Cypress House Hotel Archives - Page 16 of 90 - Historic Key West Inns

Cypress House Hotel

601 Caroline Street Key West, Florida 33040 USA  |  Telephone: 305-294-6969
4.85 - based on 891 reviews

Cypress House Hotel – Delightful, Intimate Residence

Our stay in the Cypress House Hotel coincidentally and unexpectedly took place during the Papa Look-Alike Contest weekend, and as such, the island and thus, the hotel, were rife with Hemingway doubles.

I mention this because Key West can be a bit rowdy and Cypress House is quite close to Key West’s nightlife. Despite its location, the sprawling estate still feels relatively private and, once you find yourself back at your room, you don’t get the sense that you’re in the middle of it all.

The staff were all kind and helpful and- despite checking in shortly before the front desk closed, Scott still took his time welcoming us and kindly gave us a tour of the premises, providing us with advice and tips for our stay.

We booked a room with a porch, which I’d certainly recommend if you can spare the extra expense. While any Floridian or return traveler knows that the weather is seldom pleasant outside of the winter, nothing quite beats enjoying a nightcap or breakfast on your porch, surrounded by the garden perfume of jasmine, plumeria, gardenia and sea air.

The premises were well-maintained, the room spotless, and a positive experience overall. The sole opportunity for improvement I noticed was the breakfast- perhaps opting for fresher items would have augmented the experience.

Thank you for the experience; I’m looking forward to my next stay.

By: on August 1, 2016
Hotel Reviewed: Cypress House Hotel

5 / 5

Cypress House Hotel – Great Choice For Anniversary

My husband and I stayed at the Cypress House Hotel for our fifth wedding anniversary. I had mentioned it offhand when I booked and when we arrived there was a bottle of champagne waiting. The room was also large and spacious and the hotel amenities like the breakfast and drinks by the pool in the evening are a nice addition. The location was perfect for our first time in Key West, walking distance to everything we did but far enough off Duval that you felt like it was a quiet place to for a break from the busier areas. We loved it and would recommend it to anyone looking to stay in Key West!

By: on July 25, 2016
Hotel Reviewed: Cypress House Hotel

5 / 5

Cypress House Hotel – Best Spot So Far

We’ve been to Key West 6 times in the past 2 years and this has been our favourite place to stay. The location is great, close to Smokin Tunas (our favourite place for live music) and the Historic Seaport as well.

Scott on check in was amazing and the happy hours were great. The coffee was great and the breakfast above normal continental style.

We spent some time in the pool which was well maintained.

Our room had a beautiful porch and was probably my favourite spot to hang out and watch people walk by.

Highly recommend to anyone looking for old town Key West with all the modern conveniences.

By: on July 25, 2016
Hotel Reviewed: Cypress House Hotel

5 / 5

Cypress House Hotel – We Love Cypress House!

We just returned from our second stay at the Cypress House Hotel in Key West. Melissa at the front desk remembered us from our first stay and made us feel very welcome. She was so helpful, giving us tips on tours, and local sights. Jacob made our room up quickly since we arrived early. The staff have us a lovely gift of champagne since we were celebrating my husband’s birthday. The Cypress House is in the ideal location, has beautiful rooms and grounds. We brought friends to stay at the Cypress House Hotel and we all look forward to visiting again!

Thank you! Ericka Tannenbaum


By: on July 18, 2016
Hotel Reviewed: Cypress House Hotel

5 / 5

Cypress House Hotel – Pleasant Stay At Key West

We stayed from 7/9-12/16. Overall we had a very pleasant stay.


  • Close to the hustling bustling Duval Street(1min walk).
  • Renovated interior.
  • Spacious room
  • Delicious breakfast and afternoon cocktail/snacks.
  • Kind staff


  • No valet parking. Need to walk about 5 min to the public parking spot.
  • Since it is a historic building, there are no elevators. Highest floor is 3.
  • Air conditioning sound is loud.
By: on July 18, 2016
Hotel Reviewed: Cypress House Hotel

4 / 5

Cypress House Hotel – Above And Beyond

We did not know what to expect, as with all other vacations you book a place sight unseen and hope for the best. When we arrived Dennis was so kind in helping us with parking and showed us to our room. Without even asking he told us about several places to eat and enjoy the area. You have a great man who truly loves his job and meeting new people.

Every morning was very nice with breakfast and coffee. The afternoon lime time was so relaxing from days of fishing and sailing and exploring the area.

We were told by your staff to go to the Raw Bar up the street and that they would cook the fish we caught and they were right, it was amazing!

Our room was on the first floor with a private balcony that was amazing. I would love to know where you get the shampoo and body wash as it was amazing!

We were able to enjoy the quiet street and the most amazing access to Duval Street and all its attractions.

We are looking forward to coming again.

Thank you so much for making our first trip to Key West memories we will treasure forever. We have told all of our friends about your place and we are sure that there will be a group of us coming down!

Tammy & Rick

By: on July 18, 2016
Hotel Reviewed: Cypress House Hotel

5 / 5

Great Anniversary Trip Made Extra Special By Our Stay At The Cypress House Hotel

We celebrated our 33rd wedding anniversary at the Cypress House Hotel. The staff was great Melissa, Scott, Dennis and Jacob.  Melissa was especially welcoming and helpful with everything.  They all give it a personal touch and feel.  Whatever you needed they had.  It is a great location.  Short walk to all the old downtown spots on Duval street, Mallory Square and many others.

Then when you enter the hotel it is all peace and quiet.  We rented bicycles 2 days during our stay.  The rental shop was just 2 blocks away and really easy to rent and return.  The liming hour in the evening was perfect segway to coming in from the day’s adventure, have a great and different cocktail and snack each day before getting ready to go out that night.  Breakfast was great too.  The buildings are historic and updated and very clean.  We would have a hard time staying anywhere else on our next trip to Key West.

By: on July 13, 2016
Hotel Reviewed: Cypress House Hotel

5 / 5

Cypress House Hotel – Great Place To Stay

Rooms were beautiful, location is great. Enjoyed the small touches like 4:30 liming every evening and breakfast offerings in the mornings included in our stay. Staff was incredible.

By: on July 11, 2016
Hotel Reviewed: Cypress House Hotel

5 / 5

Cypress House Hotel – Most Amazing Place!

My husband and I went for his birthday and we couldn’t have been happier with the location, room, atmosphere, staff, breakfast, etc. Scott was amazingly helpful as was Melissa. I almost don’t want to tell you just how great it was for fear it will never be available to rent again! Best bed and pillows ever! Largest shower I have ever seen, great black out drapes for the early sun! Pool was quaint, patio was private, spiral staircase to our room was from a fairy tale! I love our room! Maybe we will try every room and decide which is best!

By: on July 9, 2016
Hotel Reviewed: Cypress House Hotel

5 / 5

Cypress House Hotel – Great Place

If you are thinking of staying in old town you cannot find a better, cleaner place to stay. The staff goes out of there way to make your stay great. Great staff!!! Pool is nice, good snacks too.

By: on July 8, 2016
Hotel Reviewed: Cypress House Hotel

5 / 5