Historic Key West Vacation Rentals offers luxury historic vacation rental homes in Key West Florida. 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.

How are we doing? Our guests say it best. Read what our guests are saying about our premier vacation rentals and our services.

Chick-a-Pea Cottage - Nightly Rental 

"The house was so perfect, had so much Key West character, was clean and the pool + patio such an added bonus! The best location to everything! Rental company was amazing, we accidentally locked ourselves out of the house, and Susan came right over to let us in within 10 min! They checked on us throughout our stay, and anything that came up they were very responsive. We had the perfect stay, and plan to stay here for many more trips!!!"

Sea Conch - Nightly Rental

Amazing property


Sea Conch is an amazing property. Everything on the listing is exactly as it is in person. The house was very clean and the pool area very nice. I was able to order groceries online from Publix and get them delivered the day of our arrival along with bikes for the week. The location is awesome! We will definitely be back the next time we come to Key West!!

Martha Truman Suite - Nightly Rental

My husband and I stayed here for a week for our anniversary. The condo was spotless. Very nice furniture inside and out! Everything seemed updated and there were plenty of towels, etc for the week. The kitchen was very organized with very nice dishes and appliances. We had a problem with our washing machine and they were at our place within 15 min to look at. it. It couldn't be fixed that day, so they allowed us to use the machine downstairs at the empty condo. They were very attentive and helpful. We also encountered a hurricane (kind of) and they were out to take care of the outside furniture and made sure we had flashlights. They returned the next day to set all the deck furniture back up. The pool is very private and beautiful and we enjoyed reading there every am. Everything was well taken care of and we would stay there again! Location was the best! We walked everywhere! 

Martha Truman Suite - Nightly Rental 

Cute and Convenient Key West Suite

This was the perfect rental for a long weekend getaway. The suite was nicely decorated and up to date. Loved the dipping pool and back deck to relax! A short walk to Duval street shopping and restaurants - Key West Cuban Coffee is just down the street and is amazing! Rented bikes and booked an excursion through the concierge, who was incredibly sweet and helpful. Had a wonderful stay and hope to be back!
Villa Azul - Monthly Rental

There were three of us working from home in this house. It was perfect for all of us. The rooms were the perfect size. The outdoor space is an amazing oasis for when you have downtown. We really enjoyed our stay and the location was perfect.

Villa Luxe - Nightly Rental

We had a wonderful stay at the Villa Luxe! It was a beautiful property that provided just the relaxation we needed! The management staff is professional and available for any needs. The location was perfect for us! A short walk to anywhere we wanted to be! There is a convenience store located a few steps away which was so nice for a quick snack or more drinks! The covered porch allowed us all to still sit outside and enjoy the beautiful landscape, even in the rain! We will definitely recommend to family and friends!

Southard Comfort

From the time we pulled in the driveway, Southard Comfort was inviting, quaint and more than we expected. First, having a parking space in key west is a blessing! The home met every one of our needs and more. The pool was tranquil and welcomed us home each day after exploring Key West. The beds were comfortable and there was tons of storage. The roosters crowing at 5am just added to the Key West vibe. The kitchen was well stocked and the AC and fans kept the house super comfortable. Don’t miss this little oasis!

Casablanca - Nightly Rental

Another wonderful experience in Key West! The property was lovely, and you can't beat your own private pool. There are not many 1-bedroom vacation rentals with a private pool on the island, and this one is top notch! The staff at Historic KW Rentals are professional and accommodating

Bess Truman Suite - Nightly Rental

We really enjoyed our stay. The unit was perfect, and immaculate- your cleaning crew is amazing. (We have rentals in OC Maryland and always have issues with the cleaning company-so that was the first thing I noticed).
You and your team were amazing with everything, kept us informed and knowing exactly what to expect.
We truly appreciate your hospitality and will be seeking out HKWVR for our next trip.  

Tropical Dream - Monthly Rental

We stayed for one marvelous month and wish we could have stayed longer. The home was perfectly situated in the heart of Old Town. It is FULLY equipped with everything you could possibly need and want. From kitchen supplies to bed linens and BBQ tools - everything was perfect!
As far as the rental company, I can’t say enough good things about these ladies! They are marvelous! Our BBQ was not working one day, so they gave us a gift card to the lovely restaurant down the street to enjoy while the repair was underway.
If you’re on the fence don’t be! You will not be disappointed.
For reference, this glowing review is coming from two very picky frequent travelers who only write reviews in response to terrible experiences. That's how much we enjoyed our time at Tropical Dream.
Perfect home and perfect service! 10 stars

Maisons de Luxe - Nightly Group Rental

“The biggest plus was the constant communication and quick repackages to questions. The location and house are awesome. But the people I dealt with were exceptional.”

Southard Comfort - Nightly Rental

The best we have rented so far! Our host was amazing, they gave us local recommendations and were available for anything we needed! The place was awesome. The most beautiful decor and comfortable rooms. Very easy access to everything, we walked everywhere we went! Would definitely recommend to all of our friends! Thank you for a wonderful and memorable stay!

Maisons de Luxe - Nightly Group Rental

5 stars:
We fell in love with Maisons de Luxe when we saw the pictures on the Historic Key West Vacation Rentals website, so much so that we planned our destination wedding around its availability.  From the very beginning, Denise and Cindy were friendly, professional and bent over backwards to make sure we were well taken care of.  Cindy was extremely accommodating and very responsive to all our needs.  The property itself exceeded our expectations.  We had 6 adults and 2 children in the main house and 2 adults in the petite and still had plenty of space.  It was beautifully furnished, clean and conveniently located.  The backyard was a huge hit with our group, we spent hours every evening in the pool relaxing, grilling on the bbq and enjoying local food and drinks.  We definitely plan to rent from HKWVR again in the future as our family is already feeling “homesick” for Maisons de Luxe.

Rooster Conch - Nightly Rental

“Excellent place to stay, very clean and private. The hosts were excellent in their communication, your 2 blocks from Duval street. We loved it!”

Queen Conch - Nightly Rental

Absolutely amazing! There were 12 of us in our group but the house could have comfortably slept 14. Location is perfect, just a short walk from Duval St. The house was spacious and clean. The pool was probably our favorite part. There are lots of trees and plants surrounding the pool so it gives you a lot of privacy. I would definitely stay here again! The staff at Historic Key West Vacation Rentals was so helpful and attentive starting the first day after booking and continuing through the last day of the trip. Such a wonderful experience!

Maisons de Luxe - Nightly Group Rental

Based on the pictures and reviews, we had high expectations for this property. We were not disappointed! The house is beautiful, perfect Key West style, great layout, great size and very clean. Couldn’t have been better, first time, definitely not the last time. Miss it already!  

Sea Conch - Nightly Rental

The Sea Conch home is a lovely place to stay. The furnishings are very modern, space has everything a traveler could ask for and the neighborhood and location were perfect! We would (and will!) definitely stay there again on our next trip to Key West!!

Sea Conch - Nightly Rental

This property was everything we were looking for and more. The hosts were very friendly and helpful, everything was clean and in great condition, and the pool was perfect for our group. The location is almost impossible to beat. The only time we drove was to go to the grocery store or beach. Everything is walkable. I will definitely want to stay here in the future and recommend it to anyone I know going to key west.

Bohemian House - Monthly Rental

The property is in the perfect spot; close enough (2/3 blocks) to Duval, but still far enough away where street traffic and noise are not a factor. House was very well appointed with everything you need for entertaining. Bedding was comfortable and well kept. Property manager was very responsive throughout entire trip.

Bohemian House - Monthly Rental

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!

Seas The Day! - Weekly Rental: 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!!


Cloud 9 - Nightly Rental 3 Bedrooms 3 Bath Sleeps 7

"During these trying times that we are living in, we needed a safe getaway and that's exactly what we got. The minute we walked through those gates, we felt like we were transported to our own little island. The pool, decor and location of this oasis, was bar none. Cloud ☁️ 9 was fully equipped with everything you would have in your own home. The staff was wonderful, accommodating and very professional. We have all intentions of returning next year. This trip is definitely going on the ones to remember. Thank you for the memories!"

Poinciana Treetop - Nightly Rental

"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. " 

Casablanca Too - Nightly Rental

"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." 

Southard Comfort - Nightly Rental

“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 10PM! 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!”


Maisons de Luxe - Nightly Group Rental

""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."

Fair Winds at the Foundry - Weekly Rental

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."

Villa Luxe - Nightly Rental

"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."

Grand Maison - Nightly Rental

"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."

Villa Luxe - Nightly Rental

"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."

Fair Winds at the Foundry - Weekly Rental

"We cannot say enough about FairWinds 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!"

Poinciana Garden - Nightly Rental

"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

Bess Truman Suite - Nightly Rental

"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.

Poinciana Garden - Nightly Rental

"Historic Key West Staff was courteous and friendly. If i had a question they were able to help. Poinciana Garden was immaculately clean and furnished. It even had its own parking spot which is a great thing in Key West. Only a couple of blocks from everything" - Kevin L.

LITTLE TRUMAN COTTAGE - Brand New Cottage w/ Pool

..."exceeded my expectations!! Do not look any further than this place-centrally located with a beautiful pool to relax in. This place has it all, and I can’t wait to stay here again!"    Clara, Tonawanda, NY

 GRAND MAISON~ Luxury Home On Duval w/ Pvt Pool!

"Beautiful home, great location! On Duvall so very easy to walk to places, but it’s on the 'quieter' end so you get to enjoy your sleep. Back yard area with pool was a great hangout and relaxing spot. The check in office went above and beyond anything we needed. If I stay again this is where I’d stay!!"    Kindel, Ocala, FL

LITTLE TRUMAN COTTAGE - Brand New Cottage w/ Pool

"We very much enjoyed our stay at the cottage. It was beautiful and in a PERFECT location. Far enough down Duval to feel quiet, but still close to everything. Fantastic places all within walking and biking distance. We would definitely stay here again!"    Wendy, Raleigh, NC

Harry Truman Suite - Luxury Suite Steps To Duval!

"My friends and I stayed here for a birthday weekend! It easily accommodated the 5 of us! Super easy to get to the bars, the place was super clean and overall a great place to stay!"    Marissa, Coconut Creek, FL

LITTLE TRUMAN COTTAGE - Brand New Cottage w/ Pool "Such an amazing cute and comfortable place! Was walking distance to everything. The pool was a great addition. Would recommend this place to anyone!! Don’t think twice. And the rental company was so nice and helpful!!"
Harry Truman Suite - Nightly Rental

"Just celebrated New Year's Eve in Key West and was fortunate to stay in the Harry Suite of the Truman Suites. Beautiful accommodations in a great location!"

Villa Luxe - Nightly Rental

“This location is a hidden gem. The Privacy off being located close to Duval , but you actually is unbelievable. This place is been extremely tastefully done. The value for the money is easily justified. Considering stayed many times at local high end hotels and this is much more intimate. Great job to the owner. Loved the Sonos too I stayed with my family and having 3 separate suites made it more enjoyable. Family room layout and private pool created some relaxing time. Great place for 3 couples also. We will be back for sure. Staff at Historical Key West was excellent to deal with. From Concierge type service for restaurants (Cindy nailed it) to Susan at check in and followed up first night with assistance. Too Steve upon checkout. Enjoyed the friendliness.”  

Potter's Cottage - Nightly Rental

"Just came home from a wonderful first trip !! Loved the island ! Loved the house .... stayed at Potter's Cottage."














Cloud 9 - Nightly Rental

Our stay at Cloud 9 was a perfect experience from the booking, the accommodations, the beautiful pool, location to check out. The staff could not have been more accommodating. We loved the rental! 

Villa Luxe - Nightly Rental

We had a wonderful stay at the Villa Luxe! It was a beautiful property that provided just the relaxation we needed! The management staff is professional and available for any needs. The location was perfect for us! A short walk to anywhere we wanted to be! There is a convenience store located a few steps away which was so nice for a quick snack or more drinks! The covered porch allowed us all to still sit outside and enjoy the beautiful landscape, even in the rain! We will definitely recommend to family and friends!