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Historic Hideaways Choose from private and historic Key West Vacation Rental homes with private pools, a cozy cottage, vacation houses, condominiums or townhomes with a shared pool. Each of the unique and charming Key West Vacation Rentals on our website has a detailed description, along with great interior and exterior photos, a list of amenities, and a map location. Whether you're looking for an oceanfront rental, an Old Town vacation rental or a house in one of the residential areas of the island like Casa Marina, we have you covered.
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Historic Hideaways LLC has been in the vacation home business in Key West for over 25 years. We offer quality Key West vacation home rentals that include villas, condos, townhomes, and private rental homes. We specialize in Weekly as well as Monthly and Seasonal Key West Vacation Rentals. All of our vacation home properties are located on the island of Key West itself.most in the Old Town Historic District.
Vacation rentals in Key West are perfect places to experience this special island. Every Key West rental has its own distinct charm. As one of Key West's first property management companies, we represent some of the best rentals in Key West's diverse communities. Many of our historic homes, villas, and condos come complete with private pools and beautiful outdoor areas that are great for singles, couples and families alike. We work closely with our guests to ensure that you receive personal service throughout your Key West Vacation.
Historic Hideaways offers some of the most comfortable and well-appointed nightly and weekly vacation rentals in Key West, many with private pools and lush Keys-style landscaping. Most of our weekly vacation rentals have a 5 - 7 night minimum during season, and a 2 - 3 night minimum (excluding Truman Annex) during the off season.
Key West Monthly and Seasonal Rentals are the perfect option for an extended stay in Paradise. Historic Hideaways offers numerous options to make your stay hassle-free and filled with the best that Key West and the Florida Keys have to offer. Monthly/Seasonal Rentals have 30 day minimums. Except for Jan - March, they are not restricted to calendar months.
Reviews (10)
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Hunter Pierce
Jan 26, 2022
Have used Historic Hideaways for the last 5 years. I've enjoyed working with them, their rentals are clean and comfortable. Booking experience has been easy and their customer service is top notch. Will continue to use Historic Hideaways every year we come to Key West.
Julie D.
May 12, 2021
Second year staying in this house. We love it there. Clean, comfortable, the pool and deck amazing. Close to everything, but still secluded, and private. Tim is always great, and answers any questions we have. Will definitely rent again
Cherijanie Campbell
Apr 20, 2021
Rose's Treehouse was perfect for a short birthday getaway! Absolutely beautiful with both a front and back porch. Another great feature.we were steps from Duval. Historic Hideaways knocked it out of the park again! Thanks Tim :
Nancy Byard
Dec 29, 2020
"Admirals Lane is our favorite rental home! This was our second stay here and we were not disappointed. The house is beautifully appointed and spotless and we feel like this is our home away from home. Tim from the Management Team is amazing to work with. We had a minor issue with the dishwasher and he had the maintenance crew there within the hour! My family and I are planning our next trip in the near future and we can't wait!"
Jill Augustine
Dec 14, 2020
Our stay at Havana Hideaway was perfect! The condo was clean, spacious, quiet, and relaxing. We had every amenity we needed from yoga mats and beach chairs to washer/dryer, dishes, and towels. The location was absolutely amazing! We were 3 minutes' walk from Mallory Square, 10 minutes' walk from Blue Heaven, 2 minutes to Duval Street, and right on the water.

We could walk along the pier or along beautiful Emma Street. The neighborhood was beautiful and most importantly it was safe. The salt water pool was clean, large, and had plenty of seating any time of day. It was a great area to basque in the sun or watch a sunset! We will definitely be recommending this location to friends and family! Tim was available any time of day to answer our questions. Thank you Historic Hideaways! We hope to be back soon!
Betty Hacala
Nov 24, 2020
Our first vacation since the pandemic and I just had to review this company and the owner of HH - I left a carry-on bag with valuables when we checked out of our rental and Historic Hideways ( Bill ) was so professional and caring. He not only located my bag but took the time to have it fedex'ed to me when I arrived home. Forever grateful for his prompt response and compassion when I was frantic! Thank you Bill and Historic Hideaways!
Eric Pierce
Dec 02, 2015
Met Tim upon our arrival - he greeted us warmly and allowed us to store our luggage in the office until the house was ready for us. The unit was available about an hour early which was great. Only a few blocks from the Seaport and Duval, we found it to be in a perfect location. It's far enough away from the noise, but close enough that no car was necessary.

The house itself is wonderful with lots of character. The house was clean upon our arrival. Suficient cleaning supplies helped us keep it that way. We visited in July, so the pool saw plenty of use (plenty of towels). Another reviewer wrote that he wished there were cold beers in the fridge - he is right; that can be arranged (and we did)! We were a party of 8 adults so the the twin bedrooms were not ideal, but we knew what we were getting when we reserved. But the rest of the house more than made up for it. By all accounts, the house was perfect. We will all be back.
Karen Kincaid
May 25, 2014
Rose Cottage rented through Historic Hideaways. My husband and I loved this home, it was beautiful and close to everything so walking wasn't a problem. It was so nice to come home after a day seeing the sights and relax on the deck surrounded by wonderful landscaping. Tim at Historic Hideaways was extremely helpful making our rental, check-in and check-out smooth and efficient.
Z. Charnas
Jan 05, 2014
The home was lovely--great location, gorgeous pool, and backyard like paradise! Most importantly, dog-friendly although the local cat didn't seem aware of that. The kitchen stove was a little odd for me to use. It had to be lit as it uses propane. I left the lighting to my husband as I am not fond of igniting stove/fires. The one drawback to the house is that for the heat of late May or summer, the A/C cannot handle the back bedroom or bathroom.

It got quite hot a couple of days. It was warm most other days, but we like the warm weather. This is the only major issue we had with the home. We love the one level living and the porch was perfect for dining. (There is even a second patio that we didn't use.) There were a couple of issues when we first got there, e.g., the hot water didn't work in the outside shower. We told Tim, of Historic Hideaways, and it was fixed immediately.
Rebecca Cliche
Jan 02, 2014
The Ann Street Garden unit was great. The location could not be beat, and the home itself was private, quaint, quiet, and clean. We requested the late check-in service and it went very smoothly. The outside light and a couple of lights inside were left on for our arrival. We thought that was a nice touch. We enjoyed the private patio, the separate bedroom, and cute kitchen area.

They have just about everything stocked that you could need; hairdryers, iron, all the kitchen gadgets to make a fun drink or a meal too. I'll reiterate that the location can not be beat. Literally around the corner from Upper Duval, but in a very peaceful location. We really enjoyed our stay at the Ann Street Gardens and hope to make a return trip much sooner than later!