Key West Guests Say It Best

Our Historic Key West Vacation Rentals team takes great pride in preparing each property with your comfort and convenience in mind. We don't just make the beds. We're committed to making your stay exceptional and unforgettable.  You can imagine the pride and sense of a job well done when our guests submit reviews filled with compliments and satisfaction.  Our Key West guests say it best and we're listening.

Great Location, Great Property

"My friends and I really enjoyed staying here. Property was clean and updated. Great, quiet location not too far from all the action. Would definitely stay here again. Property Managers were very helpful and responsive." — Guests of Horse Conch

Great Place for a Bachelor Party

"9 guys stayed for 4 days. Walking distance to Duval street. We had an amazing time. The backyard is an incredible entertainment area. House is immaculate. Cindy was incredible! Answering any questions we had by text in minutes. HKWVR are amazing people to work with. Would recommend this location to anyone. Any age group. Looking to have a good time." — Guests of Queen Conch

Amazing Location, Very Comfortable

"This was one of the best vacation rentals we have ever reserved. The location in Key West is absolutely unmatched! It’s right in the heart of the action but somehow tucked away and private. We only used our rental car twice in 7 days, once to get to a kayak excursion and once to the grocery store. The neighborhood is incredibly picturesque, like straight out of a movie. Beautiful landscaping everywhere and super clean and well maintained. The pool is very nice but small, we had it all to ourselves most visits. Do yourself a favor and rent bikes, we used them every day multiple times per day. The Concierge, Cindy, was so friendly and very very helpful. We had a minor issue during our stay and it was handled quickly with no inconvenience to us at all. We will definitely stay here again, no doubt about it." — Guest of Fair Winds at the Foundry

Above and Beyond Our Expectations

"This home was pristine! The pool was fantastic and we spent a lot of time in it. We were in close proximity to Duval and there were several restaurants and shops just blocks away from us. Both the cottage and the two-story villa were simply spectacular. The house was incredibly clean. In fact, I have never seen a house more clean for a vacation stay. The Decor is very Unique and you won’t be disappointed. The vacation rental company went above and beyond our expectations and met our every need. We loved the fact that all of us had our own bed and bathroom. This is a true gem in Key West and I highly recommend this property." — Guests of Villa Luxe

The Location is Perfect

"It's a beautiful home, very nicely furnished. We were a multigenerational party of eight and there was plenty of room. The location is perfect — on Duval, but at the quiet end; an easy walk to the action." — Guests of Grand Maison

Will Not Disappoint

"I have rented houses in Key West and I usually stay somewhere different just to try. Well folks I don't think that will happen again. This place is 'Top Shelf.' It's perfect for 6 people to have their own sleeping space, yet enjoy the Chefs kitchen and huge den, dining, and fantastic porch. Yes, this place is a bit more expensive than others, but it will not disappoint you." — Guests of Villa Luxe

Highly Recommend

"We cannot say enough about Fair Winds at the Foundry! The property is fantastic - super close to everything in Old Town but you feel like you are in the midst of the jungle with all of the tropical plants/trees. The layout of the townhome is great for families or two couples - and it was spotless. I really appreciated the way that Historic Key West Vacation Rentals worked with us as we were booking for the time right after the island opened back up in June. They were super accommodating and very transparent with everything they did/said. We will definitely stay there again and highly recommend it!" — Guests of Fair Winds at the Foundry

The Grounds Were Lovely

"Becky and I had a fantastic time and loved the property. It was quiet; the grounds, lovely; and the hot tub was amazing. We would love to reserve for a week in May 2021. Let us know when bookings open up and how to proceed. Thanks so much!" —Jeremy, Guest of Poinciana Garden

Walk to the Best Restaurants

"We had a great trip and stayed at the Bess suite / Truman house. 2 year old updated house with nice porch and nice finish out. My wife and I really liked its central location. Walk to the best restaurants. Phil and Sam know the island and offer great advice during your stay." — Grant L., Guest of Bess Truman Suite

Discover Historic Key West Vacation Rentals

Historic Key West Vacation Rentals is proud to offer luxury historic vacation rental homes in Key West, Florida. Our well-trained vacation specialists will guide you through the important process of selecting just the right property for your stay. Whether your party is one of friends or family, or a group celebrating a special occasion, we are eager to help you find the ideal property among our exceptional selection of beautiful accommodations.