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Tropical Vineyard at The Truman Annex in Key West

Photo gallery for Tropical Vineyard at The Truman Annex in Key West

Living area
Living area
Outdoor dining
Outdoor dining
Living area

Reviews

9.2 out of 10
Wonderful
1 bedroom1 bathroomSleeps 453.9 sq m

Popular amenities

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

Explore the area

View map
Key West, FL
  • Place, Florida Keys National Marine Sanctuary
    ‪5 min walk‬
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪6 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪13 min drive‬

Rooms & beds

1 bedroom (sleeps 4)

Bedroom 1

1 Queen Bed

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio

About this property

Tropical Vineyard 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. 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

Add dates for prices

Amenities

Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
Parking available

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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. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. USCGC Ingham Maritime Museum and Florida Keys Eco - Discovery Center are also worth visiting.
Map
Key West, FL

What's nearby

  • Florida Keys National Marine Sanctuary - 5 min walk - 0.4 km
  • Duval Street - 6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum - 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

Getting around

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

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Willie T's - ‬6 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Rams Head Southernmost - ‬7 min walk

Frequently asked questions

Is Tropical Vineyard 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 Tropical Vineyard at The Truman Annex in Key West?

As of 28 March 2026, prices found for a 1-night stay for 2 adults at Tropical Vineyard at The Truman Annex in Key West on 23 April 2026 start from NZ$239, 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 Tropical Vineyard at The Truman Annex in Key West?

On-site parking is available at the property.

What time is check-in at Tropical Vineyard at The Truman Annex in Key West?

Check-in begins at 4:00 PM.

What time is check-out at Tropical Vineyard at The Truman Annex in Key West?

Checkout is at 10:00 AM.

Where is Tropical Vineyard 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 Ernest Hemingway Home and Museum. Florida Keys Beaches and Mallory Square 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. 33 out of 53 reviews
Rating 8 - Good. 16 out of 53 reviews
Rating 6 - Okay. 2 out of 53 reviews
Rating 4 - Poor. 2 out of 53 reviews
Rating 2 - Terrible. 0 out of 53 reviews

9.2/10

Cleanliness

9.2/10

Check-in

9.2/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

8/10 Good

Petra K.

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

Perfect place

It was just great
Stayed 13 nights in Apr 2024
Verified

10/10 Excellent

Debra K.

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

Tropical Vineyard

We always stay at the Shipyard because of it great location! Never disappoints!!
Stayed 7 nights in Oct 2023
Verified

10/10 Excellent

Apex Custom W.

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

Nice place close to lots of things

Great location, close to Duval St. And lots of other things. Property was nice but could use a little TLC on minor wear and tear.
Stayed 7 nights in Mar 2024
Verified

10/10 Excellent

James B.

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

Great place. Great location!

Was just a couple blocks from the center of Duval Street. Could walk everywhere. Quiet. Very nice location.
Stayed 7 nights in Jun 2022
Verified

10/10 Excellent

NICOLE K.

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

Beautiful Property & Perfect Location

We loved everything about our vacation from beginning to end! The check in/out process was seamless, the condo was very clean/comfortable & had all of the accommodations to make you feel at home for a week. The property itself, was very well maintained with an awesome pool that we used daily! We were only two blocks away from all of the action on Duval street & could easily retreat back to our condo when we were ready for a little quite time. Can't wait until our next visit!
Stayed 7 nights in May 2024
From a partner site

10/10 Excellent

Al D.

Another great vacation

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

10/10 Excellent

Mark M.

Tropical Vineyard

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

10/10 Excellent

Connie W.

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

Great place to stay

This upstairs apartment/townhome was great for two people. It was in a great location for walking downtown. The apartment was very clean. The only thing that needs to change would be the bed. The mattress was old and sunk in the middle. The frame it was on felt like it was going to collapse at anytime. Other than that everything was great.
Stayed 7 nights in Oct 2023
From a partner site

10/10 Excellent

Philip S.

Tropical Vineyard

Rating Details: The property manager was more than 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: 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.
From a partner site

10/10 Excellent

Steve H.

Nice property, great location

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: 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.
Stayed 7 nights in Nov 2023
Verified

8/10 Good

Deb P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We always wanted to stay at the Truman Annex and this was the last month for weekly rentals…now the TA will go to monthly onlyThe likes are-wonderful location close to beach and close to Duval and once on the compound you feel secluded The Management team was a 5 star, easy to reach and very good instructions about getting into the unit and additional details on staying at the unit and helpful when we checked out…big thanks!The reserved parking space was right at the front door and convenient The kitchen has nice appliances and essentials if you want to cook and was very clean (no outdoor grill)The bathroom has been update and nice walk in showerLoved having a washer and dryer The outdoor deck sits right over a nice courtyard setting and is large TV’s and WiFi were fineNever heard any noise or neighbors Some tips- you might need to make a run to Publix for toilet paper and paper towels, plus bring your own bath soap…only 2 wash clothes but there were more towels The unit is on the 2nd floor and the stair are a workout especially with luggage The living room furniture and bedroom are needing an update but over all everything was cleanThe pool was cool and no heat and it looks pretty dated but plenty of chairs and close to the unit If you come in late make sure to really read the check in instructions to find the office as it can be a bit hard to see it when dark out.Over all we had a nice week and hope to stay in the Annex again but on a first floor level.
On the deck
Stayed 8 nights in Dec 2025
From a partner site

10/10 Excellent

Thomas R.

210-10

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: 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.
From a partner site

8/10 Good

JAMES S.

Wonderful Stay at Tropical Vineyard

Rating Details: The property manager was more than 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: 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 :).
From a partner site

10/10 Excellent

Deborah s.

Keys Getaway

Rating Details: The property manager was adequately 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: 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.
From a partner site

8/10 Good

A guest from Virginia Beach, VA

Our Stay at Tropical Vineyard

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: 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.
From a partner site

10/10 Excellent

Debra S.

Truly Tropical

Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: 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.
From a partner site

10/10 Excellent

Philip S.

Tropical Vineyard

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: 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.
From a partner site

10/10 Excellent

Sue K.

Wonderful Key West rental

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 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.
From a partner site

10/10 Excellent

James B.

Enjoyed the stay at Tropical Vineyard.

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

10/10 Excellent

Ruth H.

Tropical Vineyard

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 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.
From a partner site

10/10 Excellent

Joseph L.

Joseph Lilly Review

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

8/10 Good

mary e.

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

Nice place

A nice place to stay and close to Duval! The place is only big enough for two people !
Stayed 9 nights in Oct 2022
Verified

10/10 Excellent

Claudia E.

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

Convenient location

Super convenient to Mallory Square, the beach at Ft Zachary, and anything else you could want in Key West. Would deff stay here again!
Stayed 7 nights in Jul 2022
From a partner site

6/10 Okay

A guest from Elmont, NY

Tropical vineyard stay

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 do not recommend this vacation rental. Reviewer Comments: 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.
From a partner site

8/10 Good

Philip S.

Tropical Vineyard

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: 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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