History Meets Laid Back Luxury in Key West at the The Cypress House Historic Inn


cypress house historic inn Key West

The beautiful Cypress House Historic Inn in Key West dates back to the late 1800’s.

As I was searching for the perfect place for my husband and I to stay during our romantic Key West getaway I came across the Historic Key West Inns website and I knew I had found something special.  Historic Kewy Est Inns consists of a collection of 6 boutique hotels located on historic properties. All of them are in Old Town, close to  restaurants, attractions and nightlife.  We chose to stay the the Cypress House which consists of two Classic Bahamian Conch Style houses and one Grand Conch Mansion, all dating back to the late 1880’s.

Cypress House Conch House Key West

One of the Conch Houses that is part of the Cypress House Historic Key West Inn.

When calling to make the reservations I was really impressed by how friendly and helpful Mary, the sales manager was.  Upon arriving to Key West aboard the Key West express from for Myers I called her to let her know we would be there soon and she offered to pick us up on her Golf Cart and take us to the hotel because she was in the area.  As she drove for a couple of blocks to the hotel she told us about the area, the interesting history of the hotel and showed us a coconut she had painted herself as a welcome gift for a couple of newlyweds, we thought that was such a thoughtful and personal detail. We received a warm and friendly welcome from the front desk staff and immediately knew we had made right decision by choosing the Cypess House.

cypress house historic inn Key West

The rooms at the Cypress House in Key West where just the right size and the bed was very comfortable providing for a great night’s sleep.

As we where shown to a King room with a porch in the main house we felt like we where being transported back in time. The beautiful rustic mansion looks out into the street with it’s private porches and beautiful antique lamps. The rooms are beautifully decorated with a combination of contemporary comfort, antique furniture and modern day amenities.   The outdoor areas, while small are charming with lush tropical landscaping the give the Cypress House a real laid back Key West atmosphere.

margarita cypress house historic inn Key West

Complimentary Margarita at the Cypress House Historic Inn, Key West

Eager to go start enjoying everything Key West has to offer we set out to explore and loved how close the Cypress House was not only to Duval but also the the port, Mallory Square and to so many restaurants, museums and attractions.  We took advantage of the refreshments available throughout the day and relaxed on our front porch, people watching before joining the other guests at the evening ‘Liming At Cypress House – The Art of Doing Nothing’. At 5pm a nightly cocktail and light appetizers are served poolside, on that particular day there where Margaritas accompanied by delicious and hot pulled pork sandwiches.  This was the perfect afternoon snack just before heading out to enjoy the nightlife on Duval, just a couple of blocks away.

After a good night’s rest on the comfortable bed we enjoyed the complimentary breakfast and sipped our coffee and tea while sitting on our porch and taking in that deliciously relaxing Key West vibe before checking out.

cypress house historic inn Key West

Enjoying the porch in front of our room at the Cypress House.


Things We Loved About the Cypress House

  • Fantastic location on a quiet street just a short walk away from Duval and Mallory Square.
  • Free wireless internet
  • Free breakfast which includes fresh fruit, pastries, bread baked daily and a different egg frittata every day as well as a variety of cereals, yogurts, etc.
  • Water and refreshments are always available by the pool, which was great as we did a lot of walking and could cool off poolside or on our private porch overlooking the street while sipping delicious fresh lemonade.
  • Daily happy hour poolside with different cocktail every night and hot appetizers, the perfect time to mingle and get to meet other guests.
  • Warm and friendly staff and attentive service.
  • Comfortable beds and relaxing atmosphere.
  • The Cypress House is not only a historic landmark but it also has a very interesting history.It was the estate home of Richard Kemp an avid naturalist and fisherman. The Kemp’s Ridley sea turtle was named after him, having submitted the species for identification in 1880.
  • The Mojito Bar & Café, located inside the Lighthouse Court Hotel across the street from the Hemingway House has a happy hour where you can enjoy cocktails before you head out for dinner and it welcomes guests who are staying at any of the Historic Inns, including the Cypress House.
cypress house historic inn Key West

Breakfast by the pool at Cypress House Historic Inn Key West


Things to Consider

If you are thinking of staying at the Cypress House hotel there are some things you should take into account.

  • This is an adult only hotel that is best for couples.
  • The Cypress House is made up of a series of historic buildings that date back 120 years. Don’t expect electronic keys on the doors.
  • Parking options are limited. There are a few free public parking spaces in front of the hotel or you can leave your car at a municipal parking lot a couple of blocks away for a daily fee. For us this was not an issue since we arrived via the Key West Express and did not have a car that needed parking.
  • Some of the rooms are really close to the street, if you are a light sleeper take that into consideration when choosing a room. We where in a corner room just a few feet away from the intersection of two streets but the little noise that came from the street didn’t really bother us.  I can see this being a problem during high season and special events when people are walking back to their hotels at 2am in the morning after a few drinks.
  • If you will be doing a little work while on vacation, which should not be the case but I’m just saying this for those who are workaholics like me, some of the rooms don’t have a desk.  For me this actually turned out better as I ended up going out into the porch or to one of the tables in front of the pool and worked on my laptop outdoors, which was really nice.
  • The common areas are mostly outdoors which means no air conditioning. There is a really nice 40ft lap pool but space four lounging is limited.

Our stay at the Cypress House was really unforgettable, the staff was friendly and attentive and I loved staying in a historic building and getting a real Key West experience.

Visit the Historic Key West Inns website to learn more about their inns, like their Facebook page and follow them on twitter @KeyWestInns to stay up to date with their latest news and specials

This is part of a series of articles: Romantic Key West Getaway, you can read more articles in the series HERE. #KeyWestGetaway

Follow 365 Things to Do In Southwest Florida on Facebook for the best travel ideas, events and attractions for the whole family.


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  1. Wow what a pretty house! I would love to visit and relax by that pool and on the front porch – maybe one day 🙂 x

  2. we love B&B this one looks super nice and cozy

  3. wow I beautiful makes me want to come visit Key West one day will have to se how far it is from where I live

  4. This is so perfect, I have a race coming up down that way. If this is close enough maybe I can go relax there.

  5. Very secluded and romantic place for a getaway.

  6. Looks like a very comfortable stay you had there. I love the color of the house and what they did on the exterior front house.

  7. What a beautiful Inn to stay especially those newly weds. That is a very romantic place.

  8. The Mojito Bar & Café sounds like a great place to relax and unwind before dinner. I’d love to visit with my husband. Maybe for our 10 year anniversary.

  9. My stomach started to grumble upon seeing the croissant lol. Such a beautiful place, never been to Key West yet but been to a couple of cities in Florida.

  10. I love this type of place. I love staying at hotels or houses that have so much history to it and that old rustic elegant feel is something to admire. Gotta love that. We have stayed in some historic places before and we love the peacefulness, the calmness and that feeling of being in a house that has been around for years, make you feel kind of connected. I don’t know. Maybe it is just me being weird. LOL! Thanks for sharing your review. It gives us an idea where to stay and what to expect.

  11. This hotel reminds of me of St. Augustine bed-and-breakfast places. The buildings are rustic, but dainty.

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