Key West WomenFest

The southernmost party for women and their friends is in Key West, presented by the Key West Business Guild.  WomenFest has a simple goal: to celebrate ALL women! Key West WomenFest offers a wide range of activities for those who want to socialize, feel comfortable being themselves, soak up some sun, then party and dance the night away. Since its introduction over 20 years ago, Key West WomenFest has grown to become a standard for celebrating women ranging from all ages 21 and over. Couples, singles, and those in between are all welcome!

Historic Key West Vacation Rentals welcomes you and invites you to experience our collection of boutique luxury vacation rentals for the week and to stay on for the whole month or longer! We feature accommodations for single travelers and couples. as well as larger homes for a group of friends, too.  Here are some very fine examples of the cottages, condos, townhomes, and conch homes we have available.

Fair Winds at the Foundry is a gorgeous,  coastal 3 story immaculate light and airy end unit townhouse in the Foundry section of the Truman Annex. Walking distance to ALL that Key West has to offer!

Every step outside Ashe House leads to the richness of Key West’s charm and beauty––lush tropical foliage, picket fences, gingerbread trim––while indoors the home is stunningly renovated and plumped with island-living comfort.

Built in the shotgun style, the home’s front door enters a hallway that extends to the back of the house with a master bedroom and adjoining bath, as well as a guest room and adjacent second bathroom built off the left side. This architectural device both harmonizes indoor and out space and ventilates the rooms, as was necessary for days before air-conditioning.

 Explore the beautiful outdoor deck that opens through French doors from the spacious, well-appointed kitchen. Why, there’s even that desirable and private outdoor shower with stars and moonlight overhead each evening.

Ever dream of waking up, walking out your back door, and taking a peaceful morning kayak trip or afternoon stand-up paddleboarding? This home is unique in that it not only has a private heated swimming pool, but it also has a put-in for your kayak or paddleboard with your own DOCK that will accommodate a small fishing boat or a small johnboat! Just beyond your back gate is a walk-in launch!

Southern Skies is the Great Old Town location you want for your friends' getaway! A heated pool with a waterfall is private and luxurious. This home is just a 4-minute walk to the Southernmost Point of the United States, and just a few minutes by bike to Duval Street and all it has to offer.

Spacious open floor plan with travertine marble floors. Skylights and lofty 14' ceilings complement the 2924 square feet of interior living space. Add the expansive balconies and rooftop terraces and this home is one of the largest monthly vacation rentals in Key West. Each large bedroom has its own ensuite state-of-the-art bath. The floor-to-ceiling sliding glass doors open each bedroom to a private balcony. Extra-large walk-in closets will accommodate an extensive wardrobe. 

These are just some of the luxury boutique vacation rentals we have available for Womenfest and your end-of-summer and fall getaways.  See more of our collection, including information, photos, amenities and rates right on our website.  You can even reserve your favorite online or with our experienced vacation planners. See you soon!