Entire home

Hemingway Hideaway in the Truman Annex

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 spacious living room with a ceiling fan, large windows with blinds, a colorful rug, and a painting on the wall.
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 playground with a red slide and water play area, surrounded by palm trees and benches.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Duval Street

Popular amenities

  • Balcony
  • Private pool
  • Air-conditioning
  • Refrigerator
  • Washing machine
  • Internet

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

Rooms & beds

2 bedrooms (sleeps 6)

Guest Bedroom

1 Queen Bed

Living Area

1 Double Futon

Master Bedroom

1 King Bed

2 bathrooms, 1 half bathroom

Guest Bathroom

Bathtub or shower · Toilet

Master Bathroom

Toilet · Shower only

Powder Room

Toilet

Spaces

Kitchen
Balcony
Outdoor play area
Dining area

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

View from Front Porch
Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
Truman Annex
  • Pool
  • Kitchen
  • Washing machine
  • Dryer
10.0 out of 10, Exceptional, (193 reviews)
Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday

About the area

Key West

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.
View more Holiday homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Key West Naval Station - 1 min walk - 0.2 km
  • Harry S. Truman Little White House - 2 min walk - 0.2 km
  • Duval Street - 4 min walk - 0.4 km
  • Mallory Square - 6 min walk - 0.6 km
  • Ernest Hemingway Home and Museum - 11 min walk - 0.9 km

Getting around

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

Restaurants

  • ‪Margaritaville - ‬7 min walk
  • ‪Key Lime Pie Factory - ‬5 min walk
  • ‪Wendy's - ‬5 min walk
  • ‪The Bull & Whistle Bar - ‬5 min walk
  • ‪Fat Tuesday - ‬5 min walk

Frequently asked questions

Does Hemingway Hideaway in the Truman Annex have a pool?

Yes, this property has a pool.

How much does it cost to stay at Hemingway Hideaway in the Truman Annex?

As of 28 Oct, 2026, prices found for a 1-night stay for 2 adults at Hemingway Hideaway in the Truman Annex on 31 Aug, 2027 start from S$23,024, 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 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. Mallory Square and Florida Keys Beaches are also within 10 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
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

9.8/10

Check-in

9.6/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

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

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

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

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

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

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

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

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

Key West

Great Location
Stayed 7 nights in Apr 2024
Verified review

10/10 Excellent

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

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

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

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

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

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

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

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

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

8/10 Good

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

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

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

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

10/10 Excellent

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
Response from VrboOwner on 6 Jan, 2021
Thank you so much for the kind review of Hemingway Hideaway. We are pleased to hear you enjoyed your stay and will be back to join us again sometime.
Verified review

10/10 Excellent

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
Response from VrboOwner on 29 Nov, 2023
Dear Mr. John, Thank you for taking the time to review our property. We are pleased you enjoyed the unit and overall condition. We strive hard to ensure units are in top condition and guest find them clean and comfortable. If you wouldn’t mind since we did not hear from you during your stay regarding any bugs or light switch issues, could you please message their location so we can have that looked into? Or if you prefer you may also contact our office and we can discuss. Thank you again for joining us and Happy Holidays! - Conch Collection Management Team
Verified review

10/10 Excellent

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

Exactly what we had hoped for!

We loved our stay at this rental! It was so comfortable, well decorated, and just felt good. The beds were comfortable. The temperature control was great, even though it's three stories. Great and comfortable front porch! We love Key West and this served our needs very well. Truman Annex is beautiful and special and quiet. Couldn't be better! Thanks!
Stayed 7 nights in Jan 2023
Tell us how we can improve our siteShare feedback