My Hotel Was A Dump. Here’s Why I Booked Another Stay There

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In the fall of 2008, my friend and I went to Key West for an extended “girls’ weekend.” We stayed at Cypress House, a bed & breakfast on the corner of Caroline and Simonton, for 3 nights that October.

Back in 2008, I blogged, but only diary-style. I was not a travel blogger (Joe and I didn’t start YMMV until 2017), and my description and photos of Cypress House really prove that point ;-). Here’s that very blog post, in all its glory:

We finally got to Key West around 4:30 pm and found our bed and breakfast, Cypress House. The staff was friendly and the place was clean but the room was more than a little run down – most of the furniture was antique, or at least old, but it was nicked and scratched and really needed to be refinished. And the carpet, a 6′ square place carpet, was FILTHY. Besides being worn, the white areas had turned gray – that’s how dirty it was. It was just gross and not something I would walk barefoot on. The bathroom was across the hall – something of an inconvenience but we knew about that ahead of time and it was something we agreed we could deal with – however the lack of air conditioning in the bathroom was not expected. It’s still REALLY hot and humid in Key West (and practically all of Florida) in October, and a bathroom with no air conditioning was…not fun. At all.

We weren’t going to sweat (get it?) the small stuff though – it fit our priorities (clean [minus THAT RUG], not mondo expensive, 2 beds and high speed internet access) and as inns built in 1888 went, it was fine. And the 2 resident Schipperkes, Ben and Gabi, were ADORABLE!

Street view of Cypress House:

The Front Porch:

View of our room. It was L-shaped and didn’t look bad from a distance but it doesn’t take much to see all the nicks and scuffs on the furniture in the foreground. Note the bathroom towels hanging from the back of the door. And THAT RUG was just gross.

The Bathroom: Nothing fancy, and certainly without A/C (in 90 degrees and 99% humidity), but clean.

By the time we finished unpacking, it was Happy Hour at the B&B. Happy Hour ran from 6p to 7p and I have to admit it was THE BEST Happy Hour at any hotel or B&B I’ve ever visited. They had chips and salsa, cheese and crackers, crudité fruit and veggies and I can’t remember what else. And the booze – THE BOOZE! – dark rum, light rum, scotch, whiskey, you name it! All for free! Not that either of us are big drinkers by ANY sense of the imagination, but as someone who has been a guest in several B&Bs in her time, all of that to be complimentary, as part of Happy Hour, is VERY impressive!

Backyard/lounge/pool area where they do Happy Hour

We woke up on Friday at 9 am and enjoyed the breakfast buffet – there were all different kinds of cereals, fruits, breads and pastries to enjoy, along with coffee and a variety of teas.

Breakfast buffet at Cypress House (Modern-day note: My apologies for the coloring – the foreground is OK but I couldn’t get the background to be any less yellow):

So it appeared my impressions of Cypress House in 2008 were:

• Friendly
• Generally clean
• The dogs (I had COMPLETELY forgotten about the dogs!)
• Beat up furniture
• Awesome Happy Hour
• No air conditioning in the bathroom
• THAT RUG

Cypress House apparently changed hands a few years later – here are some photos on Oyster. The rooms looked nicer under the new ownership, but seriously, I think between the memories of THAT RUG, on top of the bathroom with no A/C, that I was grossed out enough where we never stayed there again.

Until now.

Fast forward to 2021 and guess what? IHG purchased Cypress House and 5 other properties on Key West in 2019. Now re-named Kimpton Ridley House, Cypress House was the last of the properties to undergo a multimillion-dollar renovation and was scheduled to re-open in mid-March. Joe discovered that IHG rewards are the best points to book a hotel in Key West, so he asked what I thought about staying at what was formerly known as Cypress House for our trip to Key West in April.

I was admittedly hesitant because even though it had been over a dozen years, I still just COULD NOT get THAT RUG and bathroom out of my head. I figured the rug would be long gone, and Joe promised me that as a Kimpton property, they would definitely no longer have unattached bathrooms without air conditioning LOLOL. So I said yes.

Here’s his review of the former Cypress House, now known as the Kimpton Ridley House.

Coincidentally enough, the guy who was manning the check-in when we arrived had worked at Cypress House when I had stayed there in 2008. His exact words were, “Yeah, it needed some work back then.”

Gee, ya think? LOLOL!

Anyway, you can still see the familiarity here and there (hello, slap on a coat of paint, and still use the same hardware on those kitchen cabinets much? LOL!):

But yeah, it’s changed a little. 😉

Feature Photo: Very Quiet / flickr

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This post first appeared on Your Mileage May Vary