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Condo

MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West

Photo gallery for MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West

Beautifully Designed Kitchen with all stainless steel appliances.
This kitchen is fully equipped with pots, pans and Breakfast Bar.
In fact the entire condo has been remodeled and it is very accommodating.
The Living and Dining Area
The Living Room has French doors that open onto the rear deck.

Reviews

10 out of 10
Exceptional

Highlights

  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Duval Street
2 bedrooms1 bathroomSleeps 5

Popular amenities

  • Heated pool
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue

Explore the area

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

Rooms & beds

2 bedrooms (sleeps 5)

Bedroom 2

2 Single Beds

Master Bedroom

1 Queen Bed

1 bathroom

Bathroom 1

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Garden
Dining area

About this property

MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West

This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorated. Fresh paint throughout, all new hardwood flooring, new kitchen with granite counter tops, stainless steel appliances, and brand new designer furnishings make this a home away from home. A large rear courtyard with a wood sun deck and outdoor grill is perfect for entertaining. Located in the heart of old town Key West, Truman Annex is a gated community of private homes and condominiums. There is an inviting heated swimming pool on premises.

All dining, shopping, and night life are within walking distance from your door. One of the highest-rated national park and beach area in America is just a short walk away. The Master bedroom has a Queen size bed. 2nd bedroom has 2 single beds. There is a studio couch in the living room. This unit is fully equipped for long, enjoyable stays. All you need is your clothes and toothbrush. Life is good in the Keys!

Walk to the beach, gorgeous sunsets and all of the attractions that Old Town Key West has to offer.

Tons of restaurants and bars are within walking distance.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 26
Check out before 11:00 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
Renters must make voice contact with owner within 72 hours after booking. Owner will send renter a rental agreement that must be signed

Important information

You need to know

Property # 3956691
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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Key West

Located by the sea, this condo is in Old Town Key West, a neighbourhood in Key West. Southernmost Point 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. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
Map
Key West, FL

What's nearby

  • Duval Street - 4 min walk - 0.4 km
  • Florida Keys National Marine Sanctuary - 6 min walk - 0.6 km
  • Ernest Hemingway Home and Museum - 8 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park - 9 min walk - 0.8 km
  • Mallory Square - 12 min walk - 1.1 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 14 min drive

Restaurants

  • ‪Green Parrot Bar - ‬5 min walk
  • ‪Margaritaville - ‬8 min walk
  • ‪Blue Heaven - ‬9 min walk
  • ‪Mangoes Restaurant - ‬8 min walk
  • ‪La Concha Bar - ‬8 min walk

Frequently asked questions

Does MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

How much does it cost to stay at MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West?

As of 6 June 2026, prices found for a 1-night stay for 2 adults at MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West on 19 August 2026 start from NZ$486, 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 MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West pet-friendly?

No, pets are not allowed at this property.

How much is parking at MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West?

On-site parking is available at the property.

What time is check-in at MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West?

Check-in begins at 4:00 PM.

What time is check-out at MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West?

Checkout is at 11:00 AM.

Where is MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, 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 Florida Keys Beaches. Fort Zachary Taylor Historic State Park and Ernest Hemingway Home and Museum are also within 10 minutes.

Reviews

10

Exceptional

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. 187 out of 192 reviews
Rating 8 - Good. 5 out of 192 reviews
Rating 6 - Okay. 0 out of 192 reviews
Rating 4 - Poor. 0 out of 192 reviews
Rating 2 - Terrible. 0 out of 192 reviews

10/10

Cleanliness

8.8/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

William S.

Liked: Cleanliness, check-in, communication, listing accuracy
Just a fantastic week with all the comforts of home. Easy walking the historic area.
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Mari T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was welcoming and communication was great. The condo is wonderful and a great location.
Stayed 7 nights in Jan 2026
Verified

10/10 Excellent

Jacob N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location, extremely gracious host.
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

michael l.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was beautiful lovely place. Location was great best place I have stayed at
Stayed 14 nights in Jul 2025
Verified

10/10 Excellent

Hilary B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay and everything we needed for an awesome family vacation in Key West! The location was perfect and very walkable to everything!
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Doug Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice place. Close to everything, very convenient.
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

richard m.

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

Fantastic condo

Real nice place and everything was great.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Vicky S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fully equipped kitchen but we didn't cook in but definitely can if you choose to. We love the location and feel safe in Truman Annex. It was comfortable for us four adults.
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Gregg S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This condo was ideally located. Very clean and well equipped. Nicely decorated and remodeled. Truman Annex is quiet and safe yet only a few minutes walk from all the action on Duval St. Our hosts thought of everything, making it easy to access the place, park, and enjoy the community amenities. Our communication with Jim was outstanding and he reached out ahead of trip to make sure we had everything we needed.
Stayed 7 nights in Jan 2026
Verified

10/10 Excellent

Christine K.

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

Vacation in Key West

Highly recommended. Perfect accommodations in a perfect location!
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Joan C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Thank you for a most awesome week at your place...so close to everything on our bucket listand our surroundings wetr peaceful and beautiful Thanks Jim for being so accommodating to our needsJoan & Nina
Stayed 7 nights in Sep 2025
Verified

10/10 Excellent

Jessica B.

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

Nice little spot in the Truman Annex

We enjoyed our stay. Great location!
Stayed 7 nights in Apr 2023
Verified

10/10 Excellent

Julia B.

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

Felt like home

Conveniently located and quiet.
Stayed 7 nights in Jan 2025
Verified

10/10 Excellent

Thomas G.

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

Majestic Paradise is a Great Condo!

The property is in a great location. The pool is awesome and the condo very comfortable!
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

Lisa P.

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

Parrott Heads

Place was clean, great location, stocked with everything you need on vacation!
Stayed 7 nights in Feb 2025
Verified

10/10 Excellent

Verified traveller

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

Great Condo

We had a great stay at this condo. Good location to all the activity and the complex is beautiful.
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Jessie C.

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

Beginning of Truman

Great walking distance to everything. You are in the middle of it all at this location. Fantastic temporary home away from home.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Lorraine B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything ready for a good visit. Great location, near to downtown Key West. Taxi and Uber readily available. Foilage at condo stunning. We are return visitors and it never disappoints. Thank you Jim and Colleen! Hoping to return.
Stayed 21 nights in Sep 2025
Response from VrboOwner on 12 October 2025
Thank you. Please come visit again you are great guests!
Verified

10/10 Excellent

Lora E.

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

Key West Trip

Property was conveniently located to everything
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Pam C.

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

Clean and cozy, convenient to everything. Great hosts.

Clean and cozy, convenient to everything. Quiet and beautiful back deck. Hosts great and informative.
Stayed 7 nights in Jan 2025
Verified

10/10 Excellent

Arthur P.

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

Great condo

Great location. Quiet but close to everything. Host was very responsive, professional and helpful.
Stayed 7 nights in Oct 2024
Verified

10/10 Excellent

theresa r.

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

Great location

Really enjoyed our stay. Condo has everything you need, including 2 bicycles you can borrow. Owners are very responsive and helpful. I would definitely stay here again.
Stayed 8 nights in May 2024
Verified

10/10 Excellent

Brian I.

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

Great condo in a fantastic location

Fun and well appointed condo in the heart of Key West. Walkable to all the main sights and restaurants. Perfect for a small family without being on top of one another. Excellent communication by owner.
Stayed 7 nights in Feb 2025
Verified

10/10 Excellent

Rudolph S.

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

Wonderful!

Everything was perfect! Beautiful condo in a perfect location.
Stayed 7 nights in Sep 2024
Verified

8/10 Good

Malcolm (Mac) C.

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

Great walkable Key West Location

Just a few blocks from Mallory Square and Duval Street, this is a great condo for seeing all that Key West has by foot. Great pool are to cool off and bike able to the beach. Would definitely recommend!!
Stayed 7 nights in Aug 2024

About the host

Hosted by Jim Bowman

Host profile image
My wife and I purchased our condo after coming to Key West for nearly 20 years. This is our favorite place to escape to. You can truly get on 'island time' here. Whether you are just hanging out on the sundeck or by the pool, biking around the island, or bar hopping, Key West has something to offer everyone. There is really more to do here than most people have the time to do. Our condo has a lot of Key West character . This can be your home away from home also.

We purchased here because Shipyard Condos are located in a private community Truman Annex. We are just two blocks from Duval Street, and do not need a car when we are there. You can just hang out, or be in the heart of everything. Your choice.

We purchased this condo in 2015

Why they chose this property

This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorated. Fresh paint throughout, all new hardwood flooring, new kitchen with granite and stainless steel appliances, and brand new designer furnishings make this a home away from home. A large rear courtyard with a wood sundeck and outdoor grill is perfect for entertaining. Located in the heart of old town Key West, Truman Annex is a gated community of private homes and condominiums. There is an inviting heated swimming pool on premises.

Our home has been featured on the cover of The Key West newspaper because of the 'islandy feel'.

All dining, shopping, and night life are within walking distance from your door. One of the highest-rated national park and beach areas in America is just a short walk away. The Master bedroom has a Queen size bed. 2nd bedroom has 2 single beds. There is a sleeper sofa in the living room. This unit is fully equipped for long, enjoyable stays. All you need is your clothes and toothbrush. Life is good in the Keys! Walk or bike to shopping, dining, fishing, entertainment, beaches, sunsets, Mallory Square, and Duval Street.

What makes this property unique

The large sundeck in the rear courtyard is an extension of the condo, and is lovely almost all months of the year. Nice night lighting and tropical palm trees and plants make for a lush landscape. Great for sunbathing!

Languages:

English

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