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FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool

Guest house near Duval Street in Key West

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Photo gallery for FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor 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

10 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

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  • Pool
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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
  • ‪Half Shell Raw Bar - ‬8 min walk
  • ‪Pepe's Cafe - ‬7 min walk

About this property

FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor 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 Flagler Room, located on the first floor, is a delightful place to decompress at the end of a fun day. Enjoy your slumber on your king bed, savor a cup of keurig coffee, and enjoy a show on the flat screen TV. This room also offers a PRIVATE wheel-in shower for easy access.

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

Building design
The Southernmost Inn - Adults Only
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  • Pool
  • Hot tub
  • Breakfast included
  • Air conditioning
4.2 out of 5, Very good, 1,435 reviews
The price is CA $92
CA $166 total
includes taxes & fees
Sep 8 - Sep 9
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Property amenities

Internet

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

Things to do

  • Billiards/pool table
  • Communal pool
  • Heated pool
  • Tennis

Room amenities

Entertainment

  • Smart TV with cable/satellite channels

Bedroom

  • Bedsheets provided

Bathroom

  • Hair dryer
  • Shower
  • 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

2731-256378

Frequently asked questions

How close is FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor 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 FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool?

As of Sept 6, 2026, prices found for a 1-night stay for 2 adults at FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool on Sept 7, 2026 start from CA $123, 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 FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool have an airport shuttle?

Airport shuttle services are not available at this guesthouse.

How close is FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor 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 FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool offer free breakfast?

This guesthouse does not offer free breakfast.

Is there a casino at FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool?

No, there is no casino at this guesthouse.

What time is check-in at FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool?

Check-in begins at 3:00 PM.

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

Free parking is not available at this guesthouse.

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

Yes, there's a heated pool.

Does FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool have a spa?

There are no spa services available at this guesthouse.

How close is FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool to downtown Key West?

This guesthouse is 0.5 mi away from Key West.

FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 43 out of 45 reviews
Rating 8 - Good. 1 out of 45 reviews
Rating 6 - Okay. 0 out of 45 reviews
Rating 4 - Poor. 1 out of 45 reviews
Rating 2 - Terrible. 0 out of 45 reviews

10/10

Cleanliness

10/10

Staff & service

9.6/10

Amenities

9.8/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Cheryl D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay. The property was spotless, peaceful, and exactly what we needed for a relaxing trip. It’s in a quiet area but still a fairly easy, enjoyable walk to Duval Street. Would definitely stay here again.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Luca

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean room | Staff very responsive | Shops nearby
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Kaurie P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely place, clean and comfortable in a perfect location!
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Scott S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Giedrius Tomas B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed the fengshui of the place. The staff was peofessional and not intrusive
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Stephanie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The Inn on Fleming was very comfortable and relaxing. The Flagler Room is lovely and large. The kitchen is very nice and we used it often. Staff was very accommodating to all of our needs. The only issue is with parking. The text you receive with parking instructions goes to your spam text folder. We didn’t see the spam text and received an expensive ticket for overnight parking on the street. We finally figured out where to park and found a lot not too far away. Other than this expensive lesson and extreme frustration, we had a good time. Thank you.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Mike A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This place was great. Convenient to everything.
Stayed 11 nights in Nov 2025
Verified review

10/10 Excellent

john l.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property.and location
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

PaulMMurphy

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful inn in a very good location. Short walk to the ferry terminal for the day trip to the Dry Tortugas.
Stayed 7 nights in Sep 2025
Verified review

10/10 Excellent

Linda P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stat was wonderful. The room was exactly like the pictur and the extra amenities were so nice. Loved the location. Very quiet and convient
Stayed 4 nights in Dec 2025
From a partner site

10/10 Excellent

Amy J.

Amazing location

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: This was a beautiful area in Key West, the room and surrounding areas in the house were beautiful and clean.
Verified review

10/10 Excellent

NATALIE

Liked: Cleanliness, amenities, property conditions & facilities, communication
We enjoyed our stay. We love the area and were able to walk to all areas of old town.
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

patrick d.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean place! Outstanding!Great location, and quiet at night..I"ll be back for sure! PatrickRochester, NY
Stayed 2 nights in Jan 2026
Verified review

10/10 Excellent

Natalie K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very relaxing room with wonderful attention to detail. I particularly loved the the provided pitchers that work very well for having both hot and cold filtered water in the room. Being on the main floor was so convenient! I enjoyed sitting on the front porch, listening to the waterfall on the back patio, as well walking to the massage place just down the street. I loved the longer walks to the marina, Fausto’s grocery store, Duval St, Hemingway House, and the southernmost point. Thank you!
Stayed 4 nights in Mar 2026
From a partner site

10/10 Excellent

Frederick R.

Good times at the Flagler 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: Although we stayed only four nights, wishing we would’ve stayed longer impressed with the cleanliness of the entire house and our room. Everything you need for a short stay. location was also great restaurants, and groceries all within walking distance.
Verified review

10/10 Excellent

Lauren

Liked: Cleanliness, amenities, property conditions & facilities, communication
Enjoyed the stay. Very cute, nice house. Friendly staff. Clean and comfortable bed. Walking distance to Duval. Would definitely stay there again.
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Gerald T.

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

Southern Charm

We had a nice large room, and bed. It is located close to shops, and nightlife, on a quiet street perfect for chilling on the large porch with comfy chairs. Would stay again.
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

Cheryl

Liked: Cleanliness, amenities, property conditions & facilities, communication
We loved it! Our room was spacious, had a mini fridge and our own icemaker. The shared kitchen had all the necessities and then some. The owners have gone above and beyond to anticipate everything that a traveler would need. Will definitely stay here again.
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Albert Y.

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

Key West

Excellent
Stayed 2 nights in Jun 2025
Verified review

10/10 Excellent

Christopher B.

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

Great stay!

We really enjoyed staying here! The location is within feat. From a Duval loop bus stop, which made it really easy to get around without a car. Our rental car rarely left the parking spot on the street.
Stayed 4 nights in May 2025
From a partner site

10/10 Excellent

James D.

Wonderful stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We very much enjoyed our stay. Everything was just as described.
Verified review

10/10 Excellent

Mark K.

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

A Good Find

Very nice accommodations. The room was clean and comfortable, and communications were prompt. Price was reasonable for a last-minute Saturday night booking.
Stayed 1 night in Feb 2025
From a partner site

10/10 Excellent

Lauren S.

Loved it!

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: Very cute house. Clean. Perfect location. Had a great time and would definitely stay there again.
From a partner site

10/10 Excellent

Denise F.

Great room, great 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: We loved the room & the house. Clean, well maintained, and well appointed. Great part of town & convenient to get anywhere.
From a partner site

10/10 Excellent

A guest from Somerville, MA

Beautiful, comfortable room and excellent location

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 Fleming Street was an amazing place to stay during our terrific Key West winter vacation. The room was spacious, clean, and comfortable. I loved the shared kitchen and dining space. I began almost every morning lounging by the pool with a complimentary coffee. Great way to begin the day. The location was perfect, a couple blocks from yummy breakfast places and a short walk from the action on Duvall Street. Also loved being close to a well-stocked grocery store (that also sells beer and wine). Our stay could not have been more perfect. And, the concierge service was incredibly helpful with excursion reservations including jet ski and jeep rental.