Vacation Homes of Key West - VHKW

01/30/2026

We only have 4 rentals left for March! 🌴☀️
3 are brand new to our inventory, and we’re so excited to finally share them with our fellow Key West–loving friends.
Prices reflect lower last-minute rates, so don’t wait—book now before they’re gone! Contact our team if you have any questions ☺️ 305•294•7358

• Bella Grand Premier Estate- 5 BR 5.5 BA
• Key of Blue- 4 BR 3 BA
• Washington Villa- 3 BR 3.5 BA
• Sun, Sea, & Citrus- 2 BR 2 BA

12/15/2025

Fill your camera roll with the best family vacation memories when you stay at The Kaleidoscope House: A Colorful Key West Hideaway. Tucked away on a quiet, foliage-lined street in Old Town, this vibrant tropical retreat is nestled in and amongst the best of Key West. This home is a newer construction, built in 2006, with a big porch, vaulted ceilings, and a calming sage green exterior. Inside, bold and bright design details create a playful yet serene atmosphere, perfect for everything from post-beach, lazy lunch breaks to lively evening get-togethers before you head out on Duval Street.

Make your way down the artful, turquoise entry hallway and you’ll notice this home is well-stocked with all you need for a great time. Carts and wagons for the beach, yoga mats, towels, boogie boards, and cabinets full of snorkel gear, pool toys, games for game night, books and more.

Did we mention the gorgeous garden, large pool and outdoor shower!?

We love this home! Come stay with us soon.

✈️

11/21/2025

If you needed a sign to book a November trip to Key West, this is it. Come stay in one of our unique vacation rentals and get out on the water with the help of our local concierge.

11/18/2025

One of the best parts of this business is when our guests opt for personalized add-on services like decor for a surprise birthday, anniversary, retirement, babymoon, bachelor/bachelorette party… you name it!! It is so rewarding for us to hear how delighted guests are upon walking straight into a celebration. We love coordinating these moments knowing it makes your Key West vacation that much more memorable. 💐🎉 Contact us via our website if you are interested in planning your perfect celebratory Key West getaway with the help of our local concierge. 🌺

11/03/2025

One of our most epic and beloved properties now has availability yet this winter! The Octagon House of Key West situated prominently in the Historic Seaport neighborhood and is a stunning piece of architectural restoration and preservation.

In 1976, this property was already 90 years old and dilapidated. But when its unique octagon shape caught designer Angelo Donghia’s eye, he immediately envisioned its potential for awe and magnificence. He bought it for $45,000 and spent 2 years restoring it with care, intention, and craftsmanship. By the time Calvin Klein purchased it from him in 1981, it was worth almost $1 million- more than 15x the original price Donghia had paid. Though Klein sold it in 1987, it is still sometimes referred to locally as “The Calvin Klein House.”

Today, we are honored to manage it and share it with guests who love Key West and its history. It is an absolute island living masterpiece with 4 bedrooms, 4 bathrooms, lush gardens, a serene private pool, iconic wraparound porches, and elegant interior harmony sustaining from Donghia’s enduring designs. Check out the entire listing on our site for a deeper dive into its history, amenities, and current availability!

11/02/2025

Thank you to all our guests who and stayed with VHKW for Fantasy Fest week and Halloween weekend!! See you next year, or even better, come back sooner!! 🌺💛

08/23/2025