SUN, SEA, AND SKY

Located in the desirable Truman Annex community, this beautifully maintained second-story Shipyard condo offers the perfect blend of island charm and modern comfort. Featuring one spacious bedroom with a king size bed, a small loft area with a sofa sleeper, a modern style living area, and a private balcony. This tropical retreat is ideal for a vacation escape to paradise. Nestled just steps from Duval Street, Fort Zachary Taylor Beach, and the Key West Historic Seaport, you’ll enjoy easy access to world-class dining, shopping, and entertainment—while still enjoying the quiet serenity of a gated community. The property is outfitted with washer/dryer, pots/pans, towels, linens, have central air conditioning, off street parking, and pool access.
Please note: This property requires a 28 night minimum stay.

Vacation Rental Reviews

• Vacation

  Stayed 14 days ending in January, 2026

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  Janice D from Sagamore Beach, MA recommends this vacation rental

  Great experience

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• Key west rental stay

  Stayed 9 days ending in November, 2025

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  Kyle A from Dartmouth, NS recommends this vacation rental

  The place was in good shape, close to everything you would need and want. Only thing is the A/C needs to be set on 73 which can be a little warm for some.

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• Amazing Property - Loved our stay!

  Stayed 7 days ending in June, 2025

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  a guest from Port Allen, LA recommends this vacation rental

  Wonderful condo in a fantastic location. The neighborhood is beautiful and well maintained. The condo has everything you need plus some extras! We loved it and keeping it on our list to return next year!

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• Perfect Property

  Stayed 7 days ending in January, 2025

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  Mark R from severna park, MD recommends this vacation rental

  Location is awesome. No rental car needed. Walking distance to stores, restaurants and attractions. Very Clean and well stocked. Neighborhood is quiet. Easy walk to Truman Waterfront Park, Duval Street, Faustos grocery store and Mallory Square for sunsets

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• Highly Recommend!

  Stayed 7 days ending in September, 2024

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  Monica L from Horseheads, NY recommends this vacation rental

  We were very pleased with our stay at Sun, Sea, and Sky. The place is the perfect Key West vacation spot. The unit is well kept and stocked with everything you need. We will definitely be back!

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• KW Vacation

  Stayed 7 days ending in July, 2024

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  Rebecca G from Beaumont, TX recommends this vacation rental

  We love the Truman Annex area. It is quiet and easy to walk to differentd areas.

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• Love This Place!!!

  Stayed 14 days ending in May, 2024

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  Dawn W from New York, NY recommends this vacation rental

  Our 2nd time staying here! Perfect space for the two of us; very clean and well-appointed; great location; helpful and responsive crew at the rental office.
  
  One minor note to owner: oven door handle and knobs could use tightening.
  
  Would definitely recommend this place... and we will be back!!!

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• OK condo that needs a little work but is quite comfortable

  Stayed 7 days ending in April, 2024

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  a guest from Saint Petersburg, FL recommends this vacation rental

  This was not located where we thought within the Annex. Defroster in frig was not working: water on shelves to wipe up every day and freezer filled with frost. Light bulbs out, no instructions on how to use washer, floors were dirty but everything else was very clean and comfortable. Had to brush teeth in kitchen sink due to such a small one in bathroom. But the rental price was great for this particular condo.

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• Sun, Sea and Sky❤️

  Stayed 7 days ending in April, 2024

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  Martha P from Bemus point, NY recommends this vacation rental

  We have stayed here many times and every year is better👍

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• Good location

  Stayed 7 days ending in February, 2024

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  Scott T from Stratford, ON recommends this vacation rental

  Excellent experience. Only comment is that it was advertised as having a ‘king’ sized bed and it does not (has a queen). We booked this rental based partly on having a king-sized bed.

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• So close to a perfect stay

  Stayed 7 days ending in January, 2024

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  a guest from East Greenbush, NY recommends this vacation rental

  First, the unit itself is very nice and on the second floor with a great balcony - and easy access to Duval Street and the waterfront. The only drawback to it is it fronts Southard Street which is NOT gated and busy enough to be noisy with traffic. Maybe it was the event in the park, but constant trucks, mopeds, gas powered golf carts, bikes, people, etc. Bring a noise machine and it can probably be drowned out, but the traffic was enough to wake up to each morning. Everything else was really nice - the cute corner bathroom sink could be larger but not a huge drawback. Good towels, nice tile shower, very well stocked kitchen. Mattress softer than my liking but nice. Pool was great. Access to 2 bicycles would be a great addition.

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• Nice Hide a way

  Stayed 7 days ending in December, 2023

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  Bryan S from Sagamore Hills, OH recommends this vacation rental

  Good Location . Very neat and clean excellent Lay Out.

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• Wonderful Property

  Stayed 7 days ending in November, 2023

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  JOSEPH G from NEW BRITAIN, CT recommends this vacation rental

  The Condo was in a perfect location to Duval Street, the Butterfly Conservatory, Aquarium, Mallory Square, Southernmost Point and just about everything else. Enjoyed our morning coffee on the rear deck which had foliage in the yard below to give some privacy from units across from us. The only negative was the lack of storage space for groceries and dry goods. Other than that we truly enjoyed it and would return!

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• Great place to stay

  Stayed 10 days ending in November, 2023

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  Lorraine B from Paget recommends this vacation rental

  Clean, bright, modern condo close to Duval and the boat race. Had many extras - take away coffee cups and extra pillows of different kinds! Lots of closet space and an extra room for storing luggage or optional sleeping area.

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• Perfect Unit

  Stayed 7 days ending in October, 2023

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  Alesia L from Phoenix, AZ recommends this vacation rental

  This unit was in a great location and was an easy walk to Duval Street. It was clean and came with everything you need to cook including spices and salt and pepper. There is a little nook that had a love seat pull out sleeper but if it is just 2 of you it's nice to put your luggage and store things out of the way. Very comfortable for a week-long stay. The bathroom sink is small but manageable and the shower was big which is more important. It was nice to have a washer and dryer as well. Very happy with our stay.

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• Key West Honeymoon

  Stayed 7 days ending in October, 2023

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  Michele S from Philadelphia, PA recommends this vacation rental

  My husband and I stayed for a week in Sun, Sea, and Sky for our honeymoon (10/09/23-10/16/2023). We are so glad we picked this condo for the week! It was everything we could have asked for and more. The condo is very clean, has all necessary amenities...coffee maker, dishes, washer/dryer, etc. We also loved the private deck. The location of the Truman Annex is perfect! Close to beaches, restaurants, Mallory Square and Duval. It feels secluded and quiet in the Truman Annex. The check-in process and checkout process were extremely easy. We enjoyed our time very much and would rent this condo again!

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• Great

  Stayed 7 days ending in September, 2023

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  Chuck B from Burlington, IA recommends this vacation rental

  We had a great time the rental was very clean and close to Duval street and all of the restaurants and bars. Truman Annex is a great location and a gated community. I would highly recommend this property.

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• Great Location! Well Stocked!

  Stayed 8 days ending in May, 2023

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  Benjamin W from Maysville, NC recommends this vacation rental

  Property was as described and as shown in photos. Property was well stocked. Location was great and area was quiet.

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• Loved it!

  Stayed 14 days ending in May, 2023

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  Dawn W from New York, NY recommends this vacation rental

  Great location. Property was very clean, well organized, well appointed and thoughtfully stocked. Enjoyed the extra sitting room and nice-sized terrace.

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• Key west condo

  Stayed 7 days ending in April, 2023

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  Nicola P from Belper recommends this vacation rental

  Fantastic accommodation and location.Only quibble was that we had a nightmare accessing the property.We arrived jet lagged and tired after an 8 hour journey tomfind that we couldn’t access the lock box-luckily we had help from someone who used to deal with the property and the door was open.Long story short-by trial and error managed to work out the lock box code-an incorrect digit had been entered.These things happen but we had no response from Compass to our e mails.This aside a fantastic condo beautifully decorated with lovely touches-best we,vie stayed in

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• Very nice condo in great location

  Stayed 7 days ending in April, 2023

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  Stephen H from Exeter, PA recommends this vacation rental

  Property description was accurate.Location excellent. Unit very clean and well-maintained.The only negatives were an extremely small bathroom sink with poor lighting for shaving, also poor lighting in kitchen area, mattress was squeaky every time you moved and the pillows were very flat causing severe neck pain.We ate all meals out so we did not take advantage of kitchen appliances or supplies.Very nice unit overall.Tried to rebook for next year but unit was booked by owner for our requested week.

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• A perfect get away

  Stayed 7 days ending in March, 2023

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  a guest from Ramsey, MN recommends this vacation rental

  Such a nice place to stay! The house was exactly as pictured, the location was amazing, the weather was perfection, and we even had a parking spot. Can’t wait to go back!

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• Great vacation

  Stayed 7 days ending in March, 2023

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  Martha P from Bemus point, NY recommends this vacation rental

  Very nice

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• Great stay

  Stayed 7 days ending in November, 2022

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  Charles E from DRYDEN, MI recommends this vacation rental

  Rental was clean, very functional with a the percent location for our stay. With the added East facing deck we had plenty of room to relax when a break was wanted. Didn’t cook anything since going out to eat in KW you have a 95% of enjoying where ever you pick to eat, rent is to high for bad restaurants to stay open. Like the perks of pool and beach towels along with the use of the cooler. Bathroom and shower no complaints.. bed could be slightly firmer but we slept fine every night. We’ve stayed in the Annex condos about 8/9times now this was a nice one.

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• Another wonderful stay!

  Stayed 14 days ending in October, 2022

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  Kathy J from Chester, MD recommends this vacation rental

  This was our third time at Sun, Sea and Sky so we felt right at home. Perfect location to walk anywhere within the Historic District and nice amenities. Near the fun but also a quiet place to relax and enjoy coffee on the deck. Having a parking space is wonderful. The electronic lock makes check-in/check-out a breeze.

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• Tru Vacay

  Stayed 7 days ending in October, 2022

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  Lynwood R from Kinston, NC recommends this vacation rental

  We enjoyed our stay here more than any place we have stayed in Key West. The booking process was easy, the cost was reasonable, and the location was perfect. The property exceeded our expectations in terms of having anything and everything we might need during our stay. The decor and furnishings made it comfortable and like home for us. We especially enjoyed having our morning coffee out on the balcony. We will definitely try to stay here again.

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• Fun in the sun

  Stayed 7 days ending in July, 2022

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  a guest from Urbana, OH recommends this vacation rental

  Centrally located. Quiet. Enjoyed our balcony and the pool. Loved the layout and decor. We had everything we needed during our visit.

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• Maycation

  Stayed 14 days ending in May, 2022

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  James S from Allentown, PA recommends this vacation rental

  We have spent a few years at this rental and truly enjoy the stay while we are in Key West!

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• The perfect rental

  Stayed 14 days ending in April, 2022

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  Kathy J from Chester, MD recommends this vacation rental

  This condo could not be in a more perfect location - beautiful and quiet surroundings within walking distance of virtually anything in the historic district. Near great restaurants, bike rental, the grocery store, pharmacies and only a block from the gorgeous Truman Waterfront Park. We have stayed there twice and have already booked again. The condo is well furnished with lots of extras - a good coffeemaker and nice heavy mugs, beach towels, etc. The porch is perfect for morning coffee and the pool is only a short walk away.

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• Great location

  Stayed 7 days ending in March, 2022

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  Holly B from Tigard, OR recommends this vacation rental

  Cozy condo in a great location! We love biking around Key West and this condo is located close to the beach, pier and the downtown area with lots of shopping and restaurants. Perfect size for 2 people.

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• A little piece of paradise

  Stayed 7 days ending in March, 2022

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  a guest from Poquoson, VA recommends this vacation rental

  Sun Sea & Sky was a beautiful place, clean and comfortable. During our visit the bedroom doors were broken and we were unable to open to let the fresh Key West air in. This was one of the main reasons we picked this place. However, that would be the only negative comment. Everything else was great! Highly recommend renting. The Truman Annex was also a beautiful area and in a perfect location.

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• Great condo in Key West

  Stayed 21 days ending in February, 2022

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  M Frank W from Ashburn, VA recommends this vacation rental

  We have been in this same condo for several years & we think it is (almost) perfect. The location, deck, size, kitchen, shower, are just great. The bathroom sink is a joke -- way too small. And the sofa in the living room is terribly uncomfortable, no matter where you sit. The ceiling fans & light/exhaust fan in bathroom need cleaning badly.

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• The best vacation ever!

  Stayed 21 days ending in October, 2021

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  Kathy J from Chester, MD recommends this vacation rental

  Very easy to book and all of my email questions were answered immediately. A great group to work with.

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• 3 Weeks in Paradise

  Stayed 21 days ending in May, 2021

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  James S from Allentown, PA recommends this vacation rental

  It was great visiting a free state! Beautiful weather and a great place to stay! Within walking distance of the beach as well as other major activities in the area.

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• Shipyard

  Stayed 7 days ending in April, 2021

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  Sue C from Danville, KY recommends this vacation rental

  I think this is the 16th time we have stayed at Truman Annex. We love staying at Shipyard Condos. It is within walking distance of every thing in old town, all of the condos in which we have stayed have been clean and nice and Compass Realty has provided great service. We already have a reservation made for our next visit.

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• Shipyard condo

  Stayed 14 days ending in April, 2021

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  Donna C from Oneida, NY recommends this vacation rental

  Sun,Sea,Sky was a very nicely appointed condo and we thoroughly enjoyed our stay. The condo was clean and would give all aspects a 5. Loved the location & would recommend. We've stayed in many condos in the shipyard and this one was one of the nicest.
  

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• Tropical Garden

  Stayed 8 days ending in November, 2020

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  Pascale H from Denver, CO recommends this vacation rental

  Beatiful setting, comfortable appartment, conveniently located, easy check-in/out. Parking, pool.

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• Such a beautiful place to stay.

  Stayed 11 days ending in October, 2020

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  Mike W from Senoia, GA recommends this vacation rental

  Our second time staying at The Shipyard and we loved it. Extremely clean and crisp. We had a great time with family we met in Key West.

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