SOUTHARD COMFORT

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.

Vacation Rental Reviews

• Truman Annex is the Best

  Stayed 42 days ending in February, 2026

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  Sam S from South Bend, IN recommends this vacation rental

  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.

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• Southard Comfort

  Stayed 41 days ending in April, 2025

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  Joy B from Beach Haven, NJ recommends this vacation rental

  Fabulous!!! Great location. Perfect condo for my husband and I

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• Lovely Location

  Stayed 42 days ending in March, 2025

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  Sam S from South Bend, IN recommends this vacation rental

  Everything was excellent except the decor is dreary.

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• Location is Key on Key Wedt

  Stayed 14 days ending in January, 2025

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  Phyllis S from Lexington, KY recommends this vacation rental

  Compass Realty manages this property and communication before, during and after our stay was excellent. The property is clean and pleasingly decorated. There is no better location to experience Key West than the Truman Annex. Our condominium was easy walking distance to the best restaurants, the state park beach and a waterfront park is located at the end of the street. I highly recommend the Truman Annex condominiums and Compass Realty for a memorable stay in Key West!

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• Very nice condo!

  Stayed 9 days ending in December, 2024

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  ROBERT S from CRANDON, WI recommends this vacation rental

  Very nice upper unit. Would definitely stay here again.

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• Our July '24 stay

  Stayed 8 days ending in July, 2024

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  Stephen K from Manchester, CT recommends this vacation rental

  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.

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• Our third stay at Southard Comfort

  Stayed 7 days ending in May, 2024

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  Stephen K from Manchester, CT recommends this vacation rental

  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.

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• 202-9 SY

  Stayed 42 days ending in March, 2024

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  Sam S from South Bend, IN recommends this vacation rental

  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.
  
  

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• Key West NYE 2024

  Stayed 7 days ending in January, 2024

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  Stephen Z from Melville, NY recommends this vacation rental

  Enjoyed our stay the unit was comfortable

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• 202-9 Southard, Truman Annex

  Stayed 35 days ending in March, 2023

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  Sam S from South Bend, IN recommends this vacation rental

  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.
  

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• Thanksgiving in the Keys

  Stayed 7 days ending in November, 2022

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  a guest from Huntington, AR recommends this vacation rental

  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.

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• Great Location

  Stayed 7 days ending in November, 2022

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  Lorraine S from Navarre, FL recommends this vacation rental

  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!

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• Southard Comfort

  Stayed 7 days ending in June, 2022

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  Charles S from Shoals, IN recommends this vacation rental

  This was a nice condo and well located. Compass Realty was a breeze to deal with.

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• Perfect Spot

  Stayed 7 days ending in March, 2022

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  a guest from Taunton, MA recommends this vacation rental

  This place was perfect for the four of us. Very clean and everything we needed for our vacation. Pool was crowded but served its purpose. Perfect location close to everything but far enough away to be peaceful I would rent again in a second
  Compass Realty on the other hand was fair at best. I looked for my key early (they are closed on Saturday which makes no sense to me) a woman came to the door which I did not knock on and asked me if I she could help me. I asked her if my key was available she said she would check but I could see her walk down the hallway and turn around. She came to the door and said no I asked when she said very rudely that check in was at 4:00 and closed the door. You are not very hospitable to be in the hospitality business. Wen I was at the pool I heard another man with a similar story. My advice is to rent this place directly from the ownership and skip Compass

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

  Stayed 7 days ending in March, 2022

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  Cyndi J from Virginia Beach, VA recommends this vacation rental

  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!

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• March in Old town Key West

  Stayed 7 days ending in March, 2022

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  Thomas H from Clinton, NY recommends this vacation rental

  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.

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• Look no further than the Truman Annex with Compass Realty

  Stayed 28 days ending in March, 2022

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  Sam S from South Bend, IN recommends this vacation rental

  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.

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• Everything is perfect in Paradise

  Stayed 7 days ending in December, 2021

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  Lisa P from Ashley, IL recommends this vacation rental

  What wonderful little condo! Very clean and comfortable. Super close to everything!

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• Thanksgiving Key west style....

  Stayed 8 days ending in November, 2021

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  Eric P from Palm Beach Gardens, FL recommends this vacation rental

  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.

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• Clean and well maintained

  Stayed 7 days ending in November, 2021

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  Tom V from Ansonia, CT recommends this vacation rental

  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.

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• Another Excellent Stay

  Stayed 10 days ending in August, 2021

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  Stephen K from Manchester, CT recommends this vacation rental

  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!

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• Had a great time

  Stayed 7 days ending in July, 2021

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  a guest from Ash Flat, AR recommends this vacation rental

  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.

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• Great place to stay!!

  Stayed 7 days ending in June, 2021

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  Sunny A from Townville, SC recommends this vacation rental

  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.

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• Terrific location

  Stayed 7 days ending in May, 2021

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  Theresa R from Delray Beach, FL recommends this vacation rental

  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.

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• Love the ship yard !

  Stayed 7 days ending in March, 2021

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  Jerome Z from Chardon, OH recommends this vacation rental

  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 !
  

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