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A Pleasant Stay at The Truman Annex in Key West

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Photo gallery for A Pleasant Stay at The Truman Annex in Key West

A water park with a slide, a water fountain, and palm trees at sunset.
A two-story house with a porch, surrounded by lush greenery and a white picket fence.
A porch with a white door marked "102 11-", a doormat, and a white railing.
A hallway with a mirror, a black console table with a lamp, and a staircase.
A living room with a red sofa, a wooden coffee table, a patterned rug, and a ceiling fan.

Reviews

9.2 out of 10
Wonderful

Entire condo

1 bedroom1 bathroomSleeps 21 sq ft

Popular amenities

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

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪8 min walk‬
  • Place, Fort Zachary Taylor Historic State Park
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 min drive‬

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About the neighborhood

Key West

Located in Old Town Key West, this condo is within a 10-minute walk of popular sights such as Duval Street and Ernest Hemingway Home and Museum. The condo includes a private pool, a kitchen, and a balcony.
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What's nearby

  • Florida Keys National Marine Sanctuary - 5 min walk - 0.3 miles
  • Duval Street - 6 min walk - 0.4 miles
  • Ernest Hemingway Home and Museum - 8 min walk - 0.4 miles
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.4 miles
  • Mallory Square - 12 min walk - 0.7 miles

Getting around

  • Key West Intl. Airport (EYW) - 19 min drive

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Moondog Cafe & Bakery - ‬8 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Rams Head Southernmost - ‬7 min walk

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

A Pleasant Stay at The Truman Annex in Key West

Just inside the Truman Annex's main gate on Southard Street, this well-appointed, very popular one-bedroom, second floor gem features tropical views and breezes and yet it's only two blocks from the heart of Old Town Key West, with an easy walk to restaurants, shops and many other Key West attractions. A Pleasant Stay boasts a large rear deck with a 50% overhang to protect you from the elements while enjoying the shade of lush palm trees and other vegetation. You'll stroll through floral-lined lanes to Shipyard's around-the-corner private pool. Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fort Zachary Taylor State Park. The property is outfitted with washer/dryer, pots/pans, towels, linens, central air conditioning, off street parking, and pool access.
Please note: This property has a 27 night minimum stay.
The condo is air-conditioned and features a kitchen and a balcony, and there's space to spread out with a separate bedroom. Guests can expect to find free WiFi. Other standard amenities include a private pool, a washer/dryer, and a coffee maker.

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  • Kitchen
  • Washer
  • Dryer
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Property amenities

Pool/Spa

  • Communal pool
  • Heated pool
  • Private pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • Bedroom
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Outdoor areas

  • Balcony

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near the marina
  • Near the sea

Things to do

  • Heated pool
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Gated community
  • Unit size: 1 square foot

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a fire extinguisher and a smoke detector.

Property is also known as

Pleasant Stay Truman Annex House Key West
Pleasant Stay Truman Annex House
Pleasant Stay Truman Annex Key West
Pleasant Stay Truman Annex
A Pleasant Stay in the Truman Annex
A Pleasant Stay @ the Truman Annex Key West
A Pleasant Stay @ the Truman Annex Private vacation home
20% off Summer Special A Pleasant Stay @ the Truman Annex
2698-193239

Frequently asked questions

What's there to see close to this condo?

This condo is situated in Old Town Key West within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum. You'll also find Florida Keys Beaches and Mallory Square less than a mile away.

Is there parking available at A Pleasant Stay at The Truman Annex in Key West?

No, there isn't parking at this condo.

Is this condo adjacent to a casino?

No, this condo is not connected to a casino.

Is there an indoor pool at this condo?

No, there is no indoor pool at this condo; however, the accommodation features a private pool.

What do couples enjoy most about A Pleasant Stay at The Truman Annex in Key West?

Couples staying at this condo will appreciate amenities like a private pool and a kitchen as well as a heated pool.

Are there hot tubs at A Pleasant Stay at The Truman Annex in Key West?

No, but guests can enjoy a heated pool at this condo.

Does this condo provide breakfast?

No, this condo doesn't offer breakfast.

Does this condo allow pets to stay for free?

No, pets aren't allowed at this condo.

Are there connecting rooms at A Pleasant Stay at The Truman Annex in Key West?

No, this condo doesn't feature connecting guestrooms.

What is the closest airport to this condo?

The closest major airport to this condo is Key West Intl. Airport (EYW), which is 4.1 mi away (19 minutes by car).

Are there rooms with balconies at A Pleasant Stay at The Truman Annex in Key West?

Yes, every condo at A Pleasant Stay at The Truman Annex in Key West comes with a balcony.

A Pleasant Stay at The Truman Annex in Key West Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 45 out of 69 reviews
Rating 8 - Good. 17 out of 69 reviews
Rating 6 - Okay. 6 out of 69 reviews
Rating 4 - Poor. 1 out of 69 reviews
Rating 2 - Terrible. 0 out of 69 reviews

9.2/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Anthony R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful stay!
Stayed 7 nights in Dec 2025
Verified review

10/10 Excellent

Agnes B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was very clean , quiet and close to everything.
Stayed 14 nights in Dec 2025
Verified review

10/10 Excellent

David W.

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

Key West is Great

The condo is as described with a great location.
Stayed 7 nights in Feb 2024
Verified review

10/10 Excellent

Elizabeth C.

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

A VERY pleasant stay!

Everything was within walking distance, and being so near the Truman Water park for sunsets was fantastic! We enjoyed the small neighborhood feel of the Truman annex and are planning to return next year!
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

Brent H.

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

Great little place

This condo was a great little place to stay in Key West. It was within walking distance of just about everything. We would definitely stay there again.
Stayed 7 nights in May 2023
From a partner site

10/10 Excellent

Keith M.

A Pleasant 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: This is a wonderful rental to stay in. This is our second time there and my wife and I love it. So nice and convenient to everything that Key West has to offer !!!
Verified review

10/10 Excellent

Susan B.

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

Shipyard 1 BR

perfect size with a great porch.
Stayed 7 nights in Apr 2025
Verified review

10/10 Excellent

Belinda P.

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

Pleasant Stay

Overall very satisfied with our accommodations. We highly recommend this Condo for it’s location and community setting. We rented bicycles for the week and it was easy to get out and explore everything Key West has to offer.
Stayed 7 nights in May 2023
From a partner site

10/10 Excellent

tony p.

Great Spot

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: Great location to DUVAL St and Taylor beach State Park!
Stayed 8 nights in Jun 2024
From a partner site

10/10 Excellent

Stephen H.

A Pleasant 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 our stay. Absolutely love Key West!!!
From a partner site

10/10 Excellent

Dorothy K.

A Pleasant Stay

Rating Details: The property manager was very 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: Great location in walking distance to everything. Compass Realty people are friendly, helpful and will fix any issue that may come up.
Verified review

10/10 Excellent

Courtney H.

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

2nd wedding anniversary

Wr enjoyed our stay very convenient to duval street. Loved the condo and will definitely want this location again in 2 yrs when we come back as we come to key west every other year since we got married in key west in 2021.
Stayed 8 nights in Jun 2023
From a partner site

10/10 Excellent

Mathew G.

Truly was a pleasant stay

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: It was my wife and I first time together in Key West. We got married in key west and then honeymooned there as well. Location was perfect. Short walk to anywhere.
Verified review

10/10 Excellent

Dan C.

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

Delightful week

We had a wonderful week staying in unit 102-11. Very clean, nice deck, comfortable bed and couch. Kitchen had everything we needed. Made good use of the washer and dryer. All needed supplies were in the unit. Excellent location. Close to everything….including the Green Parrot!
Stayed 7 nights in Jan 2025
Verified review

10/10 Excellent

Ronald N.

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

Very enjoyable

Small but nice. No diswasher but lots of supplies in the unit.
Stayed 7 nights in Jan 2023
From a partner site

10/10 Excellent

Paul B.

Yearly visit

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: Another wonderful time. The place was again just great..clean and everything I need. Perfect location close to everything. See you next year.
Verified review

8/10 Good

jim h.

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

Buffet show

Unit needs updating
Stayed 7 nights in Feb 2023
From a partner site

10/10 Excellent

Julie J.

Another fantastic 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: This unit is clean, extremely well located and had the most comfortable bed. Great for relaxing after a day enjoying everything Key West has to offer. It has a private deck, which is a great place to read and watch the weather. They installed new windows over the last year and they are wonderful. It's also the only property in key west I've stayed that has a bathtub/shower, which makes me very happy.
Verified review

8/10 Good

Clay W.

Liked: Cleanliness, location

Incredible Location!

The property is in an incredible location for visiting Key West. We would stay at the property again. The unit itself was dated and a bit tired. It is in need of updating and refreshing. I would not stay in the same unit again at the price. The unit also had bugs and spiders; it is south Florida so it did not freak us out but it would some people.
Stayed 10 nights in Dec 2024
Verified review

8/10 Good

Jeff B.

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

Location Location Location

We love staying at Truman Annex - it’s close to everything, including the Green Parrot and a short bike ride to Fort Zach, Duval, and the pier. While we also enjoy the pool, this was our first time visiting in May and it could be quite crowded and loud. The condo was just what we needed - plenty of dishware, washer & dryer, and patio seating. Our only wish is a small one in that we wished there was more storage space for our clothes but we totally made do.
Stayed 7 nights in May 2022
Verified review

10/10 Excellent

Ed H.

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

WiFi

Had trouble with password taking affect.
Stayed 7 nights in Mar 2024
From a partner site

6/10 Okay

Kathleen F.

Uncomfortable Stay

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: The location was great. The bed was awful,very uncomfortable. The pictures show a table and chairs on the deck , but there was only a table,no chairs.We definitely have stayed in much more updated and comfortable units in the Annex.
From a partner site

10/10 Excellent

Paige O.

Spring Break 2023 A Pleasant Stay

Rating Details: The property manager was very helpful. The vacation rental was 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: This is the 3rd time I have dealt with Compass Realty. They are quick to respond and friendly to deal with. I have stayed at 3 properties in Shipyard Condominiums.This property was the smallest, but the location of the door on the street was a nice advantage this time. This particular property was slightly dated, but very much met our needs. There were bugs in the bathroom which would be my biggest complaint. Closet door was broken, only 5 hangers for a week stay, more would have been nice. I will continue to rent from this company as long as prices remain somewhat steady.
From a partner site

4/10 Poor

David G.

Needs updating

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: Unit needs serious updating. The bathroom fan worked the first two days then died. The garbage disposal did not work. The bathroom faucets were both loose. Everything seems to be original. Light bulbs were missing or burnt out in lamps. Stairway carpeting needs cleaning.
From a partner site

10/10 Excellent

A guest from Stanford, KY

Wonderful two weeks

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 have rented a condo in the Shipyard community in Truman Annex from Compass Realty at least 20 times. We love the location because it is within walking distance of all the places we like to go. Compass Realty makes renting very easy. We have stayed at nearly every one bedroom condo that Compass manages over the last many years. I like some a little better than others and Pleasant Stay was fine. Only one complaint. The bedroom closet was so full of bedding, blankets, pillows, etc. and with no dresser for clothes, it was difficult to find a place to put suitcases or to unpack. Also be aware that this condo does not have a dishwasher. That said, Key West is so great, a little inconvenience is ok.

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