Key West Travel Blog

dreaming on duval
Fantastic vacation rentals for Fantasy Fest are staged and ready to deliver your best Key West stays ever. This outrageous 10-day costuming and masking celebration features dozens of masquerade competitions, themed parties and other exuberant events. The 2022 theme is ‘Cult Classics and Cartoon Chaos!'...Read more
the pink house
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
miss sunshine balcony
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
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
Miss Sunshine Monthly Rental
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
casablanca too facade
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
dreaming on duval
Seafood lovers can chow down on Florida’s clawless lobster during a tasty “feast-ival” 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 festivities celebrate...Read more
the lighted bike parade
The Lighted Bike Parade is ready to pedal loads of Christmas fun into your summertime vacation. Meet up at Twisted Tinsel at 7:00pm Saturday, July 23, 2022 for cookies and cocktails and decorating of the bikes! The ride starts at 8:15pm! The parade will end...Read more
Hemingway Look-Alikes
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
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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