Key West 200th Anniversary Celebration

Join the multi-day 200th anniversary of Key West’s first permanent settlement, commemorating the date of March 25, 1822, when U.S. Navy Lt. Matthew Perry planted the American flag on island soil, thereby solidified Key West's special place in history. Celebrate the island's history, architecture, food, culture, art, industries, residents and more. Planned activities include historical events, talks and shared history, a parade, heritage festival, fireworks, even a time capsule intended to be reopened at the 250th celebration in 2072. It all takes place March 19-30, 2022 and you're invited to be our guests.

Chick-A-Pea is a traditional Key West cottage that has undergone a complete renovation. The charm and historic features have been retained, while all the luxuries of today have been added. Two great features of this house are the pool and cabana. There is deck space around the pool that is great for sunning. There is a propane grill for outdoor cooking. The pool cabana is covered and has a sofa and lounge chairs. This is the perfect spot for an afternoon cocktail or nap!

Dreaming on Duval will accommodate your crowd. With three levels of gorgeous living there is plenty of space for everyone to stretch out. The first floor includes the family room, kitchen, powder room, and study-a suitable place to work/school virtually or enjoy a quiet read. A first-floor king bedroom with luxurious ensuite bath walk-in shower is ideal for the in-laws. The tropical outdoor area has shaded areas for sitting and dining, as well as sunny areas for lounging by the private pool. Enjoy the sound of the waterfall feature while sipping on a cocktail or cooking on the gas grill. In no time, you will know why this house was featured on HGTV’s House Hunters.

This comfortably furnished second-floor duplex home comes with Key West charm and contemporary touches. Walkable to many shops and attractions, you will feel like a local in no time. Enjoy coffee or cocktails on your covered porch with a treetop view.

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 a luxurious, "Adults Only" property.

Join in the celebration for Key West's 200th Anniversary! Browse our nightly, weekly, or monthly luxury rentals and book your luxury vacation rental with our experienced vacation planners!