Little Miss Magic - Monthly Rental

key west vacation rental, sleeps 7, Cloud 9,
The Pink House - Monthly Rental
Steamplant 212 - Monthly Rental
Chavez House, key west vacation rental, private pool, sleeps 6,luxury home



Discover Boutique Rental Homes In Key West

Welcome to Key West, a sunny and picturesque island town in the Florida Keys. Locals and visitors alike love Key West for its pastel-colored homes, great fishing and fresh seafood, snorkeling and scuba diving, quaint streets, and fun events and nightlife. Our properties are mainly located in the Key West Historic District, on the western side of the island. This desireable area (also known as Old Town) has charming architecture, as well as top points of interest. 

Find Your Ultimate Key West Accommodations

Live like a Floridian with our luxury Key West homes, condos, and cottages. These properties, which range from one to six bedrooms, offer spacious interiors, ideal locations, equipped kitchens, and free high-speed internet. Other convenient amenities include available on-site check-ins, refreshing private pools, and outdoor showers. Some properties are even pet friendly! Whether you're just traveling through or are planning to stay a month or more, we have the Key West home for your needs. 

Search our nightly rentals, weekly rentals, and monthly rentals to find the perfect accommodations for your Key West vacation. 

Why Book With Us?

Book directly with Historic Key West Vacation Rentals, a locally owned and operated company, and get the best rate on our properties. Our selection of white-glove tested and impeccably maintaned homes sets us apart from other vacation rental companies. Need help planning your Key West vacation? We're happy to help you find the perfect Key West rental home. And, our experienced and passionate staff can offer a personal touch with local knowledge and recommendations for the area. Start searching our properties or learn more about Historic Key West Vacation Rentals.