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.

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 by the high-end kitchen, natural light, and hardwood...Read more
miss sunshine parking
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 more
Miss Sunshine Monthly Rental
The eight best Snowbird luxury rentals in Key West and are available through Historic Key West Vacations Rentals. They're the best because they're located in this tropical paradise surrounded by crystal blue waters separated from the high octane speed of life on the mainland. All...Read more
villa azul
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