Key West vacation rentals offered exclusively by Vacation Homes of Key West. Browse our unique vacation rental homes including conch cottages, condos, villas & luxury estates with private pools.

Explore our exclusive selection of Key West vacation rentals, from historic conch homes to luxury waterfront retreats. Find the perfect island getaway today!

Experience true tropical Key West living as the locals do in this spacious mid-century private garden oasis home with large swimming pool and poolside entertainment cabana. Located just one block …

Ocean View Luxury Villa in Key West offers an exceptional vacation experience with both stunning ocean views and easy beach access. Nestled in the upscale gated community of Truman Annex, this …

Key West Vacation Rental Enhanced COVID-19 Cleaning Protocols at VHKW ~ Vacation Homes of Key West Key West Vacation Rental Why ‘Book Direct’ with a Local Vacation Rental Company rather …

Discover why Vacation Homes of Key West has been Key West’s trusted vacation rental experts for over 25 years—offering handpicked homes, expert management, and unforgettable island experiences.

Stay in Downtown Old Town Key West, where historic charm meets vibrant energy. Enjoy top dining, shopping, nightlife, and iconic landmarks just steps away.

Area: The center district of Old Town Key West is the “residential heart.” Historic streets are lined with more and more wooden Victorian homes and cottages built by early ship builders and men of wealth.

One of the best vacation rental locations on the island. Around the corner “Grand Vin” wine bar stands ready for an evening wine tasting session while “Flamingo Crossing” ice cream parlor offers up a …

Choose a monthly rental and stay for a while. The chance to stay longer is every vacationers dream. Click here to view our rental listings, you can sort them by monthly and weekly rentals with the “Rent …