What a fabulous stay in the heart of Key West! My husband and I stayed here for our honeymoon, and arrived exhausted after a red eye flight and a completely sleepless night. Staff were super welcoming and able to check us into our room well before the technical check in time, which was amazing considering all we wanted to do was lay in a bed! The grounds are absolutely beautiful, lush with greenery, and multiple cottages, allowing a very private feel that was so different from any hotel property I’ve ever stayed at. They have resident cats on the property too! Alvin was my dude, always chilling at your feet. They have multiple pools available for all guests to use as well. We were lucky enough to get one of the cottages and absolutely loved it! It had all the comforts and coziness of being in your own home, with touches of vintage charms in an upgraded modern vibe. There’s a complementary breakfast with a small bar available on property. It’s centrally located to Duval street, so we were able to walk everywhere! Don’t even rent a car. Get an Uber into the city and enjoy your time walking or biking around. If I ever find myself back in Key West, we’ll definitely be staying here again!

I was very impressed with the service and friendliness of the staff. I stayed on the third floor of the mansion and it was beautiful. The entire location is amazing and I love the activities from yoga to painting postcards and coconuts. The complimentary breakfast is also very fresh and something I look forward to every morning.

Nothing could have been better for our stay for our wedding weekend. We used one of our cottages as our room for the week, our bridal suit, and the girls getting ready room. The staff was so accommodating to our several requests, the beds were so comfortable, and our pictures for our first look were incredible. It provided such a relaxing setting walking into the gardens, and in Key West, large rooms are hard to come by. We had sooo much space! 10/10

We stayed here for part of our honeymoon and it was an absolute dream. The staff was very friendly and allowed us to leave our luggage at concierge until our room was ready since we got in town early. They gave us an upgrade to one of the cottages which was a lovely surprise. The rooms show their age but it adds to the Key West experience and did not bother us. The filtered water dispenser by the pool area was a huge plus for us. We loved how peaceful, well kept, and homey this hotel was. The location cannot be beat as it's close to everything yet still quiet at night and we felt very safe since they lock the main gate. Perhaps our favorite part of the Simonton was our buddy Alvin, who is their pet cat that was a welcomed visitor on our porch everyday. We cannot wait to come back!

Fantastic stay from check in all the way through to check out. Our cottage was incredibly charming and the grounds were beautiful. The entire staff raised the bar on what hospitality should be. Just a block off Duval St, close enough for an easy walk, but far enough away to be a nice refuge at the end of the day. Can’t wait to return.

Great place overall. Staff was very accommodating and helpful with suggestions of things to do or where to eat. They have 4 pools that are open 24 hours and the breakfast is a good way to get the day started. Rooms were nice and bed was comfortable.

We stayed at Simonton Court for two nights, three days. We were in one of the cottages. The accommodations were perfect for sharing with a friend. Clean and conveniently located to Duval Street. Loved meeting Janeen and had so much fun painting postcards with Erik! Every employee we encountered was so nice, great customer service! We will definitely be back!!!

This place is just fantastic, no other word for it. Rooms were great, nice pools. Great location. We were there for 4 nights, but originally I was only booked for parking for 3. So was a bit worried about getting parking for the one night, not from around the area visiting from UK and seemed to be loads of areas where could end up getting towed. But they sorted it which I was very grateful for. It's like a little community not a hotel. Cottages are fantastic we stayed in CO4 which had a porch, split level rooms. And was just so great to use as a base. Close walking to everywhere as well. Many thanks for making our stay in key west so good. Steve Harrison

I had only two nights in Key West for my birthday and selected Simonton Cottages to have easy access to things and to be able to have parking. From the first contact and throughout, they communicated well. Then, when I checked in, the pleasant surprises began. They guided me to my reserved parking spot and showed me the grounds, which are a hidden foliaged haven, with four different small pools with sitting areas to be discovered. Stepping into my room, I found a wonderful birthday card and treat! The room was suitable, and had a small private outside area with just enough room for two chairs. I did not realize there was no mini fridge or microwave, but that was fine for my needs, I popped out to Duval Street multiple times as it's literally down the block, so I was able to enjoy the vibe even though I wasn't there to party and was in early. The noise of others partying did not disturb me as some others experienced, so I slept well. As hoped, the location allowed easy access to walk to my boating adventure, the pier, and many other places. As far as the parking cost that others mentioned, it was $25 a day but optional and well worth it to me. You must reserve ahead as the spaces are assigned and limited. I was disappointed in the breakfast options as it was something like $20 for a menu you can check off to get several options (waffles, fruit, etc) but they were not good for me (no bacon or sausage and the only egg option was boiled) so I chose somewhere else. While I would seek less costly options in other circumstances, this was perfect for my needs on this visit. As long as a business is up front about the cost of things (which they are), I can choose whether they are worth it to me or not, and I really appreciate that!

This place is wonderful! We stayed one night recently and could not be more pleased with the ambience and hospitality provided. Every staff member we encountered was extremely friendly and hospitable. At check-in, Rachel gave us a tour of the property and explained the history of this hotel (it was originally a cigar factory). The grounds are beautiful, as was our room. Although our room was directly situated on busy Simonton Street, there was no noise disturbance inside. The room had a sitting area with a television (and cable service) and a separate bedroom with a very comfortable queen size bed. The room was well-appointed and the bath had a generous supply of upgraded toiletries. There are four swimming pools, one with a black surface which helps keep the water almost bath temperature. The grounds are beautifully landscaped with natural Florida foliage and flowers. A most delicious breakfast was served in a quiet corner of the property. Choices included French toast, Belgian waffles, fresh fruit, assorted pastries and breads, as well as coffee and juices. My wife and I highly recommend Simonton Court - we will be back again!

Where to start! This has been one of our favorite vacations and the hotel made it great! This is a gem of a place. The staff are amazing.....very clean and quiet. The charm of the place is overwhelming. We loved their poolside continental breakfast. There were such special touches that made our stay over the top. The cat, Alvi is the most laid back and just hangs around the pool in the shade, not bothering a soul. Roosters and chickens carouse around.......slow ceiling fans on the verandas and billowy curtains blowing in the wind......we can't wait to go back! One more thing, the location is the BEST! One block from Duval Street but quiet so not in the middle of the excitement. If you are going to the Keys, stay here if you are not traveling with kids.....

Absolutely amazing! Impeccable service from staff - they are so nice and were able to give us some great recommendations on food and activities. The hotel is right around the corner from Duvall and the party scene but the grounds of the hotel are extremely relaxing and peaceful. The pools, all four of them, we’re great and clean! Highly recommend!

Simonton Court exudes all of the charm and hospitality one expects to find at a quaint hotel such as this. One, if not- the best stays i've had! Our wonderful experience began from the first conversation I had while booking the room over the phone. I planned a trip with my mom for her birthday- Simonton went ABOVE and exceeded every expectation to make this one of her favorite birthdays ever. From the room they selected for us, the champagne, the beautiful card, the texts asking us about our experience, the complimentary drinks, THANK YOU FOR EVERYTHING. Special thank you to Eric - Simonton Court is so lucky to have you and you made our stay so personal and wonderful. Good staff is everything- and Simonton Court has the best! Thank you for perfecting all the small details, and the big ones. Can't wait to stay again!!! Simonton will be the ONLY place we stay now in the keys.

We didn't stay at hotel, only attended their Friday coconut painting workshop from 4-6p. Supplies and snacks/drinks provided for $10pp. A lot of fun and friendly host. Front desk staff very pleasant.

Amazing and friendly staff. Great breakfast options included with stay, option of 4 pools to lounge at and everything was very clean. Beds were a little firm for my liking but it’s very cozy and inviting. We have stayed here two times and plan to come back and stay in the future. Hurricane alley is one of my favorite places on the island and located right in the resort. On our most recent trip they were doing a food tour through the resort and it was one of the highlights of our trip. We tried some amazing food in places we would not have thought of going. We also had a great time with the other couples that were on the tour with us. Highly recommend doing the food tour if available when you stay!

I'm in love with this place. We went for our honeymoon and we picked a good one! It feels like a little resort with the multiple homes to stay in, the friendliest staff walking around, the four pools to choose from. The walkways are magical gardens with beautiful lighting. The breakfast is so good! We stayed in SC9 and will always want to go back to that room. It's so cute and right off the black bottom pool. We will be going back!!

Amazing location and extremely clean!! Staff is so helpful and very friendly. Held onto our luggage until our flight and also came every single day to clean our cottage (which many places no longer do since Covid). No complaints at all with Simonton Court. Definitely recommend without a single doubt!!

Beautiful hotel, great breakfast (best we had in weeks while travelling the east coast), 4 pools and always easy to find a chair. Only downside: front desk not very knowledgeable or helpful about parking. On-site parking is limited and was not available, so we asked about alternatives they could recommend: "mmmh I guess there is a parking lot a bit up the street", but did not know anything about pricing, modalities etc. And also did not offer any support in checking. Turned out, we would have to pay 30$ per day there, and each day at 9am walk over to physically pay for another day. Also turned out, 3 streets away there is plenty of non-metered, non-permit street parking. Saved us a lot of $$ and inconvenience. Front desk at a hotel should really know such basic things about the area, especially if on-site parking is limited.

Just loved the place. Beautiful guarded, several swimming pools and a great atmosphere at the evening when all the lights are on and they set out lamps. Good breakfast included and centrally located

Have another review on here giving it only four stars. But when it comes down to it, this place is what Key West is about. Beautiful place. One block from Duval but quiet as it is a walled compound. Beautiful rooms. Four pools. The Black pool is our favorite. Friendly staff. We hope Miller is still there. Great breakfast and wonderful vibes. This may be our last visit to the Keys and we want to stay here really badly. We don't care what it costs. It should be a Five Star hotel. Stayed here a bunch of times and will cherish the memories. Definitely would recommend!!

This place is wonderful! When I checked in and got my keys, they gave me a tour of the property. They were very professional and nice the front desk staff is on their a game. The rooms are very cozy. Comfortable make you feel like at home. This place has four different swimming pools which I thought was pretty cool. Some people even have their own personal and a cottage. In the morning they have an amazing little small breakfast just to hold you over for early lunch. Nothing too special but just right. This is definitely a hidden treasure. I can’t wait to come back.

Last time we went I reserved a specific room months in advance. When i got there they had given my room away without ever telling me nor did they offer me the cheaper rate. They tried to sell it as the same type cottage. It was not. I had to ask to adjust the rate. They could never answer me why they gave my room away 🤷‍♀️. Not cool. Location is great tho! Quiet but also, call ahead about parking. They don't inform you of that either. DEFINITELY EAT AT SARABETH DOWN THE STREET ..... AMAZING

I am so impressed that true customer service still exists. Tanisha, Eric, Diana and Danny were wonderful. The crew at the breakfast bar at the main pool were great too. The linens and pillows were top of the line. Location was perfect.

We had a wonderful stay there, it was like having your own little resort right downtown Key West. With Duval only a block away, the stay was still peaceful and relaxing with the multiple pools and wonderful greenery. Only downside was the wifi in our specific room was not very good. Other than that, the complementary breakfast, amazing staff, and friendly service made it an awesome place to stay on our honeymoon!

My wife and I stayed at Simonton Court 5/16-5/20. The grounds are absolutely beautiful and the staff is extremely friendly and accommodating. Sophia the general manager is both friendly and extremely helpful. I would happily stay there again. If a relaxing vacation with great people, located on beautifully manicured grounds then Simonton Court would be an excellent choice. Read less

What a fantastic place to stay! We checked out a few hours ago and ready to go back now! The only negative thing I can say is having to leave. The staff were so friendly and helpful! The grounds are very tropical and quiet. Getting ready to plan another trip! If you ever plan a trip to Key West make sure to stay here!

Great location close to many attractions. Room was small but comfortable. Beautiful grounds-courtyards & 4 separate small pools. Breakfast service was great. Checkin/out was easy & employees were friendly & helpful. Parking is very limited-highly recommend reserving ahead of time. Would stay again.

A magical property, a gateway to paradise with beautiful palms, orchids and four lovely swimming pools to enjoy. The location can’t be beat, quick walking distance to anything you want to do and reasonably priced bicycle rentals for exploring the island. The continental breakfast is a great way to start the day with fresh fruit and pastry offerings, coffee and tea. We LOVED our beautiful cottage getaway. Thank you so much to Eric, Janeen and the rest of the staff, excellence all around! Hard to leave such comfort and beauty but we hope to stay again in the future!