Bed and Breakfast in Key West, FL
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this bed and breakfast
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...
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...
Amenities at SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/ Community Pool
Non-smoking
No pets allowed
Map of Key West, FL
Ratings and reviews
10 / 10Outstanding·Feb 2026
Very clean room. Everything was great
10 / 10Outstanding·Feb 2026
Great location and very nice place
10 / 10Outstanding·Feb 2026
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!
6 / 10Average·Jan 2026
Rating Details:
The property manager was more than helpful.
The vacation rental was spotless.
I was very happy with the location.
I was somewhat dissatisfied with the condition of the vacation rental.
Overall, I do not recommend this vacation rental.
Reviewer Comments:
We discovered this property last year and had such a great experience we booked again this year. The Inn was clean in the common areas and when we arrived. However, trash was not collected at any time during our stay, towels were not refreshed, dehumidifier stopped minutes after we arrived and was not remedied. Our previous stay, a selection of muffins and fruit in the AM, a choice of wine in the evening and the service of our rooms made the stay special. None of those amenities were offered this year. 2 other guest were told they could prepare a meal, only to find microwave the only source to prepare their food. Location is awesome, just a bit spare on service and amenities. Easy walk to anything you might want to see and do.
$$$$
Top rated by guests
9.6Outstanding
(35 Ratings)
"Very clean room. Everything was great "
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