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Hemingway Hideaway in the Truman Annex

Vacation home near Duval Street in Key West

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Photo gallery for Hemingway Hideaway in the Truman Annex

A brick building with a number 21 sign, a staircase leading to a porch with blue chairs, and a view into the interior with a sofa and lamp.
A building with a brick facade, surrounded by lush greenery and trees.
A building with a brick facade, numbered 21, surrounded by lush greenery and a green gate.
A spacious living room with a ceiling fan, large windows with blinds, a colorful rug, and a painting on the wall.
A playground with a red slide and water play area, surrounded by palm trees and benches.

Reviews

9.8 out of 10
Exceptional

Entire home

2 bedrooms3 bathroomsSleeps 61527 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Key West, FL
  • Place, Harry S. Truman Little White House
    ‪2 min walk‬
  • Place, Duval Street
    ‪4 min walk‬
  • Place, Mallory Square
    ‪6 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪12 min drive‬

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About the neighborhood

Key West

Heart of Key West.Within a 10-minute walk of this Old Town Key West vacation home, you'll find Duval Street and Florida Keys Beaches. Also, Mallory Square is within half a mile (1 km) and Southernmost Point is within 2 miles (3 km).
View more Vacation Homes in Key WestOpens in a new window

What's nearby

  • Key West Naval Station - 1 min walk - 0.1 miles
  • Harry S. Truman Little White House - 2 min walk - 0.1 miles
  • Duval Street - 4 min walk - 0.3 miles
  • Mallory Square - 6 min walk - 0.4 miles
  • Ernest Hemingway Home and Museum - 11 min walk - 0.6 miles

Getting around

  • Key West Intl. Airport (EYW) - 14 min drive

Restaurants

  • ‪Margaritaville - ‬7 min walk
  • ‪The Bull & Whistle Bar - ‬5 min walk
  • ‪Key Lime Pie Factory - ‬5 min walk
  • ‪Fogarty's and Flying Monkey's - ‬5 min walk
  • ‪Wendy's - ‬5 min walk

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!

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Property amenities

Pool/Spa

  • Communal pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Car not required
  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • 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 elevator
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • 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
  • Snorkeling 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

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

  • No pets 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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, 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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Property is also known as

Hemingway Hideaway Truman Annex House Key West
Hemingway Hideaway Truman Annex House
Hemingway Hideaway Truman Annex Key West
Hemingway Hideaway Truman Annex
Hemingway Hideaway Truman Annex House Key West
Hemingway Hideaway Truman Annex House
Private vacation home Hemingway Hideaway in Truman Annex
Hemingway Hideaway Truman Annex Key West
Hemingway Hideaway Truman Annex
Hemingway Hideaway in Truman Annex Key West
Hemingway Hideaway in Truman Annex Private vacation home
Private vacation home Hemingway Hideaway in Truman Annex
Hemingway Hideaway in Truman Annex Key West

Frequently asked questions

How close is Hemingway Hideaway in the Truman Annex to the airport?

This vacation home is 4.1 mi (14-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Hemingway Hideaway in the Truman Annex have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Hemingway Hideaway in the Truman Annex to the beach?

This vacation home is a short 10-minute walk from Florida Keys Beaches and 1.2 mi (9-min drive) from South Beach. Don't forget your sunscreen!

Does Hemingway Hideaway in the Truman Annex offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Hemingway Hideaway in the Truman Annex?

No, there is no casino at this vacation home.

What time is check-in at Hemingway Hideaway in the Truman Annex?

Check-in begins at 4:00 PM.

Is there free parking at Hemingway Hideaway in the Truman Annex?

Free parking is not available at this vacation home.

Does Hemingway Hideaway in the Truman Annex have a pool?

Yes, there's a private pool.

Does Hemingway Hideaway in the Truman Annex have a spa?

There are no spa services available at this vacation home.

How close is Hemingway Hideaway in the Truman Annex to downtown Key West?

This vacation home is 0.3 mi away from Key West.

Hemingway Hideaway in the Truman Annex Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 61 out of 68 reviews
Rating 8 - Good. 5 out of 68 reviews
Rating 6 - Okay. 2 out of 68 reviews
Rating 4 - Poor. 0 out of 68 reviews
Rating 2 - Terrible. 0 out of 68 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Carolyn S.

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.
Stayed 7 nights in Nov 2025
Verified review

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was ideal for us. Clean, super comfy, great location.
Stayed 7 nights in Nov 2025
Verified review

10/10 Excellent

Michael S.

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

Great Stay

Great place with close to everything.
Stayed 7 nights in Dec 2023
Verified review

10/10 Excellent

Ryck S.

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

Great Week @ Hemmingway Hideaway!

Loved everything about this property!
Stayed 7 nights in Apr 2025
Verified review

10/10 Excellent

roberta i.

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.
Stayed 7 nights in Feb 2024
Verified review

10/10 Excellent

Katie H.

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!
Stayed 7 nights in Apr 2023
Verified review

10/10 Excellent

Teresa B.

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

Spring getaway

Great location, we walked or rode our bikes everywhere.
Stayed 7 nights in Feb 2024
Verified review

10/10 Excellent

Donald G.

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

January 2025 stay

A very nice property in a great location!
Stayed 7 nights in Jan 2025
Verified review

10/10 Excellent

Mary E.

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!
Stayed 7 nights in May 2024
Verified review

10/10 Excellent

Mitzi C.

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

Key West

Great Location
Stayed 7 nights in Apr 2024
Verified review

10/10 Excellent

Debbie M.

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!
Stayed 7 nights in Dec 2024
Verified review

10/10 Excellent

Rachel S.

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.
Stayed 9 nights in Aug 2023
Verified review

10/10 Excellent

Stephen D.

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.
Stayed 7 nights in Apr 2024
Verified review

10/10 Excellent

Susie D.

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!
Stayed 9 nights in Oct 2023
Verified review

10/10 Excellent

Matt H.

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!
Stayed 7 nights in Jan 2025
Verified review

10/10 Excellent

Mary N.

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.
Stayed 7 nights in Feb 2025
Verified review

10/10 Excellent

Brice C.

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!
Stayed 7 nights in Dec 2023
Verified review

10/10 Excellent

Ellen V.

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.
Stayed 7 nights in Aug 2024
Verified review

10/10 Excellent

Roberta W.

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!
Stayed 7 nights in Aug 2025
Verified review

8/10 Good

jim h.

Liked: Cleanliness, check-in, communication, location

happy place

great location/beautiful unit.only drawback was too many stairs
Stayed 7 nights in Jan 2024
Verified review

10/10 Excellent

RON S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Over all the unit was great. We had a great time and everything is in wall distance to the unit. Pool was great.We offer a few suggestions to make this unit excellent. Consider providing a tee pot for the non coffee drinkers. Your wine glasses were great, however there were no cocktail shakers for those that like to make cocktail. Also, consider a retractable close line in the bathroom so you have a place to dry clothes.As indicated we were pleased with our stay.R&R
Stayed 28 nights in Jan 2026
Verified review

10/10 Excellent

Paul L.

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!
Stayed 10 nights in Oct 2024
Verified review

10/10 Excellent

Tonja M.

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.
Stayed 7 nights in Aug 2023
Verified review

10/10 Excellent

Maxim M.

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

Best trip ever

Location location location. Very nice house in a quite neighborhood. Very close to everything. The house itself offers all you might need. We had no problems at all. Definitely coming back !!!
Stayed 7 nights in Dec 2020
Verified review

10/10 Excellent

John P.

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

Overall -Very nice vacation rental

Very nice unit. Many Light switches were not workiing with the lights , also found a couple of bugs (florida does have a lot)
Stayed 11 nights in Nov 2023

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