Condo

Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals

Photo gallery for Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals

A pool area with blue umbrellas, lounge chairs, and palm trees.
A balcony with a view of the ocean and palm trees.
A room with a large window, a sofa, a painting, and a statue of a pirate with a parrot.
A living room with a large window, a sofa, a coffee table, and a person in a pirate costume.
A modern kitchen with a glass dining table, colorful chairs, and a stone accent wall.

Reviews

9.6 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • On the beach
    A rare beachfront property in the area - enjoy direct access to the beach and sea.
  • Discover nearby landmarks
    Close to Florida Keys Beaches

Popular amenities

  • On beach
  • Balcony
  • Spa pool on site
  • Outdoor pool
  • Kitchenette
  • On-site fitness centre

Explore the area

View map
Key West, FL
  • Place, Florida Keys Beaches
    ‪1 min walk‬
  • Place, Smathers Beach
    ‪4 min walk‬
  • Place, Clarence S. Higgs Memorial Beach Park
    ‪12 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪4 min drive‬

Rooms & beds

2 bedrooms (sleeps 5)

Guest

1 King Bed

Master

1 King Bed

2 bathrooms

2nd Bathroom

Master Bath - In suite

Spaces

Deck or patio
Kitchen
Kitchenette
Balcony
Dining area

Add dates for prices

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Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly
Beachside
  • Ocean view
  • Pool
  • Spa pool
  • Kitchen
9.6 out of 10, Exceptional, (106 reviews)
Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly

About the area

Key West

Located on the beach, this condo is in Beachside, a neighbourhood in Key West. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Key West Butterfly and Nature Conservatory and Sails To Rails Museum at Flagler Station are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with ecotours and cycling.
Map
Key West, FL

What's nearby

  • Florida Keys Beaches - 1 min walk - 0.0 km
  • Smathers Beach - 4 min walk - 0.4 km
  • Clarence S. Higgs Memorial Beach Park - 12 min walk - 1.1 km
  • Key West Naval Station - 13 min walk - 1.2 km
  • Duval Street - 5 min drive - 2.0 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 3 min drive

Restaurants

  • ‪Denny's - ‬4 min drive
  • ‪Starbucks - ‬3 min drive
  • ‪Circle K - ‬14 min walk
  • ‪Tin Cup Chalice - ‬11 min walk
  • ‪Taco Bell - ‬20 min walk

Frequently asked questions

Does Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals have a pool?

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

How much does it cost to stay at Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals?

As of 15 Nov 2026, prices found for a 1-night stay for 2 adults at Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals on 20 Nov 2026 start from AU$4,148, 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 Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals pet-friendly?

No, pets are not allowed at this property.

How much is parking at Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals?

On-site parking is available at the property.

What time is check-in at Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals?

Check-in begins at 4:00 PM.

What time is check-out at Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals?

Checkout is at 11:00 AM.

Where is Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals located?

Nestled on the beach, this Beachside condo building is within 1 mi (2 km) of Clarence S. Higgs Memorial Beach Park and Florida Keys Beaches. Duval Street and Southernmost Point are also within 2 miles (3 km).

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. 83 out of 100 reviews
Rating 8 - Good. 14 out of 100 reviews
Rating 6 - Okay. 3 out of 100 reviews
Rating 4 - Poor. 0 out of 100 reviews
Rating 2 - Terrible. 0 out of 100 reviews

10/10

Cleanliness

9.2/10

Check-in

9.6/10

Communication

9.6/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a delightful, just perfect way to start a visit to Key West. The condo was a perfect reflectionOf the colors of life in Key West. IT took us 2 days to absorb all the exquisite details. Parking easy, pool areas large with adequate lounge space and umbrellas for sun protection. A very short walk to Smithers Beach where beach rentals are available. Had a great time
Stayed 7 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great condo in a good location. Owner was easy to work with and very responsive. Enjoyed our time in Key West!
Stayed 4 nights in Feb 2026
Verified review

10/10 Excellent

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

Great spot for 2 couples

Great location; excellent pool.
Stayed 4 nights in May 2024
Verified review

10/10 Excellent

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

Beautiful property in a great location

Centrally located and convenient to all of the popular Key West attractions and beaches. Property was clean and well maintained.
Stayed 4 nights in Mar 2025
Verified review

10/10 Excellent

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

Henri's Slice of Paradise

Terrific Condo in a great location.
Stayed 5 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, communication, location, listing accuracy

Great place!

Caribbean themed accommodation that is absolutely perfect! Tons of room and the decor is delightful.
Stayed 5 nights in Mar 2024
Verified review

10/10 Excellent

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

Key west weekend

We had a lovely stay. The heated outdoor pool was a delight. The condo was spacious and clean. We had excellent meals, salute restaurant on highs beach, blue heaven and Grignote bakery.
Stayed 3 nights in Mar 2025
Verified review

10/10 Excellent

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

Perfect week in Paradise

Great location, great apartment, great pool. Host was great at communicating. Would love to go back!
Stayed 7 nights in Sep 2024
Verified review

10/10 Excellent

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

Clean and Festive!

Condo was as listed, very clean,safe and Festive. Would stay again.
Stayed 5 nights in Jun 2023
Verified review

10/10 Excellent

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

Henry's Paradise was paradise!

The place was beautiful with a great view. The pool was very large and very clean. We had everything we needed with shopping close by. It was a very nice vacation!
Stayed 4 nights in Jun 2024
Verified review

10/10 Excellent

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

Great experience!

Beautiful property and very well kept
Stayed 2 nights in Feb 2023
Verified review

10/10 Excellent

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

KW Vaca

Great location. Close to everything
Stayed 5 nights in Dec 2024
Verified review

10/10 Excellent

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

Great Stay Great Location

We had a great stay at Henry's Penthouse. The condo was large and welcoming. The property is beautiful and has a great pool and beach area. Two minor issues were resolved quickly and Henry is very responsive. Would definitely return. Thanks Henry!
Stayed 4 nights in Jun 2025
Verified review

10/10 Excellent

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

Beautiful Keys

Great location. Beautiful few of the ocean from the balcony. Nice covered parking and a short drive to downtown.
Stayed 4 nights in Feb 2024
Verified review

10/10 Excellent

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

Great accommodations

We really enjoyed this spacious condo. The large balcony was very comfortable and spent most evenings enjoying the fresh air. I love to cook and appreciated the well stocked kitchen.
Stayed 7 nights in Feb 2021
Verified review

10/10 Excellent

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

Perfect!

Beautiful condo completely equipped for a week long family vacation. Location was good. Amenities—pool, hot tub, racquetball—well maintained. Plenty of fun activities within walking distance.
Stayed 7 nights in Dec 2024
Verified review

10/10 Excellent

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

Great place and good security

The condo was spacious. Well furnished. What I thought was great was the long balcony that each bedroom had access to. Was nice to sit out there at night with the sea breeze blowing and visit with good friends.
Stayed 6 nights in Aug 2023
Archival

10/10 Excellent

We had a fabulous time st...

We had a fabulous time staying in Key West and a great time at the condo. The location was ideal for our family, close to the beach, but in a quiet section of the island. The master bathroom was fantastic! The views from the balcony were exactly what we came to Key West to see!
Verified review

10/10 Excellent

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

Excellent

Henry’s penthouse was very nice and very clean. It was well equipped with everything that we needed in order to be comfortable. The location was also very good. Henry is super responsive. We will definitely stay here again whenever we return to Key West.
Stayed 7 nights in Oct 2024
Verified review

8/10 Good

Pleasant Condo

Very nice place with all the things you need to enjoy your brief moments indoors while in Key West. The location is not accessible to downtown on foot but you can uber or drive in fine.
Stayed 4 nights in Oct 2018
Verified review

10/10 Excellent

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

Relaxing

Great location … close to all the action yet far enough away! Henry was great with communication. The property was great! We will be back!
Stayed 5 nights in Apr 2023
Verified review

10/10 Excellent

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

So very NICE

Very nice
Stayed 4 nights in Nov 2019
Verified review

10/10 Excellent

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

Beautiful complex

It is true what is said about this unit. If you like pink. Then this is the place to be. The complex was great. Nice pool, no fighting for chairs and clean. Wish the sliders had screens to get some fresh air. Unit was cleaned and Henry is very responsive.
Stayed 7 nights in Apr 2025
Verified review

10/10 Excellent

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

Very comfortable and spacious

We spent a week with another couple at Henry’s Penthouse and had a great time. The location is great for beach activities, although due to the sargassum issue the ocean wasn’t really accessible. The kitchen is really big and equipped to cook full meals if you want to. The living area is very comfortable. The unit worked well for two couples.
Stayed 7 nights in Apr 2023
Verified review

10/10 Excellent

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

Family getaway!!

Rented Henry’s Penthouse for a getaway with son and daughter in law. Was wonderful to have the 2 full bathrooms and 2 king bedrooms. The kitchen was probably the best stocked of any VRBO I have rented (and there have been many). Henry was kind enough to check in with us to make sure all was well with us and offer his assistance as needed. We never needed any extra help since everything was pretty much perfect. If we ever get back to Key West we will stay here again!! Thanks Henry!!
Stayed 10 nights in Feb 2025
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