Name: Simonton Court Historic Inn & Guesthouse
Address: 320 Simonton St, Key West, 33040, US

10/10

Exceptional

12 Jul 2026

Jeff

My husband and I had a great long weekend at the Simonton Inn. They were very responsive to any needs and helpful in every way. We will definitely be coming back at some point!

Family

8/10

Excellent

06 Jul 2026

Molly

Very friendly staff. Convenient location to all the sites without the noise. Note that some rooms are on the top floor of the mansion and as far as we could tell there is no elevator. Breakfast is varied but there are no hot items.

Partner

10/10

Exceptional

06 Jul 2026

Steven

Without question a classic, convenient and beautiful Key West inn. The rooms were spacious, modern and tastefully decorated. Many small pools throughout the property with lush grounds. Nice breakfast served by such caring staff.
Since my stay was in the summer, rates were unbelievably low which was the reason I booked Key West. If the price were right other times of the year I’d be back without question.

Self

10/10

Exceptional

05 Jul 2026

Douglas

Charming
Like being in a tropical garden
Only problem
Was limited parking

10/10

Exceptional

02 Jul 2026

Joan

Such an amazing stay! Was the best place we have ever stayed! wonderful property and amenities! Staff is very attentive to anything you might happen to need and breakfast was delicious 😋 We will definitely be booking here again 😀

Partner

10/10

Exceptional

02 Jul 2026

Nikki

The cutest nicest place we stayed down here. I never would’ve expected all it had walking by. Our stay was wonderful. Would definitely stay again

Family

10/10

Exceptional

02 Jul 2026

Bobbi D

Beautiful secluded property in the heart of old town. Attentive staff. Would definitely book this property again.

Family

10/10

Exceptional

02 Jul 2026

Magali

The only negative point was the breakfast

Family

10/10

Exceptional

01 Jul 2026

Gordon

i would stay there again famlly run hotel

10/10

Exceptional

30 Jun 2026

Bruce

We loved the atmosphere, the multiple pools, the room and the proximity to Duval and Mallory Square. Would stay again in a heartbeat.

Friends

10/10

Exceptional

26 Jun 2026

Laura

I really noticed all the little touches around the facility like the men’s bathroom had a mustache and the women’s had red lips! The flower petals on the walkway, the beautiful postcard, the towels wrapped nicely and in a wicker basket near the pool, the pool chair covers!! Not to mention the wonderful breakfast every morning! Violet was the absolute BEST! So special and welcoming. Had a fabulous stay and will be back again. Thank you so much!!!

10/10

Exceptional

25 Jun 2026

Jill

The service and attention to detail were top tier. The room and public areas were clean and well-maintained.

Jonathan and Violet went above and beyond to ensure my stay was amazing!

10/10

Exceptional

24 Jun 2026

angelica

Super clean, well kept despite being and old property. very very nice and helpful staff made checking in very easy and my stay very pleasant. will definitely be coming back i had a wonderful experience enjoying my time at all 4 pools!

Partner

10/10

Exceptional

21 Jun 2026

Michael

I rarely review places but when I do they deserve it! Simonton Court was top notch. We got a good price for the stay. We arrived to find an inviting flower covered, palm lined inviting walkway. They upgraded us to a king size bed, but that was 3rd floor so we chose to stay in our queen on the first floor. The little houses would have been perfect to stay in. Pools were nice, place clean, breakfast nice, hoped for omelets. Located 1 block from Duval St in the center of everything but far enough for it to be quiet. But all in all I rate our Stay a 9 out of 10,

Partner

10/10

Exceptional

20 Jun 2026

Mari

Beautiful property, wonderful staff. We hope to visit again soon.

Partner

10/10

Exceptional

20 Jun 2026

Jane

Our stay was GREAT. The room really nice and clean. The staff was very kind and helpful. The grounds were tropical and we enjoyed 4 different pools. The breakfast was included and delicious. This hotel is in a great location, a block from the action but quiet. We walked everywhere no need for a car. The parking fee is high per night so we parked on the road without difficulty. We believe this hotel to be the best one we booked since we started visiting the Keys. Will be back.

Partner

10/10

Exceptional

19 Jun 2026

Annemarie

The property is a quiet jewel in Key West, we had a last minute booking and the staff upgraded us! Awesome cottage suite with virtually private pool in a tropical oasis. Yet steps away from all the action on Duval. Breakfast was great, and the pools were so relaxing! No noisy roosters getting you up at crack of dawn courtesy of two cats on property. Only down side was our shower struggled to heat up, but a small price to pay for such a beautiful historic place!

Partner

8/10

Excellent

15 Jun 2026

Rita

Perfcet location and walk to everything , we very much enjoyed our stay!

Partner

10/10

Exceptional

12 Jun 2026

Francis

Very convenient location to the Old Town area. Easy walk to every place

10/10

Exceptional

10 Jun 2026

Kerline

The room was very spacious and clean. The staff were extremely friendly and helpful. I love the way you choose your breakfast and they bring it to you at our table. The water pressure in the shower was awesome. Without a doubt I will return.

Partner

10/10

Exceptional

10 Jun 2026

Kitti

We had an absolutely wonderful stay at this cottage in Key West! The property was spotless from the moment we arrived, and it was clear that cleanliness is a top priority. The cottage was beautifully maintained, comfortable, and had everything we needed for a relaxing getaway.

The staff was exceptional—friendly, welcoming, and always available to help with any questions or requests. Their attention to detail and genuine hospitality made us feel right at home.

The amenities were great, we got to make our own wind chimes while enjoying some cocktails. Everything was thoughtfully provided, making our stay convenient and enjoyable. The combination of a charming cottage, excellent service, and great amenities made for a perfect Key West experience.

We would highly recommend this property to anyone visiting Key West and can’t wait to come back!

Partner

10/10

Exceptional

09 Jun 2026

Shawna

Location was excellent. We walked everywhere and never felt like things were too far. Every staff person was so kind and helpful. We had some issues and we were immediately upgraded and the rooms were beautiful! 4 pools on the property, beach size towels were always available poolside. Very good options for free breakfast, good coffee. 24 h access to cold filtered water. Lush tropical garden layout. Surprisingly quiet given the proximity to Duval St. slept great, good linens. Really was a beautiful oasis. To Jonathan, Violet and Kemola, you made us feel special and welcome. Thank you so much!

Partner

10/10

Exceptional

08 Jun 2026

Daniel

When you come into the gated area, all noise disappears and you feel like you are in a tropical forest. The staff is fantastic. The main pool is a great place to socialize. The room was very comfortable.
If I do have one complaint [and this is not a complaint] the bathroom in our room was very small.

Partner

10/10

Exceptional

07 Jun 2026

Evan

Simonton was amazing! It felt like you were in another world while on property. Mature foliage, cute cottages, and amazingly helpful and courteous staff. The rooms were on the older side but everything was well maintained and very comfortable. It was close to EVERYTHING as well we parked our car in their lot and didn’t use it once the entire time since everything was within walking distance. 10/10 recommend.

Partner

10/10

Exceptional

05 Jun 2026

Elaine

This place is a gem! This place is beautiful! They treat you as their personal guest, even a hand written welcome card. The staff, rooms, service from employees there was the best and better than any hotel. Kudos to Violet and the the front desk Gentleman and Karmala. Thank you for a wonderful stay.

8/10

Excellent

05 Jun 2026

Jeri

The room was clean and comfortable. The bathroom was to warm. No A/C piped into it. The townhouse we stayed in has many skylights over the bed which allowed way too much light in the bedroom for sleeping. All of the porch lights and lighting around the complex with no ability to close curtains, was a problem for us. We were not aware of the lack of parking and received a last-minute notice from the B&B about where we planned on parking. Make sure when you make the reservation, you get the parking. The staff was fantastic and the location of the property is ideal. I would return now that I know what to ask for regarding parking and which unit has blinds. Recommend asking for a ground flood unit.

Partner

8/10

Excellent

04 Jun 2026

Michelle

This place was warm and welcoming. Everyone we came into contact with was fabulously nice and pleasant. The breakfast was good. Air conditioning worked. The bed however was a little lumpy and difficult for decent sleep.

Partner

10/10

Exceptional

02 Jun 2026

Steve

Cottages in Lush Green surroundings in Old Town area! You can walk to everything Key West has to offer!!

Partner

10/10

Exceptional

31 May 2026

Magdalena

my stay was excellent the staff was the best. I will sure return to this hotel

Self

10/10

Exceptional

31 May 2026

Timothy

I can't believe how much we enjoyed staying here! So nice! The property is beautiful. The staff was excellent. The room was very quiet and comfortable. The location is perfect! One block from Duval Street. 5 minute walk to Mallory Square. We can't wait to go back!

Partner

10/10

Exceptional

28 May 2026

Doug

Beautiful property with a number of different pools. The breakfast was excellent along with all of the staff.

Family

10/10

Exceptional

23 May 2026

Samantha

Room was big, clean, and had amazing AC. Many pools and complimentary breakfast. The location was super convenient as well. We loved it and would love to stay again

Partner

10/10

Exceptional

23 May 2026

Hiram

Clean room

Partner

10/10

Exceptional

22 May 2026

Olha

Great stay overall! Friendly staff, clean rooms, and a perfect location for exploring the Keys and relaxing in this little paradise 🌴

Partner

10/10

Exceptional

20 May 2026

Adam

This property is our favorite in Key West. I gives you that old time Key West feel. The grounds are gorgeous and well kept. This property offers easy access to everything(beach, food, sights, and bars). The staff are amazing. They are very helpful and friendly. This is the best stay on the island.

Partner

10/10

Exceptional

19 May 2026

Greg

The staff really stood out at this place! Very impressive!! Rooms were very clean.

Partner

10/10

Exceptional

19 May 2026

Ian

Breakfast was delicious.

10/10

Exceptional

18 May 2026

Joe

Excellent place to stay! Convenient for walking to anywhere close to Duvall Street.

Friends

8/10

Excellent

12 May 2026

Christoph

Easy breakfast, great for on the go. Beautiful pools. Room A/C was great.

Friends

10/10

Exceptional

09 May 2026

kelly

Defiantly would stay again and so close to everything

Friends

10/10

Exceptional

08 May 2026

Patrick

The staff is super friendly. The room was smaller than I was expecting, but very clean and unique. I had some problems with the mattress in the room, but the manager did his best to fix it. Excellent location. Within walking distance of pretty much everything. We are planning to stay here again next year.

10/10

Exceptional

07 May 2026

Meghan

The staff is always the best. Jonathan is amazing and always so attentive and appreciative. He remembers us every time we come there and makes sure we are taken care of. He needs a raise!

Family

8/10

Excellent

01 May 2026

Amy Lynn

Front desk staff were amazing. Very friendly and helpful. Loved the little tour of the grounds that we got when we checked in. We stayed in room SC1. The only notable issues that I had with our stay were:
1.) The bed was TERRIBLE. Seriously terrible. It was so worn that there was 2 visible dips in it. We did talk to another couple who had the same comments about the bed in their room.
2.) Room darkening drapes would be helpful on the windows in this room. The courthouse is directly across the street and they have several very bright LED lights on the front of the building that are on all night. We ended up closing the shutters along with the drapes and that helped a little.
3.) The bathroom has a window that looks out onto the balcony of the room next door. There is a mini blind on this window, but it stands away from the window about 2”. If someone would happen to be on that balcony and look towards the room, they would be able to see you sitting on the toilet. I would suggest that some frosted Contact paper be put on the bottom pane of this window to avoid that.

As I previously stated, every staff member was wonderful. Eric, who is the happy hour host, was an absolute delight. His seashell windchime class was awesome. The option of 4 pools was amazing and the entire hotel grounds is absolutely beautiful.

Partner

10/10

Exceptional

28 Apr 2026

Mike

The courtyard was beautiful and relaxing especially at night. Staff was very accommodating and helpful. Bed was comfortable. Being able to have breakfast on site was a nice way to start the morning at a slower pace. It was a bit noisy but that is to be expected based on the location.

Partner

10/10

Exceptional

26 Apr 2026

Melanie

Really interesting old property in the heart of Key West. Every room is different; evidently these cabins were housing for the workers of a cigar factory back in the day. Lovely garden pathways between the rooms, four different little swimming pools scattered around the cabins with one large \"main\" pool at the main courtyard/breakfast area. It felt private and intimate with foliage hedges between each of the guest quarters. We had a 2nd floor room with a little living room, tiny deck and pool out front which was really neat. Super helpful and congenial staff. It's not the most affordable place I've ever stayed, but one of the most memorable. Great location, walkable to everything in the Duval area of Key West. I'd definitely go again!

Partner

10/10

Exceptional

24 Apr 2026

Rebekah

Beautiful property and extremely comfortable bed.

Partner

6/10

Pleasant

22 Apr 2026

Richard

Yes.

Self

8/10

Excellent

20 Apr 2026

Ric

The staff was the best part of the experience. Jonathan and Violet were outstanding with their welcoming attitude and were very helpful whenever we needed something. Other members of the front desk staff and housekeeping were also very helpful and friendly.

Friends_and_family Family

10/10

Exceptional

18 Apr 2026

David

Our 2nd time in key west. Last b&b was great. But simonton was fantastic. The property is perfect. Quaint vibe. Lots of trees and local wildlife. A perfect place to relax and soak it all in. This place is located in a perfect place to reach everything key west offers within a 10 minute walk. The people who work here were amazing. Some of the nicest. We arrived early and they held our bags. Texted us when they were ready and already put our luggage in the room. Our return flight left late so we asked if we could leave our bags at the desk while we did some last minute roaming around. They were absolutely accommodating. They said leave them and feel free to stay and enjoy the pool with private restrooms even after we checked out. If this is your 1st time here or coming back again I would highly recommend. Were coming back next year and will absolutely be staying here.

Partner

10/10

Exceptional

16 Apr 2026

Don

Excellent environment, nice property very comfortable. I will return on my next visit.

8/10

Excellent

14 Apr 2026

Jason

Very unique, great staff, and great location

Friends

10/10

Exceptional

12 Apr 2026

Kimberly

Great experience! Multiple pools and very charming setting. Great spot to relax yet close to Duval

Partner

10/10

Exceptional

10 Apr 2026

Peter

Loved our stay here. The staff is so friendly and helpful. The property so quaint and well taken care of. Would recommend to anyone. We will be back for sure!!

Partner

8/10

Excellent

09 Apr 2026

Tina

Clean room. Very comfortable bed! Quaint atmosphere. Friendly staff. Outstanding location for walking to Duvall Street and historic sites.

Family

10/10

Exceptional

05 Apr 2026

Wendy L

The Historic Inn was charming. Stayed on the 4th floor of the Mansion. A hike up but really was no problem. Loved the excellent morning breakfast and sitting by the pool seeking or evading the sun! Used 2 bikes to go watch a sunrise. Surreal! Could walk all around Duvall Street without feeling unsafe. Only negative was the music in a bar establishment on the other side of the property’s pool wall was obtrusive if you didn’t like the live talent. Started mid afternoon and went to 11:00.

Partner

10/10

Exceptional

03 Apr 2026

Kate

The service was out of this world. We would head down for breakfast at the hotel and the room would be refreshed immediately upon return. The staff was always friendly and making sure our needs were met. I don’t think there’s a disappointing room on the grounds but we especially enjoyed the direct access to the street side porch with rocking chairs. We will definitely be back.

Partner

10/10

Exceptional

25 Mar 2026

Heidi

Fabulous stay! Quaint cottages in garden setting right in old town. Very convenient to Duval St. Wonderful staff, nice breakfast. Rental bicycles available on site for $20 a day. Clean room, mattress was a little hard for my preference but that was the only tiny negative. Would go back!

Partner

8/10

Excellent

24 Mar 2026

Jaye

Lovely property and a great location. One block away from Duval St. This is an older property, so you will hear noise from other guests in adjacent/above units. Older AC units and a dehumidifier would be most helpful. Erick was just the nicest fellow - had fun making wind chimes.

Partner

8/10

Excellent

16 Mar 2026

David

Excellent location and atmosphere. Room itself needed more space in the bathroom for toiletries. Luggage racks would have been helpful also. Staff was very friendly and helpful.

Partner

10/10

Exceptional

13 Mar 2026

Becky

Great location. Cool vibe.

10/10

Exceptional

01 Mar 2026

Thomas

Room was very clean,well furnished and staff were all very friendly. This was our 6th time staying here and it never disappoints.

Partner

6/10

Pleasant

28 Feb 2026

Marlene

The room was good, the staff was very nice and accommodating for us.
We should have been in our room at check-in time by 3pm. We arrived around 1pm, told us it was not ready

10/10

Exceptional

27 Feb 2026

Nathan R

Our favorite place in Key West.

Partner

10/10

Exceptional

19 Feb 2026

RICHARD

Excellent staff!

10/10

Exceptional

03 Feb 2026

Ann

Such a cute place! Staff was very courteous and attentive. Location is perfect for walking around Old Town. Room was very clean and bed was comfortable.

Leisure Partner

10/10

Exceptional

30 Jan 2026

Jennifer

Great stay, clean room, and amazing staff!

Leisure Partner

10/10

Exceptional

19 Jan 2026

Jonathan Van

Wonderful and welcoming staff. The grounds are beautiful. Proximity to Duval Street was perfect. We will definitely stay here again.

Leisure Partner

10/10

Exceptional

17 Jan 2026

anita

Charming getaway in old town. Nice vibes and super quiet. Rooms and property beautifully architected and decorated

Leisure

10/10

Exceptional

11 Jan 2026

Casey

Very friendly, accommodating staff.
Convenient location right off Duvall St.
Clean, comfortable, well-maintained rooms.
Beautiful courtyards and pools. Amazing landscaping and outdoor lighting.
Breakfast is waffles, toast, eggs, fruit, yogurt, etc in the courtyard. Very good waffles!
We will return for another stay.

Partner

10/10

Exceptional

10 Jan 2026

Chris

Loved this place and would stay here again! The room was spacious and clean. But it is the historic charm of the buildings and the grounds that makes it special and unique. Great location as well.

10/10

Exceptional

06 Jan 2026

Tina

Excellent in every way!

10/10

Exceptional

05 Jan 2026

William

Great location just close enough to all the action. Management and staff are really good. Clean and well kept. We would gladly stay there again.

Leisure Partner

10/10

Exceptional

05 Jan 2026

Jesus

Great location and staff. The room was clean and comfortable, nice and quiet.

Leisure Partner

10/10

Exceptional

03 Jan 2026

Debra

We picked a deluxe queen, the room was extremely comfortable. Staff was always courteous & efficient, and answered our many questions during our week stay. This beautifully landscaped facility is two inn units with additional cottage units disbursed throughout the property.

Leisure Partner

10/10

Exceptional

03 Jan 2026

David

We were on a road trip so our decision was last minute, but our experience was EXCELLENT. We stayed in one of the cottages. It was the most comfortable, clean and private accommodations we’ve ever had. The staff was great and the property was amazing. It felt like we were in your own private garden. Thank you.

Leisure Family

8/10

Excellent

30 Dec 2025

Kate

Beautiful, charming hotel in a great location. A wonderful option in old town key west.
Only complaint was about the TV - it was very small and outdated. It’s something many guests wouldn’t care about but it’d be an easy, inexpensive upgrade for the hotel to make.

Partner

10/10

Exceptional

27 Dec 2025

Somy

Price

10/10

Exceptional

27 Dec 2025

Kaye

The old charm of the place was just what we were looking for. The staff were so friendly and helpful. We would definitely come back!

Leisure Family

10/10

Exceptional

24 Dec 2025

Tiffany

I loved staying here! The room was great and the staff was awesome!

Leisure Friends

10/10

Exceptional

21 Dec 2025

Shelley

Perfection!!!

Leisure Friends

8/10

Excellent

19 Dec 2025

Beverly

The manager and his wife were so personable and always gave great suggestions when asked. We will definitely be returning.

Leisure Partner

4/10

Poor

19 Dec 2025

Kathryn

Several years ago, we discovered Simonton Court unexpectedly. That stay was charming and memorable, and I recommended the hotel to others. Based on that experience, we booked again recently through Expedia and the difference was shocking. From the moment we arrived, things went downhill. We arrived early and called to ask to be notified when our room was ready, which they did later that afternoon. At check-in, we were told there was no onsite parking and that we’d need to park several blocks away in a paid lot, after we had already paid significant money to park all day. I was then told parking had been available earlier and that I “should have told them” I needed parking when I first called. There was no way for me to know this. Next, we were informed we would need to change rooms during our short three-night stay because we booked through Expedia. This was framed as an Expedia issue, though it made no sense. The situation was only resolved after extreme frustration, multiple complaints, and frankly, tears, something no guest should experience on vacation. The staff member at check-in was shockingly unprofessional, dismissive, and seemed to enjoy escalating the situation rather than resolving it. I work in a customer-facing profession and would never treat someone this way. Our room this time was on Simonton Street, loud, with no view. The bathroom was extremely small. The pool was dirty, no pool towels, and the bar was almost never open. Be warned. Stay elsewhere!!

Leisure Partner

10/10

Exceptional

16 Dec 2025

Darbie

Amazing property and top notch service. Will definitely return.

Leisure Partner

8/10

Excellent

15 Dec 2025

Tamara

Our room had a moderate odour of urine at moat times which is unacceptable for a room we paid $750/night for. Housekeeper only made our bed but didnt take garbage or replace glasses that were used but did bring towels when we requested.
The property is beautiful and pools lovely and location excellent.

Leisure Partner

10/10

Exceptional

12 Dec 2025

karen

Great place to stay in Key West. Lovely setting, close to the action, and the staff was amazing. Would recommend Simonton Court as the place to stay and relax in Key West.

Leisure Partner

10/10

Exceptional

11 Dec 2025

Jennifer

Stay here! We’ve walked past Simonton Court dozens of times on previous trips to Key West but never realized how beautiful this property is, until we stayed here. The property is expansive, stunning, lush and quiet with 4 pools. Although it’s sold out, it feels as though you have the place to yourself. The rooms are all different and cozy! We’ve stayed at the large luxury resorts here and would never ever do that again- the experience is like night and day. What makes this even more special is the staff- they go above and beyond (starting with a personal tour of the property and offering to make your stay stellar in any way). Jonathan and Violet are wonderful!!! We found our new favorite place in Key West! We loved it so much we extended our stay.

Leisure Partner

10/10

Exceptional

01 Dec 2025

doug

The staff was really nice

Leisure Family

10/10

Exceptional

29 Nov 2025

Sharon

This is a lovely place to stay when in Key West! Very safe area, close and walkable to Duval St, many nearby restaurants … the staff are warm and welcoming! Beds are comfy- highly recommend!!!

Leisure Partner

10/10

Exceptional

19 Nov 2025

Gene

Room was super clean, as always.
Staff is always amazing.
Very cool place. Old Key West style.
Great location, close to everything Old Town.
I only stay here everytime I come to Key West

Leisure Friends

10/10

Exceptional

16 Nov 2025

Otto

Just a great place. Location is fantastic and the property is beautifully cool. This is our first time here but it won’t be our last. The staff were all polite, professional and very accommodating.

Leisure Partner

10/10

Exceptional

12 Nov 2025

Morgan

Super friendly staff, cute bed & breakfast feel. Access to all 4 pools. Highly recommend staying here. Can’t wait to go back.

10/10

Exceptional

12 Nov 2025

Tara

Beautiful, hidden oasis in the heart of Key West. Exceptional staff who go above and beyond to ensure you have a relaxing and memorable stay. I can not wait to return.
Everything was fantastic.

Self

10/10

Exceptional

03 Nov 2025

Leonid

Really enjoyed my stay. The staff were super friendly, and the location was amazing—close to all the Old Town activities!

Leisure Family

10/10

Exceptional

02 Nov 2025

Lynn

Quiet place and room was big with a double shower plus an outside deck ! Friendly staff and you cannot beat the location. One of our favorite places. Breakfast is limited but just enough to get you going.

Friends_and_family Friends

10/10

Exceptional

29 Oct 2025

Kevin

Perfect place

10/10

Exceptional

28 Oct 2025

Damian

Very good

Family