Five Premier Vacation Rentals In Key West

premier vacation rentals in key west
By the Historic Key West Vacation Rentals Team

Key West is open and we are excited to see our guests again. Our collections of cottages, condos, and homes have been scrubbed, sanitized, and styled with you and your social distancing needs in mind. We have cozy and intimate smaller rentals for solo travelers and couples retreats. Our larger homes and vacation compounds are perfect for family fun, girls getaways, mancations, and for meeting up with other friends and family you've haven't seen in a while. Which rental is best for you? Virtually tour our entire collection right on our website or connect with our very experienced Vacation Planners to help you decide. We're featuring five premier vacation rentals right here. They're all great places to live like a local.

Potter's Cottage - Nightly Rental 2 Bedrooms 2 Bath Sleeps 5

Experience hotel-like 5-star luxury but with the exclusive privacy of this adorable Key West home. This super cute home boasts all the amenities you would expect from a luxury hotel including a concierge and high-speed Wi-Fi. At the same time, you can live like a local by taking advantage of the fully equipped kitchen. Enjoy the privacy our tucked-away location affords smack dab in the middle of Key West’s oldest neighborhood.

Seas The Day! - Weekly Rental 2 Bedrooms 1 Bath Sleeps 4

This newly updated first-floor condo is located in the Shipyard section of the Truman Annex facing Southard Street. Open up the French doors to your living room where you will find new and comfy furniture, a flat-screen tv, cable, and wifi.

Little Truman Cottage - NEW Nightly Rental 1 Bedroom 1 Bath Sleeps 2

This cute, cozy, NEWLY CONSTRUCTED cottage features top-of-the-line amenities and brand new furnishings. Little Truman Cottage offers a comfy King-sized bed, large flat-screen TV and vaulted ceiling to give the space an extra roomy feel. There is rich, hardwood flooring throughout, a convenient TV tray, a dresser, a large mirror, and bedside lighting.

Chavez House - Nightly Rental 3 Bedrooms 2 Bath Sleeps 6

This two-story eyebrow house was built in 1870 and is in the National Register of Historic Places. It's been newly renovated and very well appointed! Guests love its fine linens, gorgeous furniture, ultra-comfortable mattresses, and a cool and calming color palette. At 1415 sq ft this home comfortably sleeps 6. Enjoy a dip in the new private pool, work on your tan on the large exterior deck!

Southard Comfort - Nightly Rental 3 Bedrooms 2.5 Bath Sleeps 6

This is true Island living in Historic "Old Town" Key West. When you walk into the living room, you’re just a few steps from the pool with its custom waterfall. The expansive French doors can be left open to make the most of those tropical breezes. On really warm days, close up and relax with the central air conditioning.

How great will your next Key West Vacation be? Our vacation rentals have been sanitized according to CDC guidelines, so all you have to do is come on down and live like a local. During your visit, please adhere to our guidelines and respect the health and safety of our Key West residents. Expect to have your temperature taken before entering restaurants and shops and remember that masks are required for entry into all establishments. Now, come on down, wash your hands frequently and enjoy your visits. We've been missing you!