Condo

**THE PIRATE’S PENTHOUSE** Condo + Last Key White Glove Service...

Photo gallery for **THE PIRATE’S PENTHOUSE** Condo + Last Key White Glove Service...

A spacious living room with a teal sofa set, a glass coffee table, and a view of the beach through the window.
A house with a porch featuring a statue of a pirate.
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a table set for four.
A coastal town with a prominent yellow house with a wrap-around porch and a grey roof.
A statue of a historical figure on a porch with white railings and a view of a residential area.

Reviews

9.6 out of 10
Exceptional

Highlights

  • Games
    A rare find - enjoy a variety of games available on-site.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Duval Street

Popular amenities

  • Balcony
  • Air-conditioning
  • Refrigerator
  • Washing machine
  • Onsite parking available
  • Non-smoking

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪3 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪5 min walk‬
  • Place, South Beach
    ‪11 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Flamingo Room (Master)

1 King Bed

Guest Bedroom

1 Queen Bed

Living Room

1 Double Sofa Bed

2 bathrooms

First Floor Bath

Second Floor Bath

Spaces

Porch or lanai
Kitchen
Balcony

Add dates for prices

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About the area

Key West

Located by the sea, this condo is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Florida Keys Eco - Discovery Center and Florida Keys National Marine Sanctuary 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 - 3 min walk - 0.3 km
  • Ernest Hemingway Home and Museum - 5 min walk - 0.4 km
  • Fort Zachary Taylor Historic State Park - 10 min walk - 0.9 km
  • South Beach - 11 min walk - 0.9 km
  • Southernmost Point - 12 min walk - 1.1 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 13 min drive

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Blue Heaven - ‬3 min walk
  • ‪Moondog Cafe & Bakery - ‬3 min walk
  • ‪801 Bourbon Bar - ‬3 min walk
  • ‪Mangoes Restaurant - ‬4 min walk

Frequently asked questions

Is **THE PIRATE’S PENTHOUSE** Condo + Last Key White Glove Service... pet-friendly?

No, only service animals are welcome at the property.

How much is parking at **THE PIRATE’S PENTHOUSE** Condo + Last Key White Glove Service...?

On-site parking is available at the property.

What time is check-in at **THE PIRATE’S PENTHOUSE** Condo + Last Key White Glove Service...?

Check-in begins at 4:00 PM.

What time is check-out at **THE PIRATE’S PENTHOUSE** Condo + Last Key White Glove Service...?

Checkout is at 10:00 AM.

Where is **THE PIRATE’S PENTHOUSE** Condo + Last Key White Glove Service... located?

Located in Old Town Key West, this condo building is within a 5-minute walk of Ernest Hemingway Home and Museum and Duval Street. Florida Keys Beaches and Mallory Square are also within 15 minutes.

Reviews

9.6

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. 30 out of 35 reviews
Rating 8 - Good. 4 out of 35 reviews
Rating 6 - Okay. 0 out of 35 reviews
Rating 4 - Poor. 0 out of 35 reviews
Rating 2 - Terrible. 1 out of 35 reviews

9.8/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

9.8/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to relax again from Duvall street but still close
Stayed 3 nights in Jun 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location.
Stayed 4 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful place in the perfect location!
Stayed 5 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and spacious, Perfect location! The property manager was by far one of the best I have ever worked with. We will definitely be booking this location if available again if not will definitely use Last Key Realty, they were amazing!
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

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

Fun week in Key West

Great stay and location!
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location with close proximity and walking distance to everything. Live entertainment downstairs could be enjoyed from the balcony too.
Stayed 4 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a wonderful stay at the Pirate's Penthouse. House was clean, beautiful and every need was well thought out. Host was always available and helpful. Highest recommendation!!!
Stayed 4 nights in Jan 2026
Verified review

10/10 Excellent

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

Great place

Great property, exactly as described. Location was awesome
Stayed 3 nights in Nov 2023
Verified review

10/10 Excellent

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

great location/great place

everything was perfect, you couldn't ask for more- great hosts, always on top of everything, great place, period!!
Stayed 3 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Property conditions & facilities, communication
Beautiful place, very convenient to everything. Duval St is 2 blocks up
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent!
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

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

Great location, spacious and comfortable.

The location has just the right amount of activity and relaxation. The apartment has everything you need with new furniture and appliances. The management staff was very helpful with excursion assistance and helpful suggestions that made our stay special.
Stayed 4 nights in Mar 2025
Verified review

10/10 Excellent

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

Wonderful

Great location. Clean and beautifully decorated
Stayed 3 nights in Dec 2024
Verified review

10/10 Excellent

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

Great place

Great location! Comfortable! Clean! Definitely would visit again.
Stayed 3 nights in Mar 2024
Verified review

10/10 Excellent

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

Pirate stay

I enjoyed everything about it!
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

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

Absolutely fantastic

Pirate's Penthouse was phenomenal! The location was suberb and the interior was clean and modern. My daughter absolutely loved the loft! We would definitely stay there again!
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

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

Amazing location in Key West

Beautiful condo in perfect location for friends weekend. Everything is walkable and some great restaurants and bars very close by. The condo is just as shown in pictures and Last Key rental company is great to work with! Great communication and constant checking made us feel very welcome.
Stayed 5 nights in Jan 2025
Verified review

8/10 Good

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

Great weekend getaway

We loved the location and the space of this unit! It was comfortable and housed everyone perfectly. The only thing I will say is please bring earplugs as it is very noisy at night
Stayed 4 nights in Apr 2024
Verified review

10/10 Excellent

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

We would stay here again!

Fantastic experience, so close to city center we could walk to all areas. Clean, comfortable, and surprisingly quiet in spite of being above and across from a restaurant. That actually made it really fun to sit on the porch and people watch with coffee or cocktails! Bonus - the crepe place below provided a wonderful meal just down our steps. You can hear the roosters, but they are all over the island and they didn't bother me at all. We will stay here again.
Stayed 3 nights in Apr 2025
Verified review

8/10 Good

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

Nice property Wake up with the chickens, literally!

Property was clean and beautifully decorated. There are MANY roosters in this end of Key West, the property would benefit from white noise machines in the bedrooms.
Stayed 4 nights in Mar 2024
Verified review

10/10 Excellent

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

Pirates Paradise

Outstanding experience all around. Very clean and well maintained house. Excellent service from rep. Alena.
Stayed 3 nights in Jan 2024
Verified review

10/10 Excellent

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

Amazing location and manager

The house was perfect, location amazing, and the property manager texted me the whole time and was sooo great!!! She even dropped off cupcakes for my daughters 16th birthday!!! Highly recommend.
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

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

Pirates Penthouse

Our stay at Pirates penthouse was top notch. The space was clean and comfortable and done perfectly. Every little detail was covered. From check in to check out this was in the top shelf experience.
Stayed 4 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Property conditions & facilities, communication
Loved the location, condo was very clean and decorated well. Only issue was the birds roosting above the parking space. Car was covered with bird poo.
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

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

A great stay at the Pirate’s Penthouse

We had an awesome stay at the Pirate’s Penthouse! The unit was exactly as described and exceeded our expectations. It was very spacious and had everything we needed including many extras such as beach towels and chairs that one might not have if flying in. The kitchen was well equipped, although we did not cook much with all of the places in Key West we wanted to go including Blue Heaven across the street. The location was great as it was walking distance to Duval, The Southernmost Point, Hemingway’s House, and more. It was nice to have a parking spot with the unit to load up the car for the beach at Fort Zachary Taylor and further destinations. A great stay!
Stayed 3 nights in Jun 2025
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