Simonton Court Hotel Key West — Hotel in Key West

For the high price, I was a little disappointed. The room we stayed in was on the 3rd floor of the old mansion. The floor is -really- dusty on my feet (which are now black), I moved the ottoman and there was a square shaped patch of dust that is pretty thick (don't bother mopping if its that yellow bucket with the rag mop thing. All that does is push dirt around and never actually gets clean.) Also, there are no shower curtains, so not only does the water spray all over the floor, but there is a horrible draft that makes you shiver constantly while showering. Also the shower head is cheap motel quality, so it gets only spray/mist on you everywhere except for where you want it. Seriously, this room is $250+ a night and you couldn't invest under $50 for a better shower head. My fiancée tried washing in the tub, but that sprayed everywhere too. No wonder the chair next to the tub has water stains on it. Also the tub takes forever to drain. Like 30+ minutes. But at least the water was hot...unlike my parents room who had no hot water. There was also some orange/pink mildew under the shower step. There is no place to eat in the room if you like breakfast in-room (as in, no table). Outside, the building could use a paint job, its becoming run down looking instead of shabby-chic. The grounds have absolutely beautiful gardens, the pools are lovely. The windows need to be thicker, like...noise canceling. There is a theatre across the street and when it let out at 10pm you can hear -everything-; cheering, yelling, laughing, and the bar down the street It's very loud with just regular road noises. Oh yeah, and a lovely argument outside where a man shouted "leave! Just leave!" Prime entertainment. Luckily the heat has us feeling pretty beat, so we got some sleep. Pros: The staff is very friendly. The cats on property made me feel at home. They even came in to our room and had some snuggle time. We are pretty homesick and miss our own cats terribly so this helped soothe the ache. Staff, please take care of the cats! They are wonderful. They seemed well groomed, soft coats, loved people, so hopefully they do ok there. The included breakfast is nice, but mostly starch and some fruit. Loved the fresh squeezed orange juice.

Overall I gave it 3 out of 5 stars for lack of cleanliness and noise level. We ended up spending a lot of time in the room because we needed to cool off and we are both sick so I had a lot of time to...

Here is my sincere review after multiple stays. Simonton Court is one of my cherished oasis—a true last bastion of authentic Old Key West. Unfortunately the rising tide of homogenization and sterile modernity leaves this place as one of the few remaining places to be able to experience what made Key West such a lovely place. That being the beauty and delightful perfection of imperfection. So much of newer development in Key West (and everywhere) is fixated on drywall precision and an unattainable, sterile perfection reminiscent of operating rooms, devoid of soul and character. Key West was never about conformity or clinical precision; it was about freedom, uniqueness, and embracing the beautiful imperfection in everything and everyone.

Sadly As genuine Key West slowly fades into a memory, replaced by the artificial illusion of perfection, Simonton Court remains an enduring haven of beauty, nature, serenity, and timeless charm. Here, the historical buildings with authentic character abound, nestled within lush gardens and paver sidewalks—delightfully uneven and charmingly imperfect, echoing the spirit of a place that defies laboratory replication.

This is an outstanding resort. But it is not big box perfect. There is not a shiny stainless steel service elevator that can lift a city bus, there are stairs. Yes, you may have to go up old fashioned human powered stairs. The floors are not level. They are clean, but not level. These are 100+ year old buildings. Enjoy the slope. The light switches or plugs are in odd locations. It’s ok, these buildings were built before our precious electronics were even dreamed of. They work, but are not perfectly located exactly so many inches high and so many inches away from a door like we find predictably in new construction. These buildings weren’t built in a factory. So as long you don’t expect 21st century modern precision, you will be delightfully pleased. If you expect differently, you will be disappointed. Either way, it’s your choice.

Jonathan and the entire Simonton Court team, your commitment to preserving this rare and beautiful sanctuary is extraordinary. Thank you for providing an experience that celebrates life's wonderful imperfections...

Stayed here with my wife for our 1 year anniversary/late honeymoon.

I cannot say enough good things about this hotel. I would treat and consider it more like a resort.

The grounds - beautiful. Manicured, picturesque, romantic, private, quiet, peaceful.

The pools - unbelievable being able to go between different pools. When we were there, it was so easy to find a completely empty pool that my wife and I could relax at alone. Maybe someone heading to their room walks by, but it’s a very intimate setting and relaxing. Trust me if you’re looking for quiet relaxing time by the pool near Duval? You book here.

The room - we booked a Deluxe King and were upgraded to a Deluxe Cottage. The Cottage was very clean, very well air conditioned, and well serviced daily. I actually think they should take better photos of some of these cottages, because if I knew I’d have that shower, I’d have probably booked it. Two shower heads, no brainer. It could have been a smidge more private, but it’s not as if we had people looking in the slightest. We just could, if we wanted, sometimes see people at the pool. Not a problem at all cottages. Not even a problem.

The staff - very nice and attentive. Never a burden or interrupting. Just enough that you felt very well taken care of if you needed anything.

Perks - loved the bikes. Book through Simonton, get the bikes and taken them around for the day. Loved the fact that we were alerted as soon as we were able to check in. Loved that any questions were a text away and were taken care of quickly.

I will say, my wife and I thought this place was perfect. If we wanted party party party, this is probably not the place. It’s a relaxing atmosphere and peaceful. Could three couples enjoy themselves here drinking at a pool? Of course. But don’t expect a DJ with strobe lights. This is not that place, and we loved that. For some maybe that’s not their ideal Key West experience. But this was...