Historic Key West Vacation Rentals

“We very much enjoyed our stay at Southard Comfort! The home was inviting and comfortable from the moment we stepped inside. All amenities were as described and the cocktail pool was our favorite place to spend time together after a busy day or evening. HKWVR could not have been more friendly or attentive or helpful from the minute we made the reservation till the time we got in the car to leave. I highly recommend both the house and the rental company. Can't wait to visit again.”

“We had a great stay and would absolutely come back. The location was one of the biggest highlights. It was peaceful and relaxing while still being incredibly walkable and convenient to everything we wanted to do. Having access to the pool made the trip even better, especially after long days out exploring. The hosting company was also fantastic to work with throughout the stay: very friendly, responsive, and accommodating. Overall, a really easy and enjoyable experience from start to finish.”

“Wow! Flamingo Cottage was just perfect for a fun getaway to Key West! Check-in after hours due to our flight was a breeze, the cottage was just as described/pictured, and the service was absolutely exceptional. Shout out to Cindy at HKWVR who managed our visit beautifully!”

“Excellent stay. The responses were immediate whenever I had a question. The house, pool, washer & dryer were perfect.”

“We enjoyed our stay at this Key West cottage! The cottage was very clean, air conditioner worked great! We enjoyed lounging by the pool after a day of sightseeing. In the morning we sat on the front porch with coffee. Our communication with the host was also very easy. I would def stay here again.”

“Staying at this place was a true rare find - in a town that is getting more and more crowded by the year, this place felt simultaneously peaceful but also close to all the action. Perfect amount of space, felt like we really got the key west porch vibe. We were there for a family engagement- and having this as our home base was awesome. Beds were super comfy, A/C was powerful, couch room was perfect for wfh, and lots of light. Text comms with rental company was great - we’ll come back in a heartbeat! And proximity to Cuban Coffee Queen was clutch.”

“A wonderful historic home. Bedrooms were nice. Kitchen was stocked well for cooking except for spices, wraps. Living room was pleasant. Loved the neighborhood. Easily walkable to many places. Southard St is a one way off of White St directly to downtown so morning was a little busy for a couple of hours from the front porch. Part of the neighborhood vibe. But inside the house and in the pool yard was super quiet separate world. Pool was important and nice. Temperature was tough to regulate but very minor. House was nice accommodating three couples comfortably.”

“Just as advertised, this place was amazing.”

“We had a great week in Key West with our teenage children at this property at the quiet end of Duval. Very comfortable, thoughtful details, and easy. There’s a wonderful bakery across the street for grabbing breakfast. Lots of great bars and restaurants within walking distance. One reviewer noted that there was a loud club across the street that was open very late. We were there five nights, the club was only open one of those nights (Sunday night). We were able to mostly drown out the noise with the AC fan and fans in the bedrooms. It definitely did not distract from our overall visit, which was lovely. Would definitely stay here again.”

“An extremely nice property, right of Duval street. Host has firm policy on check in and check out. If traveling with children, note there is a strip club across the street. It is also very loud at night.”