Verified
10/10 Excellent
Michael S.
17 Apr 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Stay
Michael S.
Stayed 7 nights in Dec 2023
Entire home
Hemingway Hideaway in the Truman Annex
Photo gallery for Hemingway Hideaway in the Truman Annex
Experience the charm of Key West at Hemingway Hideaway in Truman Annex, a delightful 3-story townhome within walking distance to everything. With an open floor plan and modern amenities, this home is perfect for your holiday getaway. Enjoy the private pool shared by the Foundry building or take a short stroll to Fort Zachary Taylor and Historic Seaport / Mallory Square.
Reviews
9.89.8 out of 10
Exceptional
Entire home
2 bedrooms3 bathroomsSleeps 61527 sq ft
Popular amenities
- Pool
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
- Air-conditioning
Add dates for prices
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Hemingway Hideaway in the Truman Annex
Hemingway Hideaway – Charming Townhouse in Truman Annex at Historic Foundry Building
Discover your perfect Key West retreat in this beautifully positioned 3-story townhouse within the coveted Truman Annex community. Just steps away from the vibrant heart of Key West, Hemingway Hideaway offers the ideal blend of comfort, convenience, and classic island charm.
Property Highlights:
Gated Entry & Private Courtyard: Enjoy privacy and tranquility as you enter your own peaceful oasis.
Open Floor Plan: The spacious first floor seamlessly connects the living room, dining area, and fully equipped kitchen — perfect for relaxing or entertaining.
Half Bath/Powder Room: Conveniently located off the kitchen.
Master Suite on Second Floor: King-size bed, ensuite bathroom, two linen closets, in-unit washer/dryer, and a private balcony for morning coffee or evening relaxation.
Third Floor Bedroom: Queen-size bed occupies the entire level with its own ensuite bathroom.
Designated Parking: One assigned parking space located at the rear of the unit.
Private Pool: Enjoy access to the Foundry building’s exclusive pool — a refreshing escape after a day exploring.
Complimentary Bicycles: Two bikes included to effortlessly explore Key West like a local.
Prime Location:
Just steps from the Truman Amphitheater & Splash Park, Fort Zachary Taylor, the Historic Seaport & Mallory Square, Truman’s Little White House, and popular spots like the Green Parrot. Within a 4-block radius of the lively 200 block of Duval Street — where all the action happens!
Booking Notes:
Hemingway Hideaway – Charming Townhouse in Truman Annex at Historic Foundry Building
Discover your perfect Key West retreat in this beautifully positioned 3-story townhouse within the coveted Truman Annex community. Just steps away from the vibrant heart of Key West, Hemingway Hideaway offers the ideal blend of comfort, convenience, and classic island charm.
Property Highlights:
Gated Entry & Private Courtyard: Enjoy privacy and tranquility as you enter your own peaceful oasis.
Open Floor Plan: The spacious first floor seamlessly connects the living room, dining area, and fully equipped kitchen — perfect for relaxing or entertaining.
Half Bath/Powder Room: Conveniently located off the kitchen.
Master Suite on Second Floor: King-size bed, ensuite bathroom, two linen closets, in-unit washer/dryer, and a private balcony for morning coffee or evening relaxation.
Third Floor Bedroom: Queen-size bed occupies the entire level with its own ensuite bathroom.
Designated Parking: One assigned parking space located at the rear of the unit.
Private Pool: Enjoy access to the Foundry building’s exclusive pool — a refreshing escape after a day exploring.
Complimentary Bicycles: Two bikes included to effortlessly explore Key West like a local.
Prime Location:
Just steps from the Truman Amphitheater & Splash Park, Fort Zachary Taylor, the Historic Seaport & Mallory Square, Truman’s Little White House, and popular spots like the Green Parrot. Within a 4-block radius of the lively 200 block of Duval Street — where all the action happens!
Booking Notes:
Minimum 7-night stay required between January 1 – April 30, 2020, with Saturday-to-Saturday check-in/check-out.
Outside this period, flexible arrival and departure days.
Discounts available for stays of 28 nights or longer.
If this property is booked, we can recommend other great homes in the area.
Pack your suitcase and get ready for an unforgettable Key West getaway in your home away from home!
Outside this period, flexible arrival and departure days.
Discounts available for multiple months stays
If this property is booked, we can recommend other great homes in the area.
Pack your suitcase and get ready for an unforgettable Key West getaway in your home away from home!
Discover your perfect Key West retreat in this beautifully positioned 3-story townhouse within the coveted Truman Annex community. Just steps away from the vibrant heart of Key West, Hemingway Hideaway offers the ideal blend of comfort, convenience, and classic island charm.
Property Highlights:
Gated Entry & Private Courtyard: Enjoy privacy and tranquility as you enter your own peaceful oasis.
Open Floor Plan: The spacious first floor seamlessly connects the living room, dining area, and fully equipped kitchen — perfect for relaxing or entertaining.
Half Bath/Powder Room: Conveniently located off the kitchen.
Master Suite on Second Floor: King-size bed, ensuite bathroom, two linen closets, in-unit washer/dryer, and a private balcony for morning coffee or evening relaxation.
Third Floor Bedroom: Queen-size bed occupies the entire level with its own ensuite bathroom.
Designated Parking: One assigned parking space located at the rear of the unit.
Private Pool: Enjoy access to the Foundry building’s exclusive pool — a refreshing escape after a day exploring.
Complimentary Bicycles: Two bikes included to effortlessly explore Key West like a local.
Prime Location:
Just steps from the Truman Amphitheater & Splash Park, Fort Zachary Taylor, the Historic Seaport & Mallory Square, Truman’s Little White House, and popular spots like the Green Parrot. Within a 4-block radius of the lively 200 block of Duval Street — where all the action happens!
Booking Notes:
Hemingway Hideaway – Charming Townhouse in Truman Annex at Historic Foundry Building
Discover your perfect Key West retreat in this beautifully positioned 3-story townhouse within the coveted Truman Annex community. Just steps away from the vibrant heart of Key West, Hemingway Hideaway offers the ideal blend of comfort, convenience, and classic island charm.
Property Highlights:
Gated Entry & Private Courtyard: Enjoy privacy and tranquility as you enter your own peaceful oasis.
Open Floor Plan: The spacious first floor seamlessly connects the living room, dining area, and fully equipped kitchen — perfect for relaxing or entertaining.
Half Bath/Powder Room: Conveniently located off the kitchen.
Master Suite on Second Floor: King-size bed, ensuite bathroom, two linen closets, in-unit washer/dryer, and a private balcony for morning coffee or evening relaxation.
Third Floor Bedroom: Queen-size bed occupies the entire level with its own ensuite bathroom.
Designated Parking: One assigned parking space located at the rear of the unit.
Private Pool: Enjoy access to the Foundry building’s exclusive pool — a refreshing escape after a day exploring.
Complimentary Bicycles: Two bikes included to effortlessly explore Key West like a local.
Prime Location:
Just steps from the Truman Amphitheater & Splash Park, Fort Zachary Taylor, the Historic Seaport & Mallory Square, Truman’s Little White House, and popular spots like the Green Parrot. Within a 4-block radius of the lively 200 block of Duval Street — where all the action happens!
Booking Notes:
Minimum 7-night stay required between January 1 – April 30, 2020, with Saturday-to-Saturday check-in/check-out.
Outside this period, flexible arrival and departure days.
Discounts available for stays of 28 nights or longer.
If this property is booked, we can recommend other great homes in the area.
Pack your suitcase and get ready for an unforgettable Key West getaway in your home away from home!
Outside this period, flexible arrival and departure days.
Discounts available for multiple months stays
If this property is booked, we can recommend other great homes in the area.
Pack your suitcase and get ready for an unforgettable Key West getaway in your home away from home!
Property amenities
Pool/Spa
- Communal pool
- Private pool
Internet
- Available in the house: Free WiFi
Parking and transport
- Car not required
- Parking on site
Kitchen
- Blender
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dishwasher
- Hob
- Microwave
- Oven
- Refrigerator
- Toaster
Bedrooms
- 2 bedrooms
- Bedsheets provided
- Sofa bed
Bathroom
- 2.5 bathrooms
- Bathtub or shower
- Hair dryer
- Shower
- Towels provided
Entertainment
- TV with cable/satellite channels
Outdoor areas
- Balcony
Laundry
- Laundry facilities
- Washing machine
Comfort
- Air conditioning
- Heating
Pets
- No pets allowed
Suitability/Accessibility
- No lift
- Smoke-free property
Services and conveniences
- Iron/ironing board
Location highlights
- In the city centre
- Near a health/beauty spa
Things to do
- Birdwatching nearby
- Cycling nearby
- Ecotours nearby
- Fishing nearby
- Golfing nearby
- Jet skiing nearby
- Kayaking nearby
- Motor boating nearby
- Parasailing nearby
- Sailing nearby
- Scuba diving nearby
- Snorkelling nearby
- Swimming nearby
Safety features
- Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
- Smoke detector (host has indicated there is a smoke detector on the property)
- First aid kit
- Fire extinguisher
- Deadbolt lock
General
- Unit size: 1,527 square feet
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Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age - 28
Check-out
Check-out before 10:00 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
Pets not allowed
Children and extra beds
Children are welcome
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that 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
We should mention
This property does not have any lifts
A car is not required for transport to and from this property
About the area
Located in Old Town Key West, a neighbourhood in Key West, this holiday home is near a water park. 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. USCGC Ingham Maritime Museum and Mel Fisher Maritime Museum are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and ecotours. Visit our Key West travel guide
View more Holiday homes in Key West
Key West, FL
What's nearby
Harry S. Truman Little White House2 min walk - 0.2 km
Duval Street4 min walk - 0.4 km
Mallory Square8 min walk - 0.7 km
Ernest Hemingway Home and Museum11 min walk - 0.9 km- Florida Keys National Marine Sanctuary9 min walk - 0.8 km
Getting around
- Key West, FL (EYW-Key West Intl.)14 min drive
Restaurants
- Key Lime Pie Factory5 min walk
- The Bull & Whistle Bar5 min walk
- Fogarty's and Flying Monkey's5 min walk
- Cuban Coffee Queen5 min walk
- La Concha Bar5 min walk
Frequently asked questions
Does Hemingway Hideaway in the Truman Annex have a pool?
Yes, this property has a pool.
Is Hemingway Hideaway in the Truman Annex pet-friendly?
No, pets are not allowed at this property.
How much is parking at Hemingway Hideaway in the Truman Annex?
On-site parking is available at the property.
What time is check-in at Hemingway Hideaway in the Truman Annex?
Check-in begins at 4:00 PM.
What time is check-out at Hemingway Hideaway in the Truman Annex?
Checkout is at 10:00 AM.
Where is Hemingway Hideaway in the Truman Annex located?
Located in Old Town Key West, this holiday home is within a 5-minute walk of Harry S. Truman Little White House and Duval Street. Florida Keys Beaches and Mallory Square are also within 10 minutes.
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Hemingway Hideaway in the Truman Annex Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new windowRating 10 - Excellent. 61 out of 68 reviews
10 - Excellent
61
Rating 8 - Good. 5 out of 68 reviews
8 - Good
5
Rating 6 - Okay. 2 out of 68 reviews
6 - Okay
2
Rating 4 - Poor. 0 out of 68 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 68 reviews
2 - Terrible
0
10
Cleanliness
9.8
Location
Reviews
Verified
10/10 Excellent
roberta i.
25 Feb 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Pleasant stay in a great neighborhood
Our daughter and family enjoyed staying here--lots of space, a nice kitchen, a good neighborhood.
roberta i.
Stayed 7 nights in Feb 2024
Verified
10/10 Excellent
Teresa B.
19 Mar 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Spring getaway
Great location, we walked or rode our bikes everywhere.
Teresa B.
Stayed 7 nights in Feb 2024
Verified
10/10 Excellent
Donald G.
29 Jan 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
January 2025 stay
A very nice property in a great location!
Donald G.
Stayed 7 nights in Jan 2025
Verified
10/10 Excellent
Mary E.
31 May 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
A Great Place to Stay in Key West!!
We stayed for a wonderful week, and found the property not only beautiful, it was super comfy! We loved the privacy and the gated community, and we also loved how close the home was to downtown and to Mallory Square. Would definitely book again!
Mary E.
Stayed 7 nights in May 2024
Verified
10/10 Excellent
Debbie M.
7 Jan 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing stay in the Annex
This place was perfect! Plenty of room for my husband and daughter and son in law. Private and beautiful but within walking distance to everything. Hoping to be back next year!
Debbie M.
Stayed 7 nights in Dec 2024
Verified
10/10 Excellent
Rachel S.
5 Apr 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice property!
This home is well appointed and conveniently located within walking distance to restaurants and shopping.
We would rent again if the price stays consistent with our previous booking.
Rachel S.
Stayed 9 nights in Aug 2023
Verified
10/10 Excellent
Matt H.
26 Jan 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Will be back!
The weather was not on our side this year but the place was very nice and ow er was very responsive. Close to several restaurants and ice cream!
Matt H.
Stayed 7 nights in Jan 2025
Verified
10/10 Excellent
Mary N.
21 Feb 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect
Great location. Super clean. Nicely furnished. Had everything we needed. Walking distance to all things in Key West. This was our 3rd visit to Key West and the best place we have stayed. Hope to be back next year.
Mary N.
Stayed 7 nights in Feb 2025
Verified
10/10 Excellent
Susie D.
1 Nov 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Best Property in The Foundry
We have been visiting Key West for 25+ years and our fav place to stay is in the Foundry in Truman Annex. It's close to everything on Duvall but far enough away to enjoy complete peace and quiet. This unit was by far the best we've stayed in! Spotless clean, updated, well decorated, and had everything we needed.
Would highly recommend!
Susie D.
Stayed 9 nights in Oct 2023
Verified
10/10 Excellent
Ellen V.
17 Aug 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
August Vacation in Key West
We absolutely loved this vacation home. Very comfortable and no complaints. It was beautiful and very easy to get around the neighborhood. We loved everything about the condo. thank you for a lovely place to vacation we will be visiting again and hope to stay in this same home.
Ellen V.
Stayed 7 nights in Aug 2024
Verified
10/10 Excellent
Brice C.
6 Apr 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
So relaxing
We stayed for a week over Christmas 2023. (Our second time staying there!) Had a wonderfully relaxing time. The property was perfect for the 4 of us in the family. Very clean, comfortable, and of course the location can’t be beat. Thank you!
Brice C.
Stayed 7 nights in Dec 2023
Verified
10/10 Excellent
Paul L.
28 Oct 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location. Extremely safe. Short walk to all the action
We stayed at the Truman Annex and loved it. So close to everything. Very quiet location. Security gates. Was great. Only issue is there is nowhere to park your scooter if you rent one in addition to having your own car. We already booked for 2025!
Paul L.
Stayed 10 nights in Oct 2024
Verified
10/10 Excellent
Tonja M.
20 Aug 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome location!
Truman Annex is an awesome location. Secure, quiet, and really pretty Close to everything. You can walk or ride bikes to anywhere you want to go. The unit is lovely and the bikes provided are a bonus. We rode them every day. Definitely recommend this property.
Tonja M.
Stayed 7 nights in Aug 2023
Verified
10/10 Excellent
Jill K.
30 Mar 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent experience
Perfect location, near it all! Appreciate the beach towels and 4 beach chairs! Had a great stay! Even when lost on way in - emailed and heard back right away from mgmt. make sure you get solid directions to parking spot prior (Emma street turns into front street). That’s a tip I wish I knew before! Regardless I would stay here again!
Jill K.
Stayed 7 nights in Mar 2024
Verified
8/10 Good
Melodye P.
7 Mar 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Pretty Rental in a Great Location
Lovely townhouse in a great location. Only negatives - bad directions to property (one street turned into noted street) and insufficient dishware and forks. Lack of blender which was rectified after we were told there were no blenders in Key West and we found one at Ace Hardware. All minor inconveniences and we had a nice time.
Melodye P.
Stayed 7 nights in Feb 2025
Verified
10/10 Excellent
Carolyn S.
10 Nov 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay at Hemingway Hideaway! We were close to everything and the home is very clean and comfortable.
Carolyn S.
Stayed 7 nights in Nov 2025
Verified
10/10 Excellent
Verified traveller
19 Nov 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was ideal for us. Clean, super comfy, great location.
Verified traveller
Stayed 7 nights in Nov 2025
Verified
10/10 Excellent
Ryck S.
12 Apr 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Week @ Hemmingway Hideaway!
Loved everything about this property!
Ryck S.
Stayed 7 nights in Apr 2025
Verified
10/10 Excellent
Katie H.
17 Apr 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Hemingway Hideaway
The house is beautiful, very well appointed and in an amazing location. We would definitely stay there again!
Katie H.
Stayed 7 nights in Apr 2023
Verified
10/10 Excellent
Mitzi C.
22 Apr 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Key West
Great Location
Mitzi C.
Stayed 7 nights in Apr 2024
Verified
10/10 Excellent
Stephen D.
13 Apr 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Truman Annex
Have stayed at various locations in the Truman Annex with friends and found this one the best yet. Had a couple of very minor issues that were addressed immediately. Would highly recommend this property.
Stephen D.
Stayed 7 nights in Apr 2024
Verified
10/10 Excellent
Roberta W.
25 Aug 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Hemingway Hideaway was a gem. Located just a short walk from everything. We especially enjoyed watching the cruise ships come in as well as the sunset behind Opal Key resort. Be prepared to only bring one vehicle because only one parking space is allowed for this unit. That was a little bit of a challenge since we also wanted to have a golf cart for a family member with a recent knee replacement. We really enjoyed our stay there!
Roberta W.
Stayed 7 nights in Aug 2025
Verified
8/10 Good
jim h.
24 Jan 2024
Liked: Cleanliness, check-in, communication, location
happy place
great location/beautiful unit.only drawback was too many stairs
jim h.
Stayed 7 nights in Jan 2024
Verified
8/10 Good
Cathy F.
17 Mar 2025
Nice stay
We have stayed at many places in the annex. This was the first time at a three level. It was a lot for us. We are near 70 and my wife has foot issues so was quite a climb. But, the place was lovely.
Cathy F.
Stayed 12 nights in Feb 2025