Cypress House Hotel

601 Caroline Street Key West, Florida 33040 USA  |  Telephone: 800-549-4430
4.81 - based on 287 reviews

WOW!  Absolutely beautiful.  We were actually staying at a facility for a couple of days to celebrate our 25th anniversary.  Through our walk-about in town, we passed by the Cypress House and requested to view a room; immediately decided to stay in Key West a 3rd night… HERE.  WOW, bigger than our own bedroom and bathroom back home.  Can we move in?

Scott was very courteous and attentive to our needs, and such an amusing gentleman.  We hadn’t expected accommodations with happy hour and breakfast so this was absolutely over-the-top.  Absolutely love the mix of modern & antique decor in a historic home; you made it work!  Although we were traveling without our children, we’ve never thought of accommodations for adults only.  No wonder it was quite serene.  The atmosphere with the pool surrounded by tropical trees/plants made it all the more enjoyable! Location, Location, Location… perfect place to be with easy foot/car access to everything we wanted to do or needed.     And thank you for allowing me a small space in the kitchen to package our fresh catch from a fishing excursion.  Looking forward to returning to celebrate another anniversary.

By: on August 8, 2014
Hotel Reviewed: Cypress House Hotel

5 / 5


Thank you….I am now a judge during the Hemingway Days Festival. This Fest is a very lively group. The island lights up. I won in 2002 and have stayed at the Cypress since the win. There is  a lot of action during our stay. I like the closeness to our activities. My thing would be the breakfast! A continental style works for most of us. Not  a lot of early risers during this festival but never the less, some of us roll out. The kitchen works great both inside and out. I have suggested to the last two winners that they join us at  the Cypress. The Papas have found a home and appreciate what the Cypress does for us.  The Wednesday morning gathering gives all contestants a chance to schmooze with the judges and view the auction items that start on the first round on Thursday.

The Cypress house provides a great tropical setting for this desert rat. I would suggest that since we have heat in Phoenix during the same time frame that a  simple aerator system in the pool would work great and pull the temperatures of the water to lower degrees…I am not sure how a misting system would work but it would be worth an experiment. Thank you for the trust of your house cleaning people…we set our change and cash out ….it is still there with a very tidy room. The shower was always clean and great. I might encourage you to do what they do on cruise ships….which is optional…perhaps an envelope for their tip could be provided…   I walked Duval on the Monday following    an attempt to connect with an art gallery that would carry my whimsical  art  and our Hemingway experience while on the Island. I will  continue to seek my  place until I am successful…leads will be deeply appreciated…….of course this would be yet another reason to return to your wonderful island………..thanks again for the  adventure….

Ron Thomas, Papa 2k2

By: on August 7, 2014
Hotel Reviewed: Cypress House Hotel

5 / 5


This was our second time staying at the Cypress House and it was stellar!  We arrived just after 10pm and the gentleman was just about to leave for the night but he speedily checked us in.  We stayed Thursday-Sunday in a standard queen room.  Very clean room with a spacious bathroom, and all updated decor and fixtures.  We enjoyed the pool during happy hour and the appetizers offered were fabulous!  The staff is always so friendly and it feels like staying with friends rather than in a hotel.  The best part is the central location to everything in Key West.  My boyfriend surprised me with an engagement ring on this trip so it was extra memorable!  We are looking forward to another great trip to Key West and stay at the Cypress House.  Thanks!

By: on August 6, 2014
Hotel Reviewed: Cypress House Hotel

5 / 5


My husband and I stayed at the Cypress House for the first time over the latter part of July and it was wonderful! We were with a large group for a bday party and the accommodations were incredible. The rooms are so clean and large and very comfortable. The entire staff was amazing, especially Dennis! We will definitely come back and stay again.

By: on August 5, 2014
Hotel Reviewed: Cypress House Hotel

5 / 5


I was extremely impressed with our 2 night stay at the Cypress House. The staff was friendly and seemed to want to go out of their way to please their guests. This was my first stay at a b & b and I can’t imagine staying at a big resort while in the keys after my experience at the Cypress House.

The location was the selling point since we didn’t want to drive around. It was close enough to the Duval and shopping areas for convenience, yet far enough for peace.

The breakfast and happy hour surpassed my expectations. The complementary flavored water and coffee throughout the day and evening was a nice little bonus too.

When I return to Key West, I will stay no where else!!

By: on August 5, 2014
Hotel Reviewed: Cypress House Hotel

5 / 5


From the moment we entered the Cypress House we were greeted warmly by Chris and Kelly. We had a small issue because we were told on the phone that we would be receiving the “Third Night’s a Charm” discount, but hadn’t gotten confirmation yet. After explaining the situation to Chris, he promptly adjusted our rate. He also upgraded our room and gave us the “Library” room we fell in love with on the website. The room was gorgeous, historic, clean, and cold (perfect escape from the heat and humidity) — all the things we wanted and more! Every moment we were at the Cypress House was pure relaxation. Both the breakfast buffet and Liming Hour were wonderful additions that made our trip even better. Our one and only situation was that on our second night, my boyfriend’s birthday, the ceiling began leaking – a little at first, then pretty badly. We called Alexander at the front desk who moved us to a new room. We were quite upset with the second room because it definitely wasn’t nearly as nice as our current one and it was very far. It would be extremely taxing to move all of our stuff down the block in the middle of the night for one night. Alexander made some adjustments and was able to move us to a closer room, explaining the situation and the “adult water party” that occurred above us that was being dealt with accordingly. We understood -What could you do in that situation? The next morning, when we moved to back to our original room, we already had a new receipt displaying a reduced rate for our inconvenience. Overall, despite minor setbacks, we had a wonderful stay at the Cypress House. It had everything we were looking for in a getaway weekend – relaxation, history, hospitality, and a little unexpected “Adult Only” Key West craziness. We would definitely return and recommend this place to others!

By: on August 5, 2014
Hotel Reviewed: Cypress House Hotel

4 / 5


Cypress House was a wonderful place to spend my first trip to Key West with my wife and friends. It offered all you can ask for in a home away from home. The entire staff was excellent and very accommodating, especially Dennis. From checking in to checking out it was a smooth process. Our rooms were kept nice and clean as well. The location was great! It was walking distance to everything.

I would recommend Cypress House to anyone. Make sure you get to Blue Heaven. The food was awesome!

By: on August 5, 2014
Hotel Reviewed: Cypress House Hotel

4 / 5


The Cypress House is perfect for anyone that wants to be close to many of Key West’s best attractions while staying at a quiet, private location.  The rooms were modern & comfortable, the staff was amazing, and the location could not be beat. The breakfast was awesome and the free happy hour was the perfect way to end the day and start the evening.  This was my first stay at the Cypress House and will not be my last.  Stay here now!

By: on August 5, 2014
Hotel Reviewed: Cypress House Hotel

5 / 5


From check-in to check-out, everything was perfect. Location of the hotel is outstanding and couldn’t be closer to Duval while still the privacy and seclusion of a quiet weekend getaway. The staff is personable and friendly with good suggestions on anything you may want to do.  Our room was clean and had the perfect Key West decor and we couldn’t have enjoyed ourselves any more!

By: on August 4, 2014
Hotel Reviewed: Cypress House Hotel

5 / 5


Recently took a short trip to Key West from Islamorada for a few days of relaxation from work and we picked the right place! Beautiful hotel with a great location, friendly staff, clean rooms and grounds, and fun pool!  Walking distance to so many fun places and just a short bike ride to the Southernmost Point. Can’t wait to return and visit my favorite restaurant Santiago Bodegas in September!  The only thing that would make this place perfect would be some type of shuttle to the parking ramp. Thanks for the great hospitality!

By: on August 4, 2014
Hotel Reviewed: Cypress House Hotel

5 / 5