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A PLEASANT STAY at The Truman Annex in Key West

Photo gallery for A PLEASANT STAY at The Truman Annex in Key West

Pool
Living area
Fridge, microwave, oven, stovetop
1 bedroom, iron/ironing board, free WiFi, bed sheets
Exterior

Reviews

9.2 out of 10
Wonderful

Entire condo

1 bedroom1 bathroomSleeps 2

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Kitchen
  • Pool
  • Outdoor Space

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

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, have central air conditioning, off street parking, and pool access. Just inside the Truman Annex's main gate on Southard Street this well-appointed, one-bedroom, second floor features tropical views and breezes. 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.

Property manager

Compass Realty Vacation Rentals & Property Management

Languages

English

Add dates for prices

Property amenities

Pool/Spa

  • Communal 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

  • Patio

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

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

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Pool

SUN, SEA, AND SKY at The Truman Annex in Key West

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  • Kitchen
  • Washer
  • Dryer
9.8 out of 10, Exceptional, 62 reviews
SUN, SEA, AND SKY at The Truman Annex in Key West

Policies

Check-in

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

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets not allowed

Children and extra beds

Children are welcome

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 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

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

About the neighborhood

Map
Key West, FL

What's nearby

  • Ernest Hemingway Home and Museum - 6 min walk - 0.5 km
  • Duval Street - 6 min walk - 0.5 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Mallory Square - 11 min walk - 1.0 km
  • Southernmost Point - 14 min walk - 1.2 km

Getting around

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

Restaurants

  • ‪Margaritaville - ‬7 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Green Parrot Bar - ‬6 min walk
  • ‪Bourbon Street Pub - ‬8 min walk
  • ‪Mangoes Restaurant & Island Cuisine - ‬7 min walk

Frequently asked questions

Is A PLEASANT STAY at The Truman Annex in Key West pet-friendly?

No, pets are not allowed at this property.

What time is check-in at A PLEASANT STAY at The Truman Annex in Key West?

Check-in begins at 4:00 PM.

Where is A PLEASANT STAY at The Truman Annex in Key West located?

Located in Old Town Key West, this condo building is within a 10-minute walk of We Cycle Key West, Duval Street, and Ernest Hemingway Home and Museum. Mallory Square and Fort Zachary Taylor Historic State Park are also within 15 minutes.

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A PLEASANT STAY at The Truman Annex in Key West Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 41 out of 65 reviews
Rating 8 - Good. 17 out of 65 reviews
Rating 6 - Okay. 6 out of 65 reviews
Rating 4 - Poor. 1 out of 65 reviews
Rating 2 - Terrible. 0 out of 65 reviews

9.2/10

Cleanliness

Reviews

This review comes from a trusted partner site and has not been verified.

10/10

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.

10/10

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

10/10

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

10/10

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
This review comes from a trusted partner site and has not been verified.

10/10

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

10/10

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
This review comes from a trusted partner site and has not been verified.

10/10

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!!!

8/10

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

10/10

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

10/10

Small but nice. No diswasher but lots of supplies in the unit.
Stayed 7 nights in Jan 2023
This review comes from a trusted partner site and has not been verified.

10/10

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.

8/10

Unit needs updating
Stayed 7 nights in Feb 2023

10/10

Had trouble with password taking affect.
Stayed 7 nights in Mar 2024

8/10

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
This review comes from a trusted partner site and has not been verified.

6/10

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.
This review comes from a trusted partner site and has not been verified.

4/10

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.
This review comes from a trusted partner site and has not been verified.

10/10

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.

8/10

Stayed 7 nights in Mar 2025
This review comes from a trusted partner site and has not been verified.

10/10

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: Perfect location and great accommodation
Stayed 8 nights in Nov 2024
This review comes from a trusted partner site and has not been verified.

10/10

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: First time staying at this location and in this rental. The proximity to everything was very ideal, nice walks to Southernmost and to the Harbor Walk. The Green Parrot is very close by, and became our nightcap for the evening. Rental was clean and was just enough for us. The neighborhood is quaint and quiet. The pool area was very nice as well. We will be looking at this rental on our future KW stays. Thank you!
Stayed 7 nights in Nov 2024
This review comes from a trusted partner site and has not been verified.

10/10

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.
This review comes from a trusted partner site and has not been verified.

10/10

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.
This review comes from a trusted partner site and has not been verified.

10/10

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.

10/10

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
This review comes from a trusted partner site and has not been verified.

8/10

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: The swimming pool closed at 6 p.m.This may be a deal breaker as we enjoy taking a swim at the end of the day