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SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool

Guesthouse in Key West, 10-minute walk to Duval Street

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Photo gallery for SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool

Welcome to The Simonton Room
Plush linen
Cheery surroundings
Cozy bedding
Flat screen TV

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Pool
  • Free WiFi
  • Air conditioning
$382
avg per night

Explore the area

View in a map
Key West, Florida
  • Place, Duval Street
    ‪9 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪14 min walk‬
  • Place, Southernmost Point
    ‪4 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪12 min drive‬

Rooms & beds

1 bedroom (sleeps 2)

Bedroom 1

1 King Bed

1 bathroom

Bathroom 1

Bathtub or shower · Toilet

Spaces

Deck or patio
Balcony
Price is $382 avg per night

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About the neighborhood

Key West

Located near the beach, this guesthouse is in Old Town Key West, a neighborhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and Florida Keys Beaches. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with ecotours and cycling.
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What's nearby

  • Duval Street - 9 min walk - 0.8 km
  • Ernest Hemingway Home and Museum - 14 min walk - 1.2 km
  • Harry S. Truman Little White House - 15 min walk - 1.3 km
  • South Beach - 19 min walk - 1.6 km
  • Southernmost Point - 4 min drive - 2.4 km

Getting around

  • Key West Intl. Airport (EYW) - 9 min drive

Restaurants

  • ‪Kermit's Key West Key Lime Shoppe - ‬11 min walk
  • ‪Cuban Coffee Queen Waterfront - ‬7 min walk
  • ‪Schooner Wharf Bar - ‬10 min walk
  • ‪Half Shell Raw Bar - ‬8 min walk
  • ‪Square Grouper Key West - ‬7 min walk

About this property

SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool

CAPTIVATING CLASSIC REVIVAL CHARM...
Built in 1894, the delightful Inn on Fleming is an 11 room boutique hotel that was once the residence of Board of Education chair Glynn Archer until it was transformed into what is now a serendipitous tropical refuge, boasting 9 unique rooms and suites and tucked into a peaceful residential street. You are only two blocks from the Historic Seaport and a short stroll to 5 star restaurants, bars, shopping and the endless allure of famous Duval Street. Whether you're looking to hook your catch of the day, visit upscale art galleries, or swim with the dolphins, let us be your home away from home in paradise.
***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.
***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas.

DETAILS AND AMENITIES...
The magic begins as you step onto our cozy wraparound porch with comfortable and plentiful seating, where you are immersed in the unique sights and sounds of our charming neighborhood. The spacious kitchen, dining and cozy living areas are located on the main level of the inn. Retreat to our tropical garden to savor a cup of coffee in the morning. Sip on a crafted cocktail in the afternoon and take a dip in our lush tropical heated pool featuring a soothing and relaxing waterfall. Indulge yourself with a favorite novel or explore the internet with free Wi-Fi. All of our rooms include an en-suite bathroom, Serta PerfectSleeper Prestige Suite 11 Mattresses, fine linens, flat screen TV, coffeemaker and a mini-fridge, countertop ice machine, as well as tropical garden views. Our concierge services can advise you about all the things to do, including reservations to snorkel, kayak in the mangrove channels, or relax on an evening sunset sail.

SLEEPING ARRANGEMENTS...
The Simonton Room is located on the 1st floor and offers a plush king bed. Indulge in this lovely modern setting that offers a spacious private bathroom with a shower/tub combination. Unwind and enjoy your flat screen TV and sip on a beverage from your mini-fridge.

OUTDOOR LIVING...
Find your serenity and let your mind melt, listening to the soft rush of our pool waterfall. Enjoy cozy conversation and frosty beverages under the shaded pool tables, surrounded by lush foliage and sultry island breezes. Stroll through our garden that envelops you in lush mature landscaping and soothes your soul with tropical breezes. Bikes are available to rent for your outdoor adventures.

PARKING...
We do not have our own parking but there is plenty of free on-street parking. Please refrain from parking in spots marked "resident permit".

PETS...
This is not a pet-friendly inn.

DISTANCES TO BEACHES...
Simonton Beach...0.8 mi
Fort Zachary Taylor...1.5 mi
South Beach...1.2 mi
Higgs Beach...1.5 mi
Smathers Beach...2 mi

Cancellations requested at least 30 days prior to arrival receive a full refund.
Cancellations requested at least 14 days prior to arrival receive a 50% refund.

BE OUR CHERISHED GUEST...
Our prices include all fees. No hidden fees.

Amenities

Pool
Free WiFi
Air conditioning

House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Adults only
default

Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Safety features at this property include a fire extinguisher, a smoke detector, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

Frequently asked questions

Does SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool?

As of Feb 13, 2026, prices found for a 1-night stay for 2 adults at SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool on Feb 24, 2026 start from $510.53, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool pet-friendly?

No, pets are not allowed at this property.

What time is check-in at SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool?

Check-in begins at 3:00 PM.

What time is check-out at SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool?

Check-out is at 11:00 AM.

Where is SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool located?

Located in Old Town Key West, this guesthouse is within a 10-minute walk of Key West Burlesque Theater and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 1 mi (2 km).

SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool Reviews

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 22 out of 27 reviews
Rating 8 - Good. 4 out of 27 reviews
Rating 6 - Okay. 1 out of 27 reviews
Rating 4 - Poor. 0 out of 27 reviews
Rating 2 - Terrible. 0 out of 27 reviews

10/10

Cleanliness

6.0/10

Amenities

8.0/10

Property conditions & facilities

10/10

Check-in

9.8/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Pat M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful location - walked everywhere. The house was well appointed and the room was super comfortable! Really enjoyed our stay!
Stayed 5 nights in Nov 2025

8/10 Good

Christine T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
All contact was virtual. Beautiful old home with spacious kitchen access
Stayed 3 nights in Jan 2026

10/10 Excellent

Andrea R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Super quiet with the exception of one night. Really nice linens and comfy bed! I really liked that this stay had a filtered water machine for guests to use AND the insulated pitchers were wonderful to use. There was great shower water pressure and plenty of hot water. I would stay here again.
The Inn on Fleming
Fort Zachary beach
Date & Thyme
The Grand
Stayed 4 nights in Nov 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

A guest from Naples, FL

Excellent

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Close to Duval Street. Very clean. Beautiful property

10/10 Excellent

Donna H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Home away from home

The Inn was very well kept, very quiet, comfortable, and clean. We enjoyed our stay very much and it was in a great location.
Stayed 2 nights in May 2025

10/10 Excellent

daniel s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise

We had the best time while Visiting key west
Stayed 2 nights in May 2025

10/10 Excellent

Maggie B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Rey nice clean property! We were not there to watch TV but very difficult to navigate! Absolutely would recommend to friends!
Stayed 2 nights in Sep 2025

10/10 Excellent

John K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great room in a nicely renovated old house. Looks just like the pictures. Liz and Dwell team were easy to communicate with and responsive to any needs and recommendations. Would stay here again. Close walk to anything on the island. (Uber's from airport). Awesome front porch and nice pool.
Stayed 5 nights in Aug 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Great Stay!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: Came in for a quick trip to key west, looking for rest, relaxation and a little fun. Dwell and the Inn on Fleming hit the spot! :)

10/10 Excellent

Leticia L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was wonderful. Everything I asked for was at my fingertips. Everything was walking distance
Stayed 6 nights in Jul 2025

10/10 Excellent

Robert E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Spot Perfect Location

Amazing house in a beautiful area. Wonderful front porch for hanging out. Walk to everything.
Stayed 2 nights in Apr 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Pamela H.

Key West Vacation- May 2024

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location, quiet area, very clean, owner answered all our questions. Thanks for a great stay!

10/10 Excellent

Kathy D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great, quaint gem in the heart of Key West

Perfect place to stay. Love the charm of the old house/ mansion and the updated modern conviences. Within walking distance of Duval Street and other attractions. The extras of breakfast food, soda, wine, beer, were a pleasant aurora.
Stayed 2 nights in Mar 2025

10/10 Excellent

Sue G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved everything about our room, and the Inn on Fleming, it’s a great location in a safe, quiet, historic neighborhood. Walkable to Duval and to the waterfront. The Simonton room is large, high ceiling, with fan and air conditioning. There is a fridge, tabletop icemaker, and Keurig. Coffee pods, cream and sugar are provided. Bed was comfortable, plenty of towels, and super clean bathroom. We had access to the home, porch, deck, pool. There are dishes, cutlery, wine glasses to use as well as kitchen space to prep and serve food. Lovely sitting area, place to leave luggage if you arrive early. A concierge is available, as well as a virtual innkeeper - easily reached by text, and prompt replies. We loved everything about our stay, and would definitely choose to stay there again. Oh, and the holiday decor was gorgeous and festive!
Front entrance and foyer
Sitting area
Christmas tree
Kitchen area
Stayed 5 nights in Dec 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Hope A.

Love Love love

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Everything about this little Inn was special and unique. We always felt safe, even though the front door to the Inn stayed unlocked for all guests. Everyone in Key West is so welcoming.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Barb S.

A hidden gem

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The inn was amazing! We had a king bed room with private bathroom. Kurig, ice maker, fridge and freezer, and dehumidifier in room. Extremely clean and comfortable. Common area was amazing! Well equipped kitchen, kurig, ice maker, microwave, stovetop, dining area, and sitting areas. Front porch, lounge chairs and small pool in the back. Bike rental onsite. Virtual check in and out. By far the best stay yet. Only negative was the tv kept buffering. After a long day we just wanted to veg and watch tv and we’re not able to.
This review comes from a trusted partner site and has not been verified.

6/10 Okay

Janet E.

Not Great

Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was very happy with the location. I was somewhat dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: We discovered this property last year and had such a great experience we booked again this year. The Inn was clean in the common areas and when we arrived. However, trash was not collected at any time during our stay, towels were not refreshed, dehumidifier stopped minutes after we arrived and was not remedied. Our previous stay, a selection of muffins and fruit in the AM, a choice of wine in the evening and the service of our rooms made the stay special. None of those amenities were offered this year. 2 other guest were told they could prepare a meal, only to find microwave the only source to prepare their food. Location is awesome, just a bit spare on service and amenities. Easy walk to anything you might want to see and do.

10/10 Excellent

Dominque I.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect key west stay!

Absolutely love this adorable property and will be back! The room with connecting bathroom was perfect. The check in was super easy, we obtained a key to the room, which was nice because we were right at the front of the house! There was a mini fridge with freezer, ice maker and coffee machine the in the room which was very convenient. The entire home was adorable, I loved it! We didn’t use the pool but it was the perfect size for a couple to relax, the location was great, just a 5 minute golf cart ride to pretty much anywhere on the island!
Stayed 4 nights in Jun 2025

10/10 Excellent

Uyanga G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to stay in Key West

The place looks even better in person. Pictures don’t do it justice! Super clean and cozy. The entire place is maintained very well. The only tiny issue we had while staying there was the slow internet.Enjoy our stay & highly recommended!
Stayed 2 nights in Dec 2024

8/10 Good

Melissa

Liked: Cleanliness, amenities, property conditions & facilities, communication
You always hope you get what you paid for and we did. We were lucky enough to find parking close and could walk everywhere. I love old homes they, have lots of character and this one is beautiful. The access to a kitchen was perfect too since we make our own brunch. The staff was super friendly. I really enjoyed our stay there. It was a nice treat.
Stayed 2 nights in Feb 2025

10/10 Excellent

Anne L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend getaway

Everything was clean. .amazing ...nice to have coffee and creamer in room....loved the water pitchers. Oranges in kitchen were a nice touch. I think the only thing i would change is locking the front door at night.
Stayed 2 nights in Mar 2025

8/10 Good

Michelle

Liked: Cleanliness, property conditions & facilities, communication
Disliked: Amenities
Recommend a key pad for the front door. We were on the first floor next to the front door with no lock.
Stayed 2 nights in Mar 2025
This review comes from a trusted partner site and has not been verified.

8/10 Good

Michelle M.

Beautiful and cozy

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was somewhat unhappy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: One of the smallest rooms, next to the front door which is left unlocked. Recommend implementing a front door keypad for visitors staying at the property.If I stayed there alone, I would not have felt safe.

10/10 Excellent

Carolyn P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfection

We were made to feel welcomed. Met some great people. Wendy the owner stopped by and we chatted and Liz was so helpful. I wanted to stay longer. Our room was a haven from the heat and everything was crisp and clean. It felt like you were staying with family. Walking distance to Duval Street. We were permitted to use the amenities before and after check out while we waited for our boat back to Fort Meyers. Met Bill a retired lawyer and a lovely family from up north that we chatted in the pool. Fresh oranges left out in a bowl and coffee pods stocked I’d love to go back again. We took the Ferry from Fort Meyers to Key West and it was a three block walk to the Inn. Flemming street is beautiful and mature Ubers are fast and cheap if you want to avoid the heat and walk back to the inn
Our room 1st floor. Quiet and cozy
Bathroom clean and tub
Chairs by the pool jacuzzi
Front door
Stayed 1 night in Jul 2025

10/10 Excellent

Richard K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Jul 2025