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Tropical Vineyard at The Truman Annex in Key West

Condo near Duval Street in Key West

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

Pool
Terrace/patio
Exterior detail
Living area
Interior

Reviews

9.2 out of 10
Wonderful

Entire condo

1 bedroom1 bathroomSleeps 4580 sq ft

Popular amenities

  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space
  • Parking available

Explore the area

View in a map
Key West, FL
  • Place, Florida Keys National Marine Sanctuary
    ‪5 min walk‬
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Fort Zachary Taylor Historic State Park
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪15 min drive‬

Room options

About the neighborhood

Key West

City center stay.Within a 10-minute walk of this Old Town Key West condo, you'll find Duval Street and Ernest Hemingway Home and Museum. Florida Keys Beaches and Mallory Square are also within half a mile (1 km).
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What's nearby

  • Florida Keys Eco - Discovery Center - 3 min walk - 0.2 miles
  • Florida Keys National Marine Sanctuary - 5 min walk - 0.3 miles
  • Duval Street - 6 min walk - 0.4 miles
  • Ernest Hemingway Home and Museum - 8 min walk - 0.4 miles
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.4 miles

Getting around

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

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Moondog Cafe & Bakery - ‬8 min walk
  • ‪Rams Head Southernmost - ‬7 min walk

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

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

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Jun 7 - Jun 8
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Property amenities

Pool/Spa

  • Communal pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Parking on site

Food and drink

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop

Bedrooms

  • Bedroom
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Shower
  • Towels provided

Living spaces

  • Living room

Outdoor areas

  • Patio

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Gated community
  • Unit size: 580 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

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
Onsite 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher and a smoke detector in each accommodation.

Property is also known as

Tropical Vineyard @ the Truman Annex
Tropical Vineyard in the Truman Annex
Spectacular Price ) Tropical Vineyard @ the Truman Annex
20% Off Summer Special Tropical Vineyard @ the Truman Annex
2698-193347

Frequently asked questions

How close is Tropical Vineyard at The Truman Annex in Key West to the airport?

This condo is 4.1 mi (19-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Tropical Vineyard at The Truman Annex in Key West have an airport shuttle?

Airport shuttle services are not available at this condo.

How close is Tropical Vineyard at The Truman Annex in Key West to the beach?

This condo is a short 12-minute walk from Florida Keys Beaches and 0.8 mi (8-min drive) from South Beach. Don't forget your sunscreen!

Does Tropical Vineyard at The Truman Annex in Key West offer free breakfast?

This condo does not offer free breakfast.

Is there a casino at Tropical Vineyard at The Truman Annex in Key West?

No, there is no casino at this condo.

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

Check-in begins at 4:00 PM.

Is there free parking at Tropical Vineyard at The Truman Annex in Key West?

Free parking is not available at this condo.

Does Tropical Vineyard at The Truman Annex in Key West have a pool?

This condo does not have a pool.

Does Tropical Vineyard at The Truman Annex in Key West have a spa?

There are no spa services available at this condo.

How close is Tropical Vineyard at The Truman Annex in Key West to downtown Key West?

This condo is 0.2 mi away from Key West.

Tropical Vineyard at The Truman Annex in Key West Reviews

Reviews

9.2

Wonderful

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

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

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.
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
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
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.
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

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

John W.

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: 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.