miss Sunshine

Make a date with Miss Sunshine from our monthly rentals collection and invite your family and friends along for 28+ nights this fall and winter. Make October through February your months for an extended holiday or bring your team down for a work remote (read)

Published on Aug 19, 2022

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Key West Vacation Guide

Fall In Love With Villa Azul

Fall in love with Villa Azul when you reserve it for 28+ nights this October 2022 at our newly reduced monthly rate!  Villa Azul consists of two separate buildings; a main house and a separate pool house! The main house is a two-story historic cottage (read)

Published on Aug 14, 2022

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Key West Vacation Guide

Lighted Bike Parade

The Lighted Bike Parade is ready to pedal loads of Christmas fun into your summertime vacation. Meet up at Twisted Tinsel for cookies and cocktails and decorating of the bikes! The ride starts at 8:15pm! The parade will end at 9pm at 22&Co for (read)

Published on Jul 19, 2022

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Key West Vacation Guide

Hemingway Days

Ernest Hemingway fans can celebrate the late author’s literary accomplishments and colorful Key West lifestyle Tuesday through Sunday, July 20-25. The annual Hemingway Days festivities salute the legacy of the Nobel Prize winner who lived and wrote (read)

Published on Jul 03, 2022

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Key West Vacation Guide

Key Lime Festival 2022

America’s Favorite Citrus Celebration is June 30-July 4, 2022. We like to celebrate the things that make our islands unique. Citrus, eccentrics, people and pie. Our celebrations are fun, odd and unforgettable. Our people are too. Come on down to (read)

Published on Jun 28, 2022

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Key West Vacation Guide

CFK Swim Around Key West

The Key West Open Water Swims will begin after the start of The College of the Florida Keys Swim Around Key West .  June 17 and 18, 2022, embark on an adventurous swim, This is a 12.5 loop around the island with fantastic landscape views of Key West (read)

Published on May 29, 2022

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Key West Vacation Guide

Snorkel Key West All Summer

Snorkel Key West all summer long.  Did you know summer is when the waters around our Conch Republic are most clear and calm? What better way to enjoy our Key West sunshine than to dive right in? Our concierge Cindy will introduce you to (read)

Published on May 19, 2022

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Key West Vacation Guide

Non-Stop Flights to Key West

Getting to Key West can be fun and magical. Making the drive from Miami to our southernmost point is among the most extraordinary, but the Conch Republic is happy to welcome guests from all over. Getting here is easier than ever and these are the non (read)

Published on May 01, 2022

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Key West Vacation Guide

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 (read)

Published on Mar 31, 2022

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Key West Vacation Guide

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 (read)

Published on Mar 30, 2022

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Key West Vacation Guide

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)

Published on Mar 23, 2022

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Key West Vacation Guide

Key West Time Capsule Gala

Key West is celebrating its 200th Anniversary this year. Enjoy a re-enactment of the date of March 25, 1822, when U.S. Navy Lt. MatthewPerry planted the American flag, commemorating Key West's first permanent settlement. Staged at Mallory Square (read)

Published on Feb 13, 2022

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Key West Vacation Guide

Pole Vault In Paradise

Pole Vault in Paradise brings together pole vaulters from age 9 to 75 to compete alongside some of the best pole vaulting elites from around the country. Sponsored by the nonprofit Key West Track & Field Club, the event is to be staged at Higgs Beach (read)

Published on Dec 29, 2021

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Key West Vacation Guide

Tis The Season In Key West

The holiday season is upon us, and Key West invites you to share in our festive celebrations. The season kicks off on Wednesday, November 24th at 5 p.m. with the Lighting of the Harbor Walk of Lights at the Historic Seaport.   The first Monday after (read)

Published on Nov 15, 2021

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