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

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

Spacious suite
Cozy bedding
Cheery surroundings
Enjoy a peaceful slumber
Countertop ice machine and keurig

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Heated Pool
  • Free WiFi
  • Balcony
  • Air conditioning
  • Balcony or patio
  • Refrigerator
$241
avg per night

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪10 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.)
    ‪12 min drive‬

Rooms & beds

1 bedroom (sleeps 2)

Bedroom 1

1 King Bed

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Balcony
Garden
$241
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 Florida Keys Beaches and Fort Zachary Taylor Historic State Park. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting. Discover the area's water adventures with scuba diving and snorkeling nearby, or enjoy the great outdoors with cycling and ecotours.
View more Guest Houses in Key WestOpens in a new window

What's nearby

  • Studios of Key West - 3 min walk - 0.3 km
  • Duval Street - 9 min walk - 0.8 km
  • Ernest Hemingway Home and Museum - 14 min walk - 1.2 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

  • ‪Cuban Coffee Queen Waterfront - ‬7 min walk
  • ‪Schooner Wharf Bar - ‬10 min walk
  • ‪Kermit's Key West Key Lime Shoppe - ‬11 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/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 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...
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 FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor 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 FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Shared Heated Pool?

As of Apr 22, 2026, prices found for a 1-night stay for 2 adults at FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Shared Heated Pool on Jul 6, 2026 start from $241, 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 FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Shared Heated Pool pet-friendly?

No, pets are not allowed at this property.

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

Check-in begins at 3:00 PM.

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

Check-out is at 11:00 AM.

Where is FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor 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).

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

Reviews

9.8

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. 35 out of 37 reviews
Rating 8 - Good. 1 out of 37 reviews
Rating 6 - Okay. 0 out of 37 reviews
Rating 4 - Poor. 1 out of 37 reviews
Rating 2 - Terrible. 0 out of 37 reviews

10/10

Cleanliness

9.6/10

Amenities

9.6/10

Property conditions & facilities

10/10

Check-in

9.8/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

Reviews

Verified

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

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

10/10 Excellent

Scott S.

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

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

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

10/10 Excellent

john l.

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

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

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

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

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

10/10 Excellent

Cecelia W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The room was immaculately clean, the bed was very comfortable. We did ask for an additional blanket which was delivered immediately. We stayed in the Flagler Room which is downstairs. I don't know how many other guests were there but we only heard footsteps a couple of times so it was very quiet. The location was off the main strip far enough to be a quiet street but we still walked most everywhere we needed to go and only got an uber a couple of times. Would definitely stay again.
Stayed 6 nights in Nov 2025
Verified

10/10 Excellent

Albert Y.

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

Key West

Excellent
Stayed 2 nights in Jun 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.
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.
Verified

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

Darren S.

Great time at the INN on Flemming

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 had a great time, the room was nice, clean and comfortable. coffee in the morning on the front porch was nice. the location was great. the only issue was parking but that really wasnt an issue since we didnt drive our car the whole time we were there.
Verified

10/10 Excellent

Amy H.

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

First Timers

This trip to Key West was a first for both myself and my husband. The Inn on Fleming and its amenities made it all the better. The Flagler room was spacious, clean, and comfortable. The common areas were well stocked and easily accessible to all.
Stayed 4 nights in Jun 2025
Verified

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

Brent H.

July 18-21

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The Inn was very clean and welcoming. The room was perfect and comfortable. The pool , although small was very relaxing. We would stay at the Inn on Fleming again.
From a partner site

10/10 Excellent

Janet E.

Quiet and comfortable

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 place, easy to get around, clean, lovely sitting areas. Enjoyed the ease of light breakfast and a sip of wine in the evening.
Verified

8/10 Good

Barbara

Liked: Cleanliness, amenities, property conditions & facilities
Great location and a lovely restored home. The common area was fabulous, with a full kitchen, eating/gathering area, and a small plunge pool. Room was nice but needed a few repairs. Bathroom vanity was worn and needs replacing. The appearance of some small bugs was disturbing but quickly addressed. Overall a nice place to stay.
Stayed 4 nights in May 2025
From a partner site

10/10 Excellent

Constance P.

Nice 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: Inn on the Fleming had a good location with a health food store and restaurant 2 blocks away. Great location. We were able to walk or take the trolley to most attractions. We arrived early and if the room is ready they will let you know and you can get in early which was really nice. Room and house were clean, house was beautiful, kitchen area nice. Bed was A little soft for me but not bad. We did the Yankee Freedom Ferry and could walk there.