Fantasy Fest 2021

Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. It worked. Fantasy Fest has grown every year since its inception and is now the wildest extravaganza around! Fun-loving revelers from around the globe bring their creativity and imaginations as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement! The dates of this year's festival are October 22-31, 2021 and Historic Key West Vacation Rentals has these fantastic cottages and Conch homes with availability.

Casablanca Grande - Nightly Rental 2 Bedrooms 2 Bath Sleeps 6

Casablanca Grande is the perfect get-a-way vacation rental for those seeking a good time, but would like to stay a short distance from all the Duval Street craziness! In addition to the private pool, hot tub, and in-wall A/C, this property also has designated off-street parking for 2 cars (one per unit). With the two units, you can also be close to friends or family but still, have your own private space. Casablanca and Casablanca Too each sleep two adults comfortably. 

Chavez House - Nightly Rental 3 Bedrooms 2 Bath Sleeps 6

This two-story eyebrow house was built in 1870 and is in the National Register of Historic Places. Newly renovated and very well appointed! Fine linens, gorgeous furniture, ultra-comfortable mattresses, and a cool and calming color palette. At 1415 sq. ft. this home comfortably sleeps 6. Enjoy a dip in the new private pool, work on your tan on the large exterior deck!

Harry Truman Suite - Nightly Rental 2 Bedrooms 1 Bath Sleeps 5

New and very comfortable living room furniture so you can lounge while you watch your favorite programs, sports, or use the free high-speed Wi-Fi on your electronic devices. Many of the island's best restaurants are only a short stroll away but if you prefer to stay in, your kitchen is complete with all the appliances, cookware and dishes you need.

Margaret Truman Suite - Nightly Rental 2 Bedrooms 1 Bath Sleeps 5

Our Margaret suite is furnished with a full kitchen, contemporary living room with new comfortable furniture, new ultra-comfortable mattresses with premium linens, bathroom with Travertine shower and in-suite washer and dryer, high-speed Wi-Fi, flat-screen TVs in every bedroom and a large flat-screen TV in the living room - newly renovated and immaculate!

Southard Comfort - Nightly Rental 3 Bedrooms 2.5 Bath Sleeps 6

A pool with a beautiful waterfall feature right off the living room for easy entertaining. Your stay at Southard Comfort would not be complete without enjoying the private outdoor shower. You can start your day with a relaxing shower under the tropical morning sun or end your day showering under the evening stars. It is also perfect for rinsing off the beach sand or ocean salt.

Villa Luxe - Nightly Rental 3 Bedrooms 3.5 Bath Sleeps 7

VILLA LUXE reveals a discreet but sexy glamour beyond its gates––and it’s no wonder, since it was once owned by a hip clothing brand. It’s easy to imagine models and fashion industry types lounging poolside, away from the watchful eyes of others. Now, you can rent it for yourself and your fabulous friends (and everyone’s more fabulous here). This is truly an "Adults Only" property. Not suitable for children under the age of 12.

Expect new innovations designed to keep the festival fresh, relevant and fun, along with a renewed emphasis on encouraging local business engagement and participation, an increased focus on Keys arts and culture, and a commitment to recycling and keeping the festival green. Reserve your cottage or Conch home right on our website or with our fantastic vacation planners. Being an adult has never been more fun!