TROPICAL VINEYARD

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. This 2nd floor 1 Bedroom recently renovated unit sits in the Shipyard area of Truman Annex. The primary bedroom has a queen size bed. Additionally there is a sleeper sofa in the living room. The French doors lead you to a very large balcony, perfect for dining, lounging and dreaming...
Please note: This property is monthly rental - the minimum rental period is 28 nights

Vacation Rental Reviews

• Great location and exceptionally quiet community

  Stayed 8 days ending in December, 2025

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  Deb P from Rogers, AR recommends this vacation rental

  Overall a very nice experience. The pros were a great management team and easy checkin and helpful check out
  Clean and liked the unit, had an updated bathroom and up to date kitchen with all essentials you would need to cook but no outside grill
  They also have a nice deck facing a palm trees and greenery, super relaxing
  Parking to the unit was right in front and an easy walk to most everything
  The unit is comfortable but furniture could use some updating
  Loved having a washer and dryer to wash towels and clothes
  WiFi and TVs were fine and bed is okay
  The stairs are a challenge especially with luggage so if you have knee issues it might be a concern
  Pool is dated but close to unit...better to go to Ft. Zachery
  If you are staying a while you will need to stop at Publix for extra toilet paper and soap etc
  Overall happy with the visit to tropical vineyard

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• Tropical Vineyard

  Stayed 7 days ending in October, 2025

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  Sharon M from Edinburg, PA recommends this vacation rental

  Rental was great. Clean and spacious and very quiet. We are very disappointed that weekly rentals are not going to be offered in the Annex any longer. This is our favorite place to stay when vacationing in Key West.

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• Beautiful Key West-Not so Beautiful Accommodatios

  Stayed 7 days ending in May, 2025

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  a guest from Greenwood, IN does not recommend this vacation rental.

  Michelle with Compass was very helpful. Love the location, but state of property is worn and unclean. Kitchen seemed the best, bathroom was updated but not clean. Shower was not draining, but Compass addressed and resolved quickly. There were only 2 washcloths for 2 people for an entire week; not good. Bed was very uncomfortable and noisy with any movement. There was wifi, but both TV's would not allow you to pick channels; guide would come up, but would not respond when a channel was picked. No TV for the week, but not the end of the world in paradise. Ceiling fans and lights were very dirty. Would not stay in this unit again, nor would I recommend to anyone.

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• Great

  Stayed 21 days ending in May, 2025

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  Petra K from Ludwigshafen am Rhein recommends this vacation rental

  Perfect place

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• Tropical Vineyard

  Stayed 14 days ending in March, 2025

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  a guest from Glen Cove, NY recommends this vacation rental

  We've been staying at this residence for many years. It is in a good location. Everything is within walking distance. The bathroom was remodeled three years ago which improved the unit greatly. We intend to return next year.

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• Sunny week in Key West

  Stayed 7 days ending in March, 2025

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  a guest from Cumming, GA recommends this vacation rental

  We had a wonderful week in Key West! The weather was great, we loved the Truman Annex area and so much to do. The food is delicious, so many restaurants to choose from. The key lime pie is to die for!
  
  As far as the check in to our unit, it was not very clear. When we went to look for lock box it wasn't there. Finally at 4pm someone came to the office to hand them out. The unit it self was nice. I would give it a 6! It needed some TLC, the furniture was worn, floor not very clean, walls needed paint, bed was horrible, dirty ac vents and ceiling fans, hole in blankets and pillows were flat. Bathroom was very small.
  
  We really liked the area (the truman annex) but I wouldn't stay in this unit again. I would try a different one.
  
  The last thing is we came back to condo one day to find both locks locked and we only locked one and our keys were giving us trouble to open it. I was able to get another key by the management company and was told that the monthly pest control had come in to spray. I was never told about this. They said I was emailed but I don't check emails on vacation and when I did check there was NO email. They had my cell and didn't text!!!!!

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• Wonderful 2 week stay

  Stayed 14 days ending in March, 2025

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  Sue C from Danville, KY recommends this vacation rental

  We have stayed in Tropical Vineyard a couple of times before this one. Since our first stay, it had been updated. A new bathroom, a new kitchen, new flooring and new paint made the stay very pleasant. While the condo is smaller than some of the Shipyard condos in Truman Annex, it is still very nice. It has a roomy balcony and is is extremely well located. My only complaint is that the living room furniture is not very comfortable. However, I would recommend it to others.

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• Tropical Vineyard in Shipyard.

  Stayed 14 days ending in January, 2025

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  James F from Indianapolis, IN recommends this vacation rental

  This was our fifth year staying in a Shipyard condominium. Beautiful ambience and experience in the Truman Annex in Old Town.

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• Another great vacation

  Stayed 7 days ending in November, 2024

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  Alexander D from Elizabeth, PA recommends this vacation rental

  Oscar and Tracy are great to deal with. Thank You! The condo was spotless! Close to everything. Another enjoyable week in Key West

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• Truly Tropical

  Stayed 9 days ending in November, 2024

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  Debra S from Hanover, MN recommends this vacation rental

  Absolutely love this location. We walked everywhere, great way to get our steps in. The property management was very helpful and we had one small maintenance issue that was taken care of same day. Newly remodeled bathroom was very well thought out and beautiful.

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• Nice place close to Duval Street

  Stayed 7 days ending in March, 2024

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  a guest from Rochester Hills , MI recommends this vacation rental

  Nice place to stay, close to the pool and within walking distance to many places. Unit could use some minor touch up from normal wear and tear.

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• Tropical Vineyard

  Stayed 14 days ending in March, 2024

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  a guest from Glen Cove, NY recommends this vacation rental

  We've been renting this place for the last few years. It is well located and reasonably clean. Had to clean the coffee pot. The shower was clogged, so I had to unclog it myself which was pretty disgusting. It is obvious that the house cleaners had to be aware of this before they left. The new bathroom installed last year improved the space a great deal. Plan on renting again next year.

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• Wonderful Key West rental

  Stayed 7 days ending in February, 2024

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  a guest from Naperville, IL recommends this vacation rental

  We truly enjoyed staying at Tropical Vineyard. It’s in a very desirable location- close to all the excitement of the downtown area but enough of a distance so you don’t hear the noise at night. Also close to Ft Zachary beach - we rode bikes there every day. The condo was very clean and comfortable and had everything we needed. The mattress was on the soft side which is not our preference. There was an abundance of hangers in the closet and plenty of storage space for clothes which is rare for a rental. We made breakfast and lunch at the condo most days but always had dinner out. There are so many great restaurants within walking distance. Check on/out process was very easy. The management company provided all the needed info in an email as well as on the Hospitality app. We will definitely stay at this condo again.

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• Enjoyed the stay at Tropical Vineyard.

  Stayed 7 days ending in January, 2024

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  a guest from Lawrenceville, PA recommends this vacation rental

  Very clean property, well equipped. Once we parked did not have to move our car for a week. Close walk to everything.

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• Nice property, great location

  Stayed 7 days ending in November, 2023

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  Stephen H from Fort Myers, FL recommends this vacation rental

  Great location in Shipyard, nice clean accommodations. Flatware was minimal, could use more forks, knives, spoons. Only negative, deck in back was in landing zone for iguana poop who made his home in palm tree above us. Would be nice if HOA would amend rules to allow pets. People in management office were very friendly and helpful.

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• Tropical Vineyard

  Stayed 9 days ending in November, 2023

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  Lynwood R from Kinston, NC recommends this vacation rental

  This property is ideal for two people. It is located within walking distance of Old Town. Having a place to park the car is wonderful. The property was clean and well-maintained. We loved sitting out on the balcony in the mornings. We attended the airboat races and enjoyed the proximity to the park where the boats were located.

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• Joseph Lilly Review

  Stayed 7 days ending in August, 2023

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  Joseph L from East Rockaway , NY recommends this vacation rental

  Shower Drain was slow and got slower as the week went.

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• 210-10

  Stayed 7 days ending in March, 2023

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  audrey r from ORCHARD PARK, NY recommends this vacation rental

  Would definitely stay here again. It would have helped to have a list of what we would/ would not find at the apt. ( soap, toilet paper, bikes
  / blow dryer etc).
  Overall it was a very nice place to stay. Thank you.
  

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• Tropical Vineyard

  Stayed 7 days ending in March, 2023

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  a guest from Glen Cove, NY recommends this vacation rental

  We have been staying at this unit for years. Slowly, the owner has been been doing updates to the apartment. However, when we arrived this year, The owner renovated the bathroom which made the unit much more enjoyable. Will be back again next year.

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• Keys Getaway

  Stayed 14 days ending in March, 2023

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  Deborah G from Springfield, OH recommends this vacation rental

  This is a nice property for 2 people. Back porch was great! New bath room was very nice. Shower was slow then clogged but maintenance came when called. All in all a good stay. Would recommend updating the Bed linens & comforter. Also the front room furniture is dated and not very comfortable.

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• Tropical Vineyard

  Stayed 7 days ending in January, 2023

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  Mark M from Saint Joseph, MI recommends this vacation rental

  Furniture is a little dated but very clean and great location.

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• Our Stay at Tropical Vineyard

  Stayed 9 days ending in July, 2022

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  Scott W from Virginia Beach , VA recommends this vacation rental

  Overall, we enjoyed Tropical Vineyard. We are frequent travelers to Key West, but have never stayed on Truman Annex. The location is excellent for getting to both the beach at Ft. Zach and the bars and restaurants of Old Town. The condo was clean and offered plenty of room. The only downsides were 1) a number of lights did not work (may have just needed bulbs), 2) the ice maker worked, but was probably on its last legs. The ice would freeze up in the tray. 3) a couple of nights when we were sitting on the deck, a neighbor would come out on his deck and smoke, driving us inside. We would stay on Truman Annex/Shipyard gain though.

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• Tropical vineyard stay

  Stayed 7 days ending in June, 2022

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  a guest from Elmont, NY does not recommend this vacation rental.

  Place was clean. Updated kitchen. Bathroom could use update. Couch is old and hard to get up from. Would recommend this place if updates were done.

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• Shipyard Condos Truman Annex

  Stayed 21 days ending in April, 2022

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  Mark J from Steamboat Springs , CO does not recommend this vacation rental.

  Great location. This condo needs to clean the grout or replace grout in bathroom; put new bathroom rugs/mats(they looked dirty); in the kitchen it would be nice to have garbage bags, dishwater pods; the deck was dirty, the AC lines should be covered, the wall had someone recaulk the windows and had black finger marks all around the white window trim, it would be nice to have some type instructions for the TVs. When you pay $7500 for three weeks the place should be spotless.

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• Tropical Vineyard

  Stayed 7 days ending in March, 2022

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  a guest from Glen Cove, NY recommends this vacation rental

  This is the 4th time we've stayed at this location. We enjoy it because it is in a good location to enjoy the Key West Experience. We have stayed at many Truman Annex units over the last 20 years and enjoyed them all. The only thing I notice over the last 20 years is that the units definitely can use some updating. Painting, bathroom upgrades, annual professional cleaning etc. The age is starting to show. That being said, since you spend so little time in the unit, it's not that important. I will definitely be back next year.

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• Key West Vacation

  Stayed 7 days ending in March, 2022

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  a guest from North Rose, NY recommends this vacation rental

  First time in Key West, loved it. Great location.

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• Redo needed

  Stayed 7 days ending in February, 2022

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  Peter P from Casnovia, MI does not recommend this vacation rental.

  Layout was goo. However, the furniture is tired as are the cushions in the couch as well as the matras. The floor was filthy and we had to clean it on day 1. The agency returned our cleaning fee.

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• Key West Truman Annex

  Stayed 7 days ending in January, 2022

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  a guest from Morrow, OH recommends this vacation rental

  The Tropical Vineyard Unit in the Truman Annex is the perfect location for stay in Key West. Very close to Duval and the surrounding area, everything was an easy walk. All that Key West has to offer - restaurants, bars, shops, museums, the beach, bike rentals, etc. is at your fingertips.

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• Great Location, Tired Condo

  Stayed 9 days ending in November, 2021

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  a guest from Ogunquit, ME does not recommend this vacation rental.

  Great location close to Duval St. Most uncomfortable bed I've ever tried to sleep on. Needs replacement! Tub/shower was old & stained. Deck very dirty and needs power washing. Living room furniture old and uncomfortable. Kitchen is updated and nice. Very nice pool and grounds.

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• Wonderful Stay at Tropical Vineyard

  Stayed 7 days ending in October, 2021

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  SHARON S from Somerdale, NJ recommends this vacation rental

  Beautiful property with great balcony. The kitchen was very well stocked and having towels for bathroom and beach towels was perfect. We even used the beach chairs to go to Fort Zachary beach. The air conditioning worked well and made it comfortable to sleep. The only change I would suggest is better pillows for the bed. The pool was wonderful and pretty much just steps away :).

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• Grteat location!

  Stayed 7 days ending in September, 2021

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  Ted Y from Twinsburg, OH recommends this vacation rental

  We had a wonderful time and the condo worked out perfect for our stay. The management staff was very accommodating and helped us with a later check out due to a late flight out of KW. We would definitely stay here again!

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• Tropical Oasis

  Stayed 7 days ending in June, 2021

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  a guest from Stamford, CT recommends this vacation rental

  Great location - convenient to Duval St, Zachary Taylor state park and other attractions. Truman Annex is picturesque, quiet, well cared for and close to all the action. Most attractions within walking distance. Unit itself was bright and cheery and is perfect for two. Property management company was very responsive and accommodating of our early check-in request and late check-out. Only reason I didn't give an overall 5 rating was the cleanliness of the unit upon arrival. A number of dishes/glasses were dirty and bathroom cleanliness wasn't great - especially the floor. Would definitely stay in this unit again.

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• Key West Stay

  Stayed 7 days ending in June, 2021

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  Karen P from Inola, OK recommends this vacation rental

  The rental was good, I had to pick up keys after hours-light by the lock boxes would be helpful.

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• Would definitely stay here again!

  Stayed 14 days ending in May, 2021

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  Dawn W from New York, NY recommends this vacation rental

  Great property for two of us, at a great price; perfect location; management team very responsive!

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• Key West Vacation Rental

  Stayed 7 days ending in April, 2021

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  a guest from Apollo, PA recommends this vacation rental

  The rental was very nice and close to Truman Waterfront Park. Good location and was the perfect size for a party of two for a week stay. The unit was clean and well kept however we did have a couple of issues. First the TV in the living room did not work properly. The picture quality was very bad the color was mostly red. Second two of the days we had a worker on our balcony doing repairs. One morning I was unable to go out on the balcony to sit due to the repair man with a ladder using it. The next day they were gone but the balcony was very dirty so we no longer used it. Other than those two issues it was very nice.

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• Love the Shipyards, not the unit

  Stayed 7 days ending in April, 2021

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  Diane B from Mount Carroll, IL does not recommend this vacation rental.

  This is our 10th year of coming to Key West and we have always stayed in the Truman Annex and booked through Compass Realty. We love the shipyards area but were very disappointed in our unit this time. The kitchen was fine but the bathroom was in rough condition - it had visible mold and soap scum on the old shower doors and tiles; the bathroom sink leaked and a plumber had to be called to put in a new faucet and the toilet flushing mechanism was unpredictable. The screen on TV in the living room went blank on the 3rd day and when it finally came back it had weird lines through it for the rest of the time we were there. The deck was unusable due to right side being wide open to the unit next door without a privacy screen and they used theirs on a regular basis for smoking & all meals which meant we couldn’t use ours. The unit on the whole was less than satisfactory to say the least.

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• Tropical Vineyard

  Stayed 7 days ending in March, 2021

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  a guest from Glen Cove, NY recommends this vacation rental

  We really enjoyed staying at Truman Annex. We have probably stayed at different locations 10 - 15 times over the last 15 years including units at Porter's Lane, Porter's Court and others. This is the 3rd time we've booked Tropical Vineyard. The first time we stayed there we were very happy with the accommodations, but made commented that the bath/shower was very slippery and the bathroom sink needed a new faucet. In fact, the owner had a journal asking guests to comment about the unit. The biggest complaint by most of the responders was the bathroom. The 2nd time we rented it, when we arrived, we were told renovations were going on and were moved to a lovely unit on Southard St. by the guardhouse. When we arrived last Saturday we were excited to see the renovations expecting to see a new bathroom. Though the renovations made the unit nicer, the bathroom was the same. In fact, the faucet on the bathroom sink was worse. My only recommendation is the bathroom be updated. That being said, I would consider staying at the Tropical Vineyard on our trip to Key West next year.

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• Key West Getaway

  Stayed 28 days ending in February, 2021

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  Dorothy K from Chicago, IL recommends this vacation rental

  I enjoyed my stay at Tropical Vineyard.

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• Tropical Vineyard

  Stayed 7 days ending in November, 2020

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  John W from Lynn, MA recommends this vacation rental

  All of Truman Annex is in a great location. Within walking distance to everything from Old Town / Seaport, Southernmost Point, even the Cemetery.
  The unit appeared to be in the process of being remodeled. The kitchen is new, bathroom outdated, but no issues.
  Had a slight issue with the A/C Unit upon arrival, only reason I mention this is to give Kudos to Compass Realty, they called an HVAC guy after hours and he came right out and replaced the capacitor, Compass Realty has always been VERY accommodating to our needs, not just when there is an issue like this (only time we’ve had an issue), but also in allowing early check ins and late check outs, etc whenever possible.

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