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WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen Shared Heated Pool

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Welome to The Whitehead Room!
Plush linen
Enjoy a peaceful night's rest
Sink into your nighttime refuge
TV

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Pool
  • Free WiFi
  • Air conditioning
$258
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 Queen Bed

1 bathroom

Bathroom 1

Bathtub or shower · Toilet

Spaces

Deck or patio
Balcony
$258
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

  • Duval Street - 10 min walk - 0.9 km
  • Mallory Square - 15 min walk - 1.3 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 - 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

WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen 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 Whitehead Room is located on the 2nd floor and offers a queen bed. Enjoy your privacy in this location that is accessible from the back deck with lounge furnishings. Dade County pine walls and a PRIVATE bathroom with a tub/shower combination complete the cozy space. This room connects to the Truman Room.

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
default

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 WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen 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 WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen Shared Heated Pool?

As of Apr 23, 2026, prices found for a 1-night stay for 2 adults at WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen Shared Heated Pool on Jul 15, 2026 start from $258, 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 WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen Shared Heated Pool pet-friendly?

No, pets are not allowed at this property.

What time is check-in at WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen Shared Heated Pool?

Check-in begins at 3:00 PM.

What time is check-out at WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen Shared Heated Pool?

Check-out is at 11:00 AM.

Where is WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen 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).

WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen 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. 23 out of 26 reviews
Rating 8 - Good. 2 out of 26 reviews
Rating 6 - Okay. 1 out of 26 reviews
Rating 4 - Poor. 0 out of 26 reviews
Rating 2 - Terrible. 0 out of 26 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Gayla P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was very responsive and property was outstanding!
Stayed 4 nights in Nov 2025
Verified

10/10 Excellent

Michael M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was great. Communication was excellent. Easy checkin/checkout process. Great experience
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Erika D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cozy room, nice pool, wonderful property overall.
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Luc A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was perfect and location is i
Stayed 4 nights in Dec 2025
From a partner site

10/10 Excellent

Carol W.

Charming Home converted to an Inn

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 location was perfect in a quiet neighborhood. We could walk everywhere. Bikes were available to rent at the Inn. The front porch was a great place to hang out after wander around town. The communication with was great. We will be back,
Verified

10/10 Excellent

James

Liked: Cleanliness, amenities, property conditions & facilities
Complete Beautiful arrangement
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Loretta C.

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

Very nice & well located accommodations

Great time staying there
Stayed 2 nights in Jan 2025
From a partner site

10/10 Excellent

jamie r.

Perfect place to 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 recommend this vacation rental. Reviewer Comments: Perfect location. Everyone was really nice.
Verified

10/10 Excellent

Gloria B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Super property with little pool and quiet neighborhood. Very Key Westy.
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

PAM M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The room was very clean. The AC and ceiling fans were effective, so we had no problem with the temperature in the room. The shopping was walkable, and we had breakfast options within a few blocks. The only drawback was parking close by.
Stayed 4 nights in Nov 2025
Verified

10/10 Excellent

James N.

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

Dope Little Spot

Cozy little room with all the amenities!
Stayed 3 nights in Jul 2025
From a partner site

10/10 Excellent

Karley S.

So cute and cozy

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 loved our experience in the Whitehead room. Everything was very clean and the space was so comfy and cozy. Will definitely be staying at this property again. The self check in was easy and responses with questions were quick.
From a partner site

10/10 Excellent

Joshua T.

Therapy vacation

Rating Details: The property manager was very helpful. The vacation rental was very clean. 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 enjoyed our stay and cleaned.
Verified

10/10 Excellent

Jessica C.

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

Perfect Key West Getaway!

We had a fantastic stay at The Inn on Fleming! The location is ideal—quiet enough to relax, yet just a short bike ride to Duval Street and all the Key West action. The inn itself is charming, well-maintained, and has a lovely historic feel with modern amenities.Our room was clean, cozy, and tastefully decorated, with a comfortable bed and great air conditioning (a must in Key West!). Highly recommend The Inn on Fleming for couples or families looking for a relaxing and authentic Key West experience!
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Ulises

Liked: Cleanliness, property conditions & facilities, communication
Very good
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Philip M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a last min. trip / deal. Great spot, just a few blocks from Duval. Grocery store and great breakfast place a few blocks away on Flemming. Sunny Eggs, I ate there 2 mornings in a row. Rent a bike for 10 a day and cruise all over the island. Staff was ready to help with any questions. Clean, cold AC, hot water. Small pool to hang out in away from the noise. I will stay here again!Phil
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Mariana O.

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

Perfect location

Beautiful stately home, historic feeling, but remodeled with all modern conveniences. Loved the continental breakfast and complementary wine selection at night. We got back from walking to find a cold beer in the fridge, a little snack and thoroughly enjoyed the quiet neighborhood. Loved the porch at night. So peaceful!
Stayed 3 nights in Jan 2025
From a partner site

10/10 Excellent

A guest from Cleveland , TN

Honeymoon 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: The Inn on Fleming was charming. My husband and I really enjoyed our stay. The Inn was very clean, stocked well and extremely comfortable. It was close to all the places we wanted to go and we were able to park close with no issue. We will definitely be back.
From a partner site

8/10 Good

William E.

South Floridian visit

Rating Details: 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: We had stayed here before and will again. It is quiet and nice. Getting extra supplies was difficult as there is no staff there most of the day. But things were maintained well and communication was very good.
Verified

8/10 Good

Diana J.

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

Bathroom need work

The picture you have is the first impression when you enter the room. Small and stylishly decorated. The bathroom was rough. The grout was ugly and pieces cracked and hurt your feet, The bathroom window, right in front of your face every time you used the sink was dirty, not just the glass but the minions were filthy. The flush valve on the toilet was broken and leaked. Fix that and it would be an awesome place. As I said before, the common areas were lovely, all furnishings were tasteful, kitchen was well stocked. We liked the location.
Stayed 3 nights in Jan 2025
From a partner site

6/10 Okay

paul p.

interesting

Rating Details: The property manager was adequately helpful. The vacation rental was somewhat dirty. I was happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Was not sure what to expect. Pricing to me is crazy in this town. I found a place that was the cheapest in town available. The pictures they display always look great. So to be frank the house is old like most in this town, very old nothing of the bones have been changed so the doors don't close right, windows painted shut. All original with a few exceptions. Main common area beautifully redone and kept, the outside common area is great as well. So my only complaint was the floor was filthy. I spilled some water when I wiped it up the towel was black. So when they clean, they don't was the hardwood floor. Remember this is an old beach town with high priced rent. One last thing there was a distinct smell
Verified

10/10 Excellent

Christine B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved relaxing on the various porches, decks and pool at this beautiful property, as well as in our comfortable room. Thoughtful touches included filtered water, plenty of towels, assortment of coffees, in-room ice-maker. Quiet neighborhood that is very walkable to marina and Duvall St, as well as excellent nearby bakery, Cuban coffee shop and restaurants.
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

Julie Caroline R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Chambre parfaite! Cuisine parfaite à notre disposition. Rien ne manque! Merci!
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Gerard L.

Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Mary Jo B.

Stayed 2 nights in Nov 2025