See all properties

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

Guest house near Duval Street in Key West

Choose dates to view prices

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

A covered porch with wicker furniture, a ceiling fan, and a view of the street.
A beach with palm trees and a clear sky.
A modern kitchen with a marble countertop, a wooden cutting board, a fruit bowl, and a pitcher of water.
A hallway with wooden flooring, white railings, and a door leading to a room with a view.
A modern kitchen with a central island, dark cabinetry, and a large window overlooking a garden.

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
    ‪11 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪17 min walk‬
  • Place, Southernmost Point
    ‪4 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪10 min drive‬

Room options

You may also like

Ad
A hotel with a large pool, multiple balconies, and palm trees.

Blue Flamingo Resort Key West

New Town
  • Pool
  • Hot tub
  • Pet friendly
  • Free WiFi
8.6 out of 10, Excellent, 2,643 reviews
The price is CA $161
CA $259 total
includes taxes & fees
Sep 8 - Sep 9
Blue Flamingo Resort Key West

About the area

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 Theater and Studios of Key West are also within half a mile (1 km).
View more Guest houses in Key WestOpens in a new window

What's nearby

  • Key West Naval Station - 4 min walk - 0.4 km
  • Duval Street - 11 min walk - 0.9 km
  • Ernest Hemingway Home and Museum - 17 min walk - 1.5 km
  • South Beach - 19 min walk - 1.6 km
  • Southernmost Point - 4 min drive - 1.4 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
  • ‪Pepe's Cafe - ‬7 min walk
  • ‪Harpoon Harry's Restaurant and Bar - ‬6 min walk

About this property

SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/ Community 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.
***The full kitchen, dining and outdoor areas are available for all guests to enjoy.
***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...

Similar properties

An outdoor bar area with wooden tables and blue stools, a bar counter, and a sign that reads "Liqour Store".
Southwinds Motel
Old Town Key West
  • Pool
  • Breakfast included
  • Restaurant
  • Air conditioning
4.3 out of 5, Excellent, 1,394 reviews
The price is CA $169
CA $237 total
includes taxes & fees
Sep 7 - Sep 8
Southwinds Motel

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/ Community 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/ Community Pool?

As of Aug 27, 2026, prices found for a 1-night stay for 2 adults at SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/ Community Pool on Aug 31, 2026 start from CA $136, excluding 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/ Community 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/ Community 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/ Community 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/ Community 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/ Community Pool?

Check-in begins at 3:00 PM.

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

Free parking is not available at this guesthouse.

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

Yes, there's a heated pool.

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 38 out of 43 reviews
Rating 8 - Good. 4 out of 43 reviews
Rating 6 - Okay. 1 out of 43 reviews
Rating 4 - Poor. 0 out of 43 reviews
Rating 2 - Terrible. 0 out of 43 reviews

10/10

Cleanliness

10/10

Staff & service

7.4/10

Amenities

9.0/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Jason D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great little place with even better price!
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Beth M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay in Key West and the Inn on Fleming was delightful!
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

Sheila R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and very nice place
Stayed 3 nights in Feb 2026
Verified review

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
Verified review

10/10 Excellent

Christine R.

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

10/10 Excellent

Carlton F.

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

10/10 Excellent

Vince

Liked: Cleanliness, property conditions & facilities
Very clean room. Everything was great
Stayed 3 nights in Feb 2026
Verified review

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
From a partner site

10/10 Excellent

John A.

Great Stay in Key West

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: It was our first trip to Key West. The Inn on Fleming was a great find. Very nice property. Our room was as described and comfortable. Kitchen, common areas and pool were very nice. The concierge service was always available.
From a partner site

10/10 Excellent

Janice S.

Quaint and Charming Boutique Inn

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 on Flemington was exceptional from the check in process to the room and common areas. Our room was just as pictured on the web site. It was so conveniently located to the many attractions in the town and within walking distance to great restaurants. The staff was phenomenal and a special thanks to Hilary. She was great and such a pleasure to just sit and talk with!
Verified review

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
Verified review

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
Verified review

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
From a partner site

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
Verified review

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
Verified review

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
Verified review

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
From a partner site

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!
Verified review

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
Verified review

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
Verified review

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
From a partner site

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! :)
From a partner site

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.
Verified review

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
Verified review

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