The Best Part Of Historic Key West Vacation Rentals

We're sharing some of our favorite cottages, condos, townhouses, Conch homes, and compounds — and some of the very kind words from our guests who love them, too. Historic Key West Vacation Rentals is dedicated to the satisfaction of our homeowners, rental guests and our employees. Don't just take our word for it! Enjoy reading what our guests have to say.

We Would Gladly Stay Here Again

We are a family of four, 2 adults, 11-year-old, 8-year-old and had the perfect stay at Truman Annex, in the unit located at 202-8 Southard. The location is just two blocks off of Duval which makes walking anywhere very easy. We never took a cab or Uber to get anywhere in Old Town. We were able to have our groceries delivered via Instacart from the local Publix store. Plus, a small chain of grocery stores, Fausto's, has a location just three blocks from the condo. The condo itself is very clean and has two queen size beds and a sofa that is comfortable for one person to sleep on. The unit has been recently updated and has a fresh feel to it. The outdoor patio area is amazing, not all units in the Truman Annex have this luxury! We all enjoyed the pool area and the short walk to the splash pad (btw, the splash pad is not like the ones we are familiar with. The one in KW is extra for sure. It's more like a small water park!) The folks at Historic Key West Rentals are amazing: they respond quickly to all communications, they are proactive in reaching out about possible questions we might have, they offered additional services free of charge (and for which they do not receive a commission on). We recommend this unit and booking directly through Historic Key West rentals, instead of VRBO, b/c you will save money!! — Guests of Seas The Day!

Totally Perfect!

My fiancé and I stayed for a month at the Bohemian House and we absolutely loved it! Great location, walkable to almost everything. The pool and backyard were wonderful to have, especially when we had guests. Totally perfect! — Guests of Bohemian House

Lots of Amenities

This house is so beautiful! They made excellent use of the space. We had 9 ladies and didn’t feel cramped at all. The house was super clean and had lots of amenities and touches that we appreciated having available. Check-in and out was quick and easy. Cindy is very responsive and helpful, we appreciated her communications before and during the trip. — Guests of Maisons de Luxe

Beautiful and in a Great Location

Cindy was wonderful to work with and offered great local tips. The place itself was beautiful and in a great location. I would highly recommend staying here! — Guests of Solaris Garden

All the Amenities We Needed

The rental experience was very simple and positive. The hosts were very friendly, responsive and gave lots of helpful information. We came shortly after KW reopened to tourists so they made sure we knew what we going on, open, processes, etc. The house itself was beautiful and had all the amenities we needed to get through the week. We had one small issue that they were quick to respond to and handle, which we greatly appreciated. — Guests of Maisons de Luxe

Beautifully Decorated

This was a beautifully decorated place close to everything in Key West. We stayed in the upper unit. It had everything we needed at an affordable price. I only wish it had a pool and it would have been perfect! We arrived on the Key West Express early in the day and the ladies were nice enough to allow us to drop our luggage off at the office while we enjoyed our day. These gals were top notch.  — Guests of Poinciana Treetop

Wonderful, Relaxed, Chill Kind of Visit

We've been thinking of our trip these past few weeks, while we've been sheltering at home clear across the country. We had such a wonderful, relaxed, chill Key West kind of visit just before Christmas. In some ways, it probably prepared us for what followed. We do so appreciate the hospitality and great property. Hang in there. — Guests of Casablanca Too

Four Glorious Days

We just spent 4 glorious days in Southard Comfort! The house was magnificent! We got in late Sunday evening and were able to easily get the keys and go to the house! The lights were on welcoming us when we arrived after 10 PM! I was beyond impressed with the cleanliness of the house and all of the decor! My husband, adult daughters and I loved relaxing in and around the pool! You can tell this home is loved by its owners! It is close to the marina where we hopped on a boat and ate at Sunset Key for lunch and did a sunset cruise another evening. It is also walking distance to Duval Street, Pepe’s Cafe, Date and Thyme, Five Brothers Market, and our new favorite restaurant, Mangia Mangia! On our way out to return home, we were all sad and said we will definitely return! — Guests of Southard Comfort

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. — Guests of Fair Winds at the Foundry

I Have Never Seen a House More Clean

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 Lux

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

Book Your Key West Vacation

We share these guests' comments with lots of pride and the only thing that could make us feel any better is to hear from you! Come on down for your most magical Key West vacation.  We'll make your stay so enjoyable your visits will soon become a tradition.