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!

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 …

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

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 …

Escape to Sunset Key, a private island paradise in Key West. Book an exclusive vacation rental with ocean views, pristine beaches, and ultimate tranquility.

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 …

Experience the charm of Truman Annex in Key West! Book a vacation rental in this historic, gated community near top attractions, beaches, and lively Duval Street.

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 …

Escape to The Kaleidoscope House in Old Town Key West—vibrant design, private pool, and relaxing island vibes for the perfect family vacation.