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.

the pink house

The Pink House Is Our December 2022 Showcase

The Pink House is our December 2022 showcase luxury rental and Historic Key West Vacation Rentals invites you to be our guests for 28+ nights. Taking an extended stay in Key West is easy as it’s one of the warmest places in the USA in...Read more
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Key West Vacation Guide
miss sunshine balcony

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, team...Read more
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Key West Vacation Guide
villa azul

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 more
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Key West Vacation Guide
Miss Sunshine Monthly Rental

Miss Sunshine Monthly Reduced Rates

Miss Sunshine Monthly Rental has reduced rates for September 2022. Reserve your minimum 28-night minimum stay on our website or with our vacation planners and use code 10OffSeptMonthly for 10% off your monthly rate! Browse our Key West event calendar for inspiration when planning your...Read more
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Key West Vacation Guide
casablanca too facade

Reserve Casablanca Too For The Holidays

Enjoy the Key West Holidays and reserve Casablanca Too to enjoy a fabulous lower monthly rate when you stay 28 nights or longer in November or December 2022! This luxury boutique cottage is actually a nightly rental, but when you reserve it for extended stays...Read more
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Key West Vacation Guide
dreaming on duval

Where to Stay for Key West Lobsterfest

Seafood lovers can chow down on Florida’s clawless lobster during a tasty Key West Lobsterfest that features a savory schedule of events ranging from a traditional lobster boil to a lively street fair starring the sensational crustacean prepared in a variety of ways. The flavorful...Read more
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Key West Vacation Guide
the lighted bike parade

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 Bad...Read more
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Key West Vacation Guide
Hemingway Look-Alikes

Hemingways To Gather In Key West

The Hemingway Days festival’s undisputed highlight is the Hemingway® Look-Alike Contest at Sloppy Joe’s Bar, a frequent hangout for the writer during his 1930s residence in Key West. Scores of stocky, bearded entrants are to parade across Sloppy Joe’s stage before a judging panel of...Read more
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Key West Vacation Guide
Hemingway Days

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 on the island for most of the 1930s...Read more
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Key West Vacation Guide
4th of July Rotary Club Fireworks

Rotary Club of Key West Independence Day Fireworks

Since 1976, the Rotary Club of Key West has presented the island’s annual fireworks show . Staged from the Edward B. Knight Pier overlooking the Atlantic Ocean at 1800 White St., fireworks are to begin at 9 p.m. Attendees can purchase drinks and food including...Read more
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Key West Vacation Guide

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