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

Guest house near Duval Street in Key West

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

Terrace/patio
Dining
Interior
Interior
Beach nearby

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Pool
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Key West, FL
  • 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

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About the neighborhood

Key West

Seaside stay .Within a 15-minute walk of this Old Town Key West guesthouse, you'll find Duval Street and Florida Keys Beaches. Key West Burlesque Theater and Studios of Key West are also within half a mile (1 km).
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What's nearby

  • Studios of Key West - 3 min walk - 0.2 miles
  • Duval Street - 9 min walk - 0.5 miles
  • Ernest Hemingway Home and Museum - 14 min walk - 0.8 miles
  • South Beach - 19 min walk - 1.0 mile
  • Southernmost Point - 4 min drive - 1.5 miles

Getting around

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

Restaurants

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

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Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Internet access

Things to do

  • Communal pool
  • Heated pool
  • Tennis

Room amenities

Entertainment

  • Smart TV with cable/satellite channels

Bedroom

  • Bedsheets provided

Bathroom

  • Bathtub or shower
  • Hair dryer
  • Towels provided

Food and drink

  • Coffee/tea maker
  • Ice maker
  • Refrigerator

More

  • Air conditioning
  • Iron/ironing board

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • This property does not allow children.

Events

No events allowed

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.

Property is also known as

2731-256377

Frequently asked questions

How close is SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool to the airport?

This guesthouse is 3.4 mi (9-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

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

As of Apr 5, 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 May 3, 2026 start from $399, 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.

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

Airport shuttle services are not available at this guesthouse.

How close is SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool to the beach?

This guesthouse is a short 15-minute walk from Florida Keys Beaches and 1.5 mi (7-min drive) from South Beach. Don't forget your sunscreen!

Does SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool offer free breakfast?

This guesthouse does not offer free breakfast.

Is there a casino at SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool?

No, there is no casino at this guesthouse.

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.

Is there free parking at SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool?

Free parking is not available at this guesthouse.

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

Yes, there's a heated pool.

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

There are no spa services available at this guesthouse.

How close is SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool to downtown Key West?

This guesthouse is 0.5 mi away from Key West.

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 29 out of 34 reviews
Rating 8 - Good. 4 out of 34 reviews
Rating 6 - Okay. 1 out of 34 reviews
Rating 4 - Poor. 0 out of 34 reviews
Rating 2 - Terrible. 0 out of 34 reviews

10/10

Cleanliness

6.0/10

Amenities

8.8/10

Property conditions & facilities

Reviews

10/10 Excellent

Jason D.

Liked: Cleanliness
Great little place with even better price!
Stayed 3 nights in Mar 2026

10/10 Excellent

Carlton F.

Liked: Cleanliness
Great location, super clean, very nice to have some space outside of the room with a kitchen, fridge, pool, and all the other amenities - unlike the overpriced hotels. Did not get woken up by chickens. Bed was super comfy. Would definitely recommend!
Stayed 1 night in Feb 2026

10/10 Excellent

Beth M.

Liked: Cleanliness
We loved our stay in Key West and the Inn on Fleming was delightful!
Stayed 3 nights in Feb 2026

10/10 Excellent

Sheila R.

Liked: Cleanliness
Great location and very nice place
Stayed 3 nights in Feb 2026

10/10 Excellent

Heather H.

Stayed 3 nights in Jan 2026

10/10 Excellent

Christine R., Baltimore

Liked: Cleanliness
Clean, cozy room . House has a bed n breakfast feel. Kitchen is shared and has lots of space n offers coffe n tea n filtered water. Locations is great quite side street not far from docks n Duvall Street. Great for a few day stay. Host was easy to contact. Great stay!
Stayed 3 nights in Feb 2026

8/10 Good

Christine T.

Liked: Cleanliness
All contact was virtual. Beautiful old home with spacious kitchen access
Stayed 3 nights in Jan 2026

10/10 Excellent

Sue G.

Liked: Cleanliness
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

10/10 Excellent

Pat M.

Liked: Cleanliness
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

10/10 Excellent

Andrea R.

Liked: Cleanliness
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

10/10 Excellent

Maggie B.

Liked: Cleanliness
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
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

10/10 Excellent

Richard K.

Liked: Cleanliness
Stayed 2 nights in Jul 2025

10/10 Excellent

Leticia L.

Liked: Cleanliness
It was wonderful. Everything I asked for was at my fingertips. Everything was walking distance
Stayed 6 nights in Jul 2025

10/10 Excellent

Carolyn P.

Liked: Cleanliness

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

Craig R.

Liked: Cleanliness
Stayed 3 nights in Jun 2025

10/10 Excellent

Dominque I.

Liked: Cleanliness

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

daniel s.

Liked: Cleanliness

Paradise

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

10/10 Excellent

Donna H.

Liked: Cleanliness

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

Robert E.

Liked: Cleanliness

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

10/10 Excellent

Fernando S.

Liked: Cleanliness
Stayed 2 nights in Mar 2025

8/10 Good

Michelle, Horsham

Traveled with partner
Liked: Cleanliness, property conditions & facilities
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

10/10 Excellent

Anne L.

Liked: Cleanliness

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

Melissa

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
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

Kathy D.

Liked: Cleanliness

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