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SOUTHARD COMFORT at The Truman Annex in Key West

Photo gallery for SOUTHARD COMFORT at The Truman Annex in Key West

Living area
Living area
Living area
Terrace/patio
Living area

Reviews

9.2 out of 10
Wonderful
2 bedrooms1 bathroomSleeps 463.2 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪5 min walk‬
  • Place, Fort Zachary Taylor Historic State Park
    ‪8 min walk‬
  • Place, Mallory Square
    ‪9 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪14 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony

About this property

SOUTHARD COMFORT at The Truman Annex in Key West

LOCATION, LOCATION, LOCATION! Southard Comfort is on Southard Street in the TRUMAN ANNEX, which is one of the most beautiful peaceful retreats and uniquely close to everything, Key West. We are only two blocks from the main Duval Street with it’s bustling shopping, bars, restaurants, & nationally renowned entertainment spots. Southard Comfort is one block from the infamous Green Parrot and is walking and biking distance to everything you will require for a comfortable stay. There is the Truman Waterfront Park for the children with beautiful sunset and water views just a hop away.
As one of our first guests to enjoy value and comfort in our refreshed, 2 bedroom 1 bath, 2nd floor condominium. You can enjoy televisions in every room, unlimited WIFI, USB charging stations, Keurig and drip coffee makers, washer and dryer, dual balconies and even a front porch. Southard Comfort comes equipped with a light and bright queen bedroom and twins (or King if combined) in the guest room. The condo has been freshly painted, updated and fully air-conditioned and all rooms have tropical ceiling fans. The balconies are situated to provide a wonderful open-air feel and cross breeze. The linens are new, including beach and pool towels. The full kitchen has a large refrigerator, stove with oven, microwave, blender, pots, pans and all the dishes necessary to enjoy a long stay.
Key West boasts an average daily temperature of 82 degrees keeping the ocean water temps at around 80. The Truman Annex SHIPYARD is a clean and safe hideaway, with parking for one car, near all the fun in Key West. Southard Comfort is directly on the parade route for Fantasy Fest and is ideal for couples, families, and seniors. 28 night stay minimum.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space

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  • Washing machine
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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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
On-site 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 that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the area

Key West

Located in Key West, this condo is in the city centre. Fort Zachary Taylor Historic State Park and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. USCGC Ingham Maritime Museum and Mel Fisher Maritime Museum are also worth visiting.
Map
Key West, FL

What's nearby

  • Duval Street - 5 min walk - 0.4 km
  • Florida Keys National Marine Sanctuary - 5 min walk - 0.4 km
  • Ernest Hemingway Home and Museum - 7 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Mallory Square - 9 min walk - 0.8 km

Getting around

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

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Margaritaville - ‬7 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪La Concha Bar - ‬8 min walk

Frequently asked questions

Is SOUTHARD COMFORT at The Truman Annex in Key West pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at SOUTHARD COMFORT at The Truman Annex in Key West?

As of 17 April 2026, prices found for a 1-night stay for 2 adults at SOUTHARD COMFORT at The Truman Annex in Key West on 30 April 2026 start from NZ$246, 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.

How much is parking at SOUTHARD COMFORT at The Truman Annex in Key West?

On-site parking is available at the property.

What time is check-in at SOUTHARD COMFORT at The Truman Annex in Key West?

Check-in begins at 4:00 PM.

What time is check-out at SOUTHARD COMFORT at The Truman Annex in Key West?

Checkout is at 10:00 AM.

Where is SOUTHARD COMFORT at The Truman Annex in Key West located?

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

Reviews

9.2

Wonderful

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. 21 out of 31 reviews
Rating 8 - Good. 7 out of 31 reviews
Rating 6 - Okay. 2 out of 31 reviews
Rating 4 - Poor. 1 out of 31 reviews
Rating 2 - Terrible. 0 out of 31 reviews

9.8/10

Cleanliness

8.8/10

Check-in

8.4/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

From a partner site

10/10 Excellent

A guest from South Bend, IN

Truman Annex is the Best

Rating Details: The property manager was very helpful. The vacation rental was spotless. 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: Fantastic location: Walk everywhere, beautiful, close to all the action, but quiet. Best in Key West. Loved the balconies. Rental clean and in good repair. Could use a large stainless steel bowl for salads and mixing.Management is super responsive.
Verified

10/10 Excellent

Tami C.

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

Spring Break Getaway

We stayed here in late April and it was perfect. The pool is directly behind the property and we were only a few blocks away from Duval Street, a seafood market, and a grocery store. Place is quiet and clean.
Stayed 7 nights in Apr 2025
Verified

10/10 Excellent

Gillian C.

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

Fabulous

Great location and fabulous property. Hope to stay again soon. We visit every year!
Stayed 7 nights in Oct 2023
Verified

6/10 Okay

Anna M.

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

Truman Anex

Wonderful place Clean and very convenient to all activities. I would highly recommend this place for families with small children as well as teenagers.
Stayed 7 nights in Mar 2024
From a partner site

8/10 Good

Eric P.

Thanksgiving Key west style....

Rating Details: The property manager was more than helpful. The vacation rental was very clean. I was very happy with the location. I was somewhat dissatisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Check in and check out was simple. House was in good shape furniture was a little uncomfortable and beds were small but overall great time.
Verified

10/10 Excellent

Phyllis S.

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

Truman Annex Condos - 5 star location

his property is managed by Compass Realty. Do not expect to communicate with an owner. Nonetheless Compass communicated well before, during and after our stay. They had everything prepared for our arrival and few essentials on hand to help us get started.We love the location of this condo! There’s a waterfront park at the end of the street, it’s minutes away from the beach at the state park and easy walking distance to the best Key West restaurants. We do not rent a car while in Key West because we don’t need one while staying in The Truman Annex. We love this area and hope to return
Stayed 14 nights in Jan 2025
Verified

10/10 Excellent

Kimberly B.

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

Southard retreat

We enjoyed our stay at the property. Compass reached out prior to our trip to provide check in instructions and answer any questions which I thought was helpful. The unit was very clean and had everything we needed. We arrived during an unusual cold spell and there were plenty of extra blankets which were needed our first nights! We had everything we needed. We loved the location. By the end of the week it was hot in the unit. That was our only challenge. Otherwise it was a perfect week!
Stayed 7 nights in Dec 2022
From a partner site

8/10 Good

theresa r.

Terrific location

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: I've stayed at several properties in the Truman Annex. This is a great location, well stocked with everything you need for cooking breakfast or heading to the beach. There was a plumbing issue at the beginning of our stay but the management company was very responsive and the issue was corrected within a couple of hours. One other item to note, we were instructed to keep the AC at 78-83 degrees. We were told that there was a concern that the AC would freeze up. We were able to compromise on this and get the AC to a comfortable temperature for sleeping. Overall, a wonderful location, great property and I would stay here again.
Stayed 7 nights in May 2021
From a partner site

10/10 Excellent

Steve K.

Our July '24 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've been staying at this unit the last couple of years including earlier this year in May. We like the unit. It is clean and has all the necessities. My wife, Marie, especially likes the location on Southard Street where she can watch the traffic go by.
From a partner site

10/10 Excellent

Steve K.

Our third stay at Southard Comfort

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 been visiting Key West and Shipyard for about 10 years now, the last three staying at Southard Comfort. The unit is kept very clean and has all the necessities. My wife especially likes the location on Southard Street where she can watch the traffic go by from the balcony. And, it is a short two block walk to Duval Street.
From a partner site

10/10 Excellent

A guest from South Bend, IN

202-9 SY

Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: Perfect everything: location, property management, community swimming pool, 2 balconies,full kitchen!Property was clean and adequate, but decor needs a tropic modern make-over to brighten it up- walls are grey, rugs are grey and tired, chair cushions are grey and don't fit, balconies and furniture could use a power wash. A interior decorator could make this place amazing.
From a partner site

10/10 Excellent

Stephen Z.

Key West NYE 2024

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: Enjoyed our stay the unit was comfortable
From a partner site

8/10 Good

A guest from South Bend, IN

202-9 Southard, Truman Annex

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: New patio pillows add fresh color and charm. Large new white plastic mixing bowls were a useful addition for making salads, and new pots and pans appreciated for cooking. Loved also the new awning over back balcony- perfect balance of sun and shade. Perfect location within walking distance of many attractions and amenities (city and state parks, museums, farmer's market, downtown) Truman Annex is a semi-gated community that is beautifully landscaped and maintained- a jewel.Loved the balconies and fun view of pedestrian life.Office staff goes above and beyond to help. Apt was clean and kitchen well supplied.Living room furniture and rugs are a bit dreary and well worn, but this is a great place to stay and would recommend it.
From a partner site

8/10 Good

A guest from Huntington, AR

Thanksgiving in the Keys

Rating Details: The property manager was very helpful. 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: We’ve been to Key West a number of times. This was our first stay in a condo at the Shipyards. The property was very nice. Our only problem was one of the beds had been urinated in and smelled poorly. Once reported, the management team replaced the mattress. This made for one not so good night. Location was great. We were close to everything and walked most of the time. Unit was quiet and well maintained. We would stay at this location again but probably not in this unit. The second bedroom had twin beds which were not comfortable for an adult. Giving low ratings for bed issue under furniture and cleanliness. Everything else was perfect.
From a partner site

6/10 Okay

Lorraine S.

Great Location

Rating Details: The property manager was somewhat unhelpful. The vacation rental was very clean. 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: This rental was a great location. The unit was good. Check-in is a nightmare! Photos a bit deceiving, as not much space for 4 people. Furniture and beds were cheap quality and not comfortable. Having stayed in KW before, this time we wanted a place to enjoy and relax during “down time”. I had to resort to the porch for that while my group was in the living room. Bathroom was SMALL! Not enough cook wear in the kitchen. But the place was clean and good location. It was quite insulting to read a sign on thermostat to keep at 78°-80° when you’re in KW!
From a partner site

10/10 Excellent

Charles S.

Southard Comfort

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 was a nice condo and well located. Compass Realty was a breeze to deal with.
From a partner site

10/10 Excellent

Sunny A.

Great 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 had a amazing time in Key West and the condo we stayed in was great and in a great location. We were able to walk everywhere. Which made it great not having to look for a place to park a car. Everyone at the realty company was very nice and helpful. We will be staying here again.
From a partner site

8/10 Good

AMY K.

Had a great time

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We enjoyed the rental. It was nice that it was so close to duval and everything. The layout of everything was confusing and we parked in the wrong slot for awhile but once we got that figured out it was nice. Very comfortable and had everything we needed.
From a partner site

10/10 Excellent

Steve K.

Another Excellent 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've been visiting Key West for about nine years now, with the exception of the covid year, and have always stayed in Shipyard. We've booked thru Compass Realty several times and have always been very happy - highly recommended. As to this unit, very clean and nicely decorated, and important to us - plenty of towels. No complaints here about this unit. Highly recommended!
From a partner site

10/10 Excellent

Tom V.

Clean and well maintained

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 helpful for providing keys at the office that we can get early. We supposed to check in by 4pm, but we arrived at Key West by noon. 4 hours to kill. The housekeepers were polite and very accommodating. They let us to leave our luggage in the condo and we can come back after 4pm. Thank you for your top notch services and clear instructions.
From a partner site

10/10 Excellent

jerry z.

Love the ship yard !

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 time as always. We love 202-9 as my in laws used to own that unit so me and my family have been there so much we feel like it's home ! So happy we can rent it. It is a very nice and updated unit !
From a partner site

10/10 Excellent

Lisa T.

Everything is perfect in Paradise

Rating Details: 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: What wonderful little condo! Very clean and comfortable. Super close to everything!
From a partner site

10/10 Excellent

Cyndi J.

Southard Comfort is a Great Place to Stay in a Great Location!

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 unit has everything needed for a wonderfully relaxing vacation. We enjoyed the front and back balconies for coffee in the morning and drinks in the evening. The property description is spot on and the unit is clean. The location can't be beat! We could walk everywhere. The parking spot and bike racks are bonuses! The Compass Realty staff was friendly, helpful, and professional. Their check-in and check-out processes are smooth and easy. We can't wait for our next trip to Key West!
From a partner site

10/10 Excellent

A guest from South Bend, IN

Look no further than the Truman Annex with Compass Realty

Rating Details: The property manager was very helpful. The vacation rental was spotless. 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: We had a fantastic time and the Compass staff was outstanding- kind, flexible, helpful.Property was very clean and well maintained. Furnishings were a bit old (couch springs and stuffing were worn out), and the colors dreary ( gray walls, gray brown floor, gray blue furniture). But we loved the front balcony with its love seat and table.Key West, Compass and Truman Annex are the best. The Annex is gorgeous, and the best location in town: quiet, easy to walk everywhere, wouldn't stay anywhere else. Thank you again for a fantastic vacation, superb location, and exceptional staff.
From a partner site

10/10 Excellent

thomas h.

March in Old town Key West

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: I have stayed in Truman Annex several times over the last 15 years. The location is perfect, and the community pool is a great bonus! Compass Reality is always a pleasure to deal with and very well organized. The guards at the main entrance could be a little more pleasant but that is my only complaint. I hope to be back next winter and booking thru Compass Reality is definitely my 1st choice.

About the host

Hosted by Compass Realty Vacation Rentals & Property Management

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