A License to Chill at the Truman Annex in Key West

Photo gallery for A License to Chill at the Truman Annex in Key West

A living room with two sofas, a coffee table, and a kitchen in the background.
A coastal hotel with a flagpole, a welcome sign, and a white picket fence.
A water park with a slide, a water fountain, and palm trees at sunset.
A backyard with a barbecue grill, a white fence, and a house number 12.
A modern kitchen with a large island, white countertops, and a blue accent wall.

Reviews

8.6 out of 10
Excellent

Highlights

  • Discover nearby landmarks
    Walk to Duval Street

Popular amenities

  • Balcony
  • Swimming pool
  • Air-conditioning
  • Refrigerator
  • Washing machine
  • High-speed internet

Explore the area

View 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)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

2 bathrooms, 1 half bathroom

Bathroom 1

Toilet

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Balcony

Add dates for prices

Similar properties

View from Front Porch
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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 on the waterfront, this holiday home is in Old Town Key West, a neighbourhood 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. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. With jet skiing, scuba diving and snorkelling nearby, you'll find plenty of adventures in the water.
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
  • ‪Green Parrot Bar - ‬7 min walk
  • ‪Key Lime Pie Factory - ‬5 min walk
  • ‪Wendy's - ‬5 min walk
  • ‪The Bull & Whistle Bar - ‬5 min walk

Frequently asked questions

Does A License to Chill at the Truman Annex in Key West have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at A License to Chill at the Truman Annex in Key West?

As of 30 Oct 2026, prices found for a 1-night stay for 2 adults at A License to Chill at the Truman Annex in Key West on 1 Dec 2026 start from AU$15,053, 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 A License to Chill at the Truman Annex in Key West pet-friendly?

No, pets are not allowed at this property.

How much is parking at A License to Chill at the Truman Annex in Key West?

On-site parking is available at the property.

What time is check-in at A License to Chill at the Truman Annex in Key West?

Check-in begins at 4:00 PM.

What time is check-out at A License to Chill at the Truman Annex in Key West?

Checkout is at 10:00 AM.

Where is A License to Chill at the Truman Annex in Key West 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

8.6

Excellent

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 23 out of 38 reviews
Rating 8 - Good. 6 out of 38 reviews
Rating 6 - Okay. 6 out of 38 reviews
Rating 4 - Poor. 2 out of 38 reviews
Rating 2 - Terrible. 1 out of 38 reviews

8.8/10

Cleanliness

8.8/10

Check-in

9.2/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Amazing location, ease of access to old town.

Would recommend for sure. Location was great, everything within walking distance and pool was amazing as well!
Stayed 7 nights in May 2022
Response from VrboOwner on 15 Sept 2023
Thank You!
Verified review

10/10 Excellent

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

Key West Bliss

Walk to Duval Street; bike to the beach; quiet location..... perfect!
Stayed 8 nights in Dec 2023
Response from VrboOwner on 9 Jan 2024
Thanks for staying with Compass Realty!
Verified review

10/10 Excellent

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

Clean property, with excellent location.

Everything went very well no problems with the property.
Stayed 7 nights in Apr 2023
Response from VrboOwner on 15 Sept 2023
Daryl thank you for this wonderful review, we are so glad you enjoyed your stay with us here at Compass Realty and hope to host you again next time you visit the island!
Verified review

10/10 Excellent

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

Calm relaxed location

The central location of the property made each day easy to get to the locations we wanted, usually with a very short walk. Yet as close to the action it was, the design and security of the property provided a very calm and tranquil experience.
Stayed 7 nights in May 2022
Response from VrboOwner on 15 Sept 2023
Thank You!
From a partner site

10/10 Excellent

Very nice vacation

Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: Great location. Within walking distance of many attractions, yet still in a quiet area.
Response from VrboOwner on 15 Sept 2023
Thanks for staying with Compass Realty!
Verified review

8/10 Good

Liked: Cleanliness, communication, location, listing accuracy

Location location location

Perfect spot if you are interested in parking the car and walking everywhere. The condo’s furnishings are a little “tired” but not enough to make it a problem. Note. TV stations very limited and all non-HD stuff. Washer was’t working while we were here but we were reimbursed for trip to laundry.
Stayed 7 nights in Dec 2019
From a partner site

6/10 Okay

Too tired

Rating Details: The property manager was very helpful. The vacation rental was clean. I was very happy with the location. I was very dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: We enjoyed our stay in spite of the very tired accommodation! Great location. Your services were great! We can’t believe this owner keeps the condo as it is. Holes in furniture, front door that barely closes, delaminated bath tubs, rotten wood, peeling paint, towel racks that fall off the wall, terrible plumbing and the FILTHIEST area rug we have EVER seen and what is probably black mold on the HVAC vent in main bathroom. Kitchen ill equipped, not even a pot holder in the place.
From a partner site

6/10 Okay

Close enough, yet far enough

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Property is in a beautiful area and enjoyed our walks to town and park. Good restaurants and attractions in walking distance. The condo itself was clean and had enough items in kitchen for us to use. It could definitely use an update as far as furniture goes. Bathrooms could use a refresh. Master bedroom bed as comfy. Upstairs bed also needs a refresh. I would stay here again.
From a partner site

6/10 Okay

Foundry Truman Annex

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was very dissatisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Overall the property was acceptable and in an excellent location. It does need some minor maintenance and refreshing. The kitchen could use additional utensils
From a partner site

10/10 Excellent

Key West 2024

Rating Details: The property manager was more than 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: This was another excellent week in the Truman Annex area of Key West. Quiet and relaxing area to stay.
From a partner site

6/10 Okay

Review- L to Chill.

Rating Details: The property manager was somewhat unhelpful. The vacation rental was somewhat dirty. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: All was fantastic, EXCEPT overall cleanliness.
Verified review

10/10 Excellent

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

Wonderful Week at Truman Annex

Perfect location, within walking distance of everything we needed. The unit was clean, well-appointed and very comfortable for two couples.
Stayed 7 nights in Jun 2022
From a partner site

10/10 Excellent

Amazing 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: We loved staying here. Everything was very clean and the location of the condo is perfect! We always stay in Truman Annex every time we come to Key West!
Verified review

10/10 Excellent

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

Great location

Very convenient, comfortable and clean.
Stayed 7 nights in May 2022
From a partner site

10/10 Excellent

All good

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 love Truman Annex, and every unit we have rented in the Foundry has been wonderful. This unit was convenient, well appointed, and clean. We enjoyed the pool and it was very nice to have a gas grill and well equipped kitchen. The people at Compass were very professional and helpful.
From a partner site

4/10 Poor

Great Location, Description Misleading!

Rating Details: The property manager was adequately helpful. The vacation rental was very dirty. I was very happy with the location. I was very dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: The location of was great! The Truman Annex is a special place. The unit itself was not clean-- and not well equipped. Zero beach towels, only two rusty beach chairs. The description is wrong. Replacing a refrigerator is not a fully renovated kitchen. The dishes were mismatched, it looked like a frat house and they were dirty. I sent a full email with all the issues to include photos. broken blinds, cracked tile, worm out sheets-- the list goes on. This unit needs a major overhaul. We will never rent this particular unit again.
From a partner site

10/10 Excellent

FF 2021

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: It was my 16th FF, and I've stayed in the Foundry townhouses for 5 of them with my wife and friends. This was my 2nd stay in "A License to Chill". We've always found the Foundry townhouses very comfortable, quiet, and convenient to the places we go to, and being able to park at our front door is very convenient also.
From a partner site

6/10 Okay

Needs update

Rating Details: The property manager was very helpful. The vacation rental was clean. 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: While we realize that rental property is difficult to maintain, the townhouse is in serious need of a bathroom and furniture update. The bath fixtures are old and not in the best condition. The living room furniture is completely worn out also. The tv connection would only allow us to watch one channel in the living area. This was our tenth stay in Truman Annex and we were disappointed in this unit. Someone needs to give it a walk through to address multiple maintenance needs.
From a partner site

10/10 Excellent

License to Chill

Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: Love the location.
From a partner site

10/10 Excellent

Wonderful place to stay in an exceptional part of Old Town Key We

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 condo is very nice and clean. The rental office is friendly and helpful. The location is close to everything, yet nicely secluded and private.
From a partner site

4/10 Poor

Ok

Rating Details: The property manager was more than helpful. The vacation rental was very dirty. 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: When we arrived, there were two spider webs (TV area and ceiling fan), dog treats on the floor, stains on the area rug, couch, and loveseat and a good amount of mold around both tubs. Although they sent out a cleaning service, a pest control person and a wet vac person to clean the rug/furniture, the bathrooms remain an issue and overall it felt like it needed a little TLC.
Stayed 21 nights in Mar 2022
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy

Great Location

We had a grewat
Stayed 7 nights in Feb 2022
Verified review

8/10 Good

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

Great location!

We loved the Truman Annex property - walking distance to all of the great restaurants, bars, and sights. This property was perfect for our group of 3, though it could use a few updates. Overall was a lovely stay!
Stayed 7 nights in Jan 2022
Verified review

8/10 Good

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

Vacationers in Key West

The staff at Compass Realty were very professional and answered all questions prior to arrival. The property was clean, however, furniture could stand to be updated. Location was excellent.
Stayed 7 nights in Jan 2022
Verified review

10/10 Excellent

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

Family vacation

From beginning to the end was a pleasant experience. Location is great and the rental company Michelle was my contact person was awesome!!!
Stayed 7 nights in Jan 2022
Response from VrboOwner on 15 Sept 2023
Thank you so much for the great feedback! -Compass Realty
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