See all properties
Condo

Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom

Photo gallery for Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom

Pool
Exterior
Room
Exterior
Interior

Reviews

9.6 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 4680 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪5 min walk‬
  • Place, Fort Zachary Taylor Historic State Park
    ‪8 min walk‬
  • Place, Mallory Square
    ‪9 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪14 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Twin Beds

Bedroom 3

1 King Bed

1 bathroom

Bathroom 1

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Outdoor play area

About this property

Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom

Welcome to Keys to Paradise – Your Cozy Retreat in the Heart of Key West!

Located in the charming Shipyard Condominium Complex at Truman Annex, this quaint and well-appointed first-floor condo offers the perfect blend of comfort and convenience. Featuring two bedrooms and one bathroom, it’s ideal for families or friends looking to explore Key West’s best attractions just steps away!

Inside Your Home Away From Home:

Spacious Living Area: Relax on new full-size sofa (sleeper included), two comfy chairs, and enjoy your favorite shows on the 50” flat screen TV.

Dining Room: Full-size table with seating for four—perfect for meals or game nights.

Fully Equipped Kitchen: Includes refrigerator, dishwasher, oven, coffee maker, blender, toaster, and all the essentials you need.

Guest Bedroom: Two twin beds that can convert into a king on request, a closet, dresser, full-length mirror, and a flat screen Firestick TV.

Master Bedroom: Queen bed, 50” flat screen TV, closet, dresser, and full-length mirror.

Bathroom: Full-size shower/tub combo, vanity, and toilet.

Laundry Closet: Washer, dryer, and cleaning supplies for your convenience.

Step Outside:

Enjoy a huge back deck with seating, a table, umbrella, and two cruiser bikes to explore the island. Lush, mature landscaping surrounds the condo, creating a serene environment with walking paths and easy pedestrian access through Truman Annex.

Community Perks:

Assigned parking spot right in front of your unit.

Secure gated community with code entry.

Pool area with loungers, towels, and restroom access.

Access to Truman Annex pedestrian gates via foot gate keys.

Prime Location:

Walk or bike less than 2 blocks to Truman’s Little Whitehouse and the iconic Green Parrot. Less than 1 mile from Fort Zachary Taylor Beach, Mallory Square, Duval Street, the Southernmost Point, Hemingway House, and more!

Leave your car behind and enjoy Key West at your own pace. Whether it’s your first visit or a beloved return, Keys to Paradise offers the ideal home base for your unforgettable island getaway.
Our prices include all fees. No hidden fees.

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Front Porch and Neighborhood
Villa Fleur at Shipyard Condominiums
Bahama Village
  • Pool
  • Kitchen
  • Washer
  • Dryer
9.8 out of 10, Exceptional, (51 reviews)
Villa Fleur at Shipyard Condominiums

House Rules

Check in after 4:00 PM
Minimum age to rent: 28
Check out before 10:00 AM
default

Children

Children allowed: ages 0-17
default

Events

No events allowed
default

Pets

No pets allowed
default

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
Long-term renters welcome
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock

About the neighborhood

Key West

Located in Old Town Key West, a neighborhood in Key West, this condo is near theme parks and by the sea. Fort Zachary Taylor Historic State Park and Ernest Hemingway Home and Museum 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. Kayaking and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby.
Map
Key West, FL

What's nearby

  • Duval Street - 5 min walk - 0.4 km
  • Florida Keys National Marine Sanctuary - 5 min walk - 0.4 km
  • Ernest Hemingway Home and Museum - 7 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Mallory Square - 9 min walk - 0.8 km

Getting around

  • Key West Intl. Airport (EYW) - 15 min drive

Restaurants

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

Frequently asked questions

Does Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom?

As of Apr 4, 2026, prices found for a 1-night stay for 2 adults at Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom on Apr 4, 2026 start from $263, 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.

Is Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom?

Check-in begins at 4:00 PM.

What time is check-out at Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom?

Check-out is at 10:00 AM.

Where is Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom located?

Located in Old Town Key West, this condo building is within a 10-minute walk of Truman Waterfront Park, Duval Street, and Fort Zachary Taylor Historic State Park. Ernest Hemingway Home and Museum and Florida Keys Beaches are also within 15 minutes.

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 29 out of 36 reviews
Rating 8 - Good. 5 out of 36 reviews
Rating 6 - Okay. 1 out of 36 reviews
Rating 4 - Poor. 1 out of 36 reviews
Rating 2 - Terrible. 0 out of 36 reviews

9.6/10

Cleanliness

8.0/10

Amenities

7.0/10

Property conditions & facilities

10/10

Check-in

9.6/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Moore F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay. The condo was clean and well supplied with towels, bikes and beach gear. We had no issues and would definitely recommend this to anyone who is looking for a place to getaway.
Stayed 7 nights in Jan 2026
Verified

10/10 Excellent

DAVID C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice place
Stayed 8 nights in Oct 2025
Verified

8/10 Good

Anita L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our two week stay at Keys to Paradise.Pros: location couldnt be better; walkable to everything, nice patio, bikes were a plus, comfortable mattresses, clean and well stocked.Cons: the unit could use a bit of an update; a bit "tired". Some new beach towels would be nice, another skillet and new microwave would be nice. A great addition would be a grill but I do understand its just another thing to have to care for. Overall it was a comfortable stay.
Stayed 14 nights in Jan 2026
Verified

10/10 Excellent

Laura S.

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

Wonderful Stay

Cute, clean condo and great location. Enjoyed it very much and would book again.
Stayed 9 nights in Oct 2024
Verified

10/10 Excellent

Anne B.

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

Cozy & close to a lot

Nice place, great location, enjoyed the stay, thanks.
Stayed 7 nights in May 2024
Verified

10/10 Excellent

Benjamin P.

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

Great Location

Very clean, modern and great location to everything you want to see. Four bikes on premises to use makes it extremely easy to explore.
Stayed 8 nights in Jan 2025
Verified

10/10 Excellent

Karen R.

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

Great Condo

This property is perfect for a small group. It was clean throughout and the back yard was nice to sit in the morning with our tea. Perfect location - can walk to everything!
Stayed 7 nights in Mar 2024
Verified

10/10 Excellent

Jan M.

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

Key West

Great location! Beautiful grounds! Nice condo with nice amenities! The owner was attentive to our needs!
Stayed 7 nights in Apr 2024
Verified

10/10 Excellent

Cheryl C.

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

Great

We had a great time!
Stayed 10 nights in Jan 2023
Verified

8/10 Good

Aaron P.

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

Location Location Location

Nice 2 bedroom ground floor condominium. Walking distance from Fort Zachary state park, Truman waterfront, and tons of restaurants and bars. Really nice backyard space, quiet and beautiful. Furniture and appliances are a bit dated but the grounds are great and well maintained. People are friendly and the location cannot be beat in Key West.
Stayed 21 nights in Feb 2025
Verified

10/10 Excellent

Kerri M.

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

Work vacation

Great time
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Lee O.

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

Nice christmas

Had granddaughters fly down for one of our three weeks. Great tome and great location.
Stayed 20 nights in Dec 2022
Verified

8/10 Good

Linda B.

Liked: Check-in, communication, location

Some improvements

Location is wonderful. Interior of unit needs some upgrades.
Stayed 9 nights in Feb 2024
Verified

10/10 Excellent

BRANDI S.

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

Great communication and clean unit

If you are looking for good communication, a clean unit and easy walking distance to Duval street. This is for you. Stayed for 9 nights.
Stayed 9 nights in Sep 2024
Verified

10/10 Excellent

Tiffani G.

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

Fantastic!

Truly the best location for exploring key west! We felt very safe and secure in this gated complex with our children. The grounds are beautiful, as is the condo! The bikes are a great bonus - as you will probably leave your car parked and just ride and explore everywhere! We will return to this condo without a doubt for our next key west fix!
Stayed 7 nights in Dec 2021
Verified

10/10 Excellent

Kerri M.

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

Mrs

Good
Stayed 8 nights in Aug 2023
Verified

6/10 Okay

Jeff G.

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

Anniversary Trip

The Shipyard Truman Annex was a great location for a seven day stay in Key West. The area is quiet, but close to all that is offered in Key West. If you enjoy walking, you can watch the sunrise in the morning, walk to a State Park, shop in the afternoon, have a nice dinner along the water, and watch a beautiful sunset in the evening. The condo was nice but had a few issues that will cause us to give the unit a overall score of 3.5. The queen bed in the master bedroom was horrible and we could survive one night in the bed. On the second night we tried the sleeper sofa and were forced out of the bed after one night due to another worn out mattress. By the third night we were forced to the second bedroom and used the twin beds for the rest of our stay. The condo provided bikes and beach chairs that we used on our trip to the State Park. The bikes are in need of minor work but served the purpose. The unit above ours had guests the first two nights and we could hear them into the early hours of the morning. After they left the unit was vacant the rest of the week and noice was not a problem. For our first time to Key West this area was enjoyable.
Stayed 7 nights in May 2023
Verified

10/10 Excellent

Diane R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice rental. Close to everything.
Stayed 21 nights in Feb 2026
Verified

10/10 Excellent

Nanci K.

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

Great place and location!

Near downtown and the beach at Zachary state park! Cute place. Nice patio.
Stayed 8 nights in Nov 2022
Verified

10/10 Excellent

Alexis B.

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

Great stay

Great place, great location, great stay!!
Stayed 7 nights in Nov 2022
Verified

10/10 Excellent

Paul S.

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

Wonderful

Would happily stay again
Stayed 7 nights in Oct 2022
Verified

10/10 Excellent

jeffry k.

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

Great Location

Convenient to everything. Nice pool. Bikes needed some work. Very clean. Enjoyed our stay
Stayed 7 nights in Oct 2022
Verified

10/10 Excellent

Les M.

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

Close to it all!

Excellent location close to everything we like. Safe area only a block from the courthouse. Good sized TVs and everything worked.
Stayed 7 nights in May 2022
Verified

10/10 Excellent

Dennis M.

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

Excellent property!

2nd visit. The cleanliness was superb. Also, appreciated the new washer/dryer, the beach chairs, bicycles, liquid hand soap at both kitchen (with new sponge) and bath, quality bath towels, beach towels, paper towels, and laundry and dish detergent. The only noticeable issue (which has nothing to do with owner) was the quality of the pool water which seemed dirty with little evidence of being circulated through filtration.
Stayed 9 nights in Apr 2022
Verified

10/10 Excellent

Pam S.

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

Great location, beautiful neighborhood

Best location on Key West - Walking distance to everything, and the state park beach was our favorite. The owner provided bikes, which was such a pleasant perk. The beds/bedding were comfortable. The only recommendation I have is for the owner to provide one or two more beach chairs, but that’s being me being picky.
Stayed 7 nights in Apr 2022

About the host

Hosted by Conch Collection

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback