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 ecotours and cycling.
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
The Breakfast Club, Too - 12 min walk
Frequently asked questions
Does FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community 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/Community Pool?
As of Oct 23, 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 Oct 25, 2026 start from $262, 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/Community 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/Community 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/Community Pool?
Check-out is at 11:00 AM.
Where is FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool located?
Located in Old Town Key West, this guesthouse is within a 10-minute walk of Key West Theater and Duval Street. Florida Keys Beaches and Mallory Square are also within 1 mi (2 km).
FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool Reviews
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
We enjoyed out stay. The property was very pleasant and well situated in the old town of Key West. We were within walking distance of all the main sites.
My first of what I hope to be many more trips to Key West was absolutely wonderful. We stayed in The Flagler Room at the Inn on Fleming. Such a nice place, so charming, very clean, well equipped, great location, o & easy check in/check out process! We didn’t want to leave. We loved it! I will definitely book again!
Stayed 2 nights in Oct 2026
From a partner site
10/10 Excellent
Candee B.
Oct 15, 2026
Very comfortable!
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:
Great room! Could use a few more plugs and the phone power strip did not seem to work. But loved the house and back yard area!
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.
This place was so charming and centrally located to all cool things to do in Key West. Even found an amazing local place right down the street for nightcaps. Even found a free parking spot! Love the adults only aspect. Made for a relaxing and fun filled trip. Host contact was great and very responsive. Loved the big fridge in the room too although there was also a full fridge out in the kitchen area. Though there was no cooking availability so I think that might be the only thing I expected but everything else was fantastic. Highly recommend 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:
The property was clean, comfortable, quiet and convenient. The concierge service was an added bonus.
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
From a partner site
10/10 Excellent
Amy J.
Feb 23, 2026
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.
Very clean place! Outstanding!Great location, and quiet at night..I"ll be back for sure! PatrickRochester, NY
Stayed 2 nights in Jan 2026
From a partner site
10/10 Excellent
Stephanie R.
Jul 13, 2026
Relaxing & Enjoyable
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 an absolutely wonderful time while staying at the Inn on Fleming. The Flagler Room is large, lovely and on the 1st floor. The management company was very attentive to any needs we had. The location is ideal as we walked everywhere we wanted to go. The only issue is with parking. The text with parking instructions goes to your spam text which we missed and therefore got an expensive parking ticket for parking in an empty spot on the street overnight. We finally figured out how to find a parking lot where we could legally park. Other than this expensive lesson, we had a great time.
From a partner site
10/10 Excellent
Frederick R.
Feb 21, 2026
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.
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
Verified review
10/10 Excellent
Lauren
Aug 18, 2025
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.
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
Oct 26, 2025
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.