Entire 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 beach with white lounge chairs, a palm tree, and a clear blue sky. - Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals (Key West)
A swimming pool with a hot tub, surrounded by palm trees and lounge chairs. - Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals (Key West)
A spacious indoor area with a high ceiling, large windows, and a dining area with wicker furniture. - Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals (Key West)
A gym with various exercise equipment, large windows, and a view of greenery. - Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals (Key West)
An aerial view of a tennis court surrounded by lush greenery and residential buildings. - Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals (Key West)
Near Smathers Beach, Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals provides laundry facilities, a gym and a sauna. For some rest and relaxation, visit the hot tub. Guests can connect to free in-room WiFi.

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Ocean view
  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer

Add dates for prices

About this property

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

  • Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back year after year. If the dates you need are not available check my other Key West vacation rental (Henry's Piece Of Paradise) located in the same 1800 Atlantic complex.

    Both these Key West vacation rental properties were decorated and are managed (and maintained) by me personally, assuring you of a memorable vacation in a property that is way above the average
    investor owned rentals offered by management companys.

    Make your reservations now - I easy to reach and easy to talk to.



    Inside:

    . View the Atlantic ocean while laying in bed.
    . King in master, King in 2nd bedroom (yes, 2 king beds) and A full size
    sleeper sofa in the living room.
    . Fully equipped kitchen with dishwasher, microwave, full
    size range, ice maker.
    . Full size washer and dryer in the unit.
    . Wet bar.
    . Internet smart TV's with TV sets in living, guest and master
    bedroom.
    . Sonos WIFI speakers in the living room, both bedrooms and the kitchen
    . Private phone
    . Available housekeeping.
    . Smoke and pet free.



    Outside:

    Ahhh the weather, The average temperature is 77.8 degrees, making Key West the warmest city (average temperature) in the United States. It has never been below 41 or above 98 degrees. Ahhh paradise.

    . Just steps to Smathers beach, the largest public beach
    in Key West.
    . Olympic size heated pool. (35'x 70'x 9' deep)
    . Over Size whirlpool adjacent to the swimming pool.
    . 400 ft. of private ocean footage.
    . 3 lighted tennis counts (1 is clay)
    . BBQ with picnic huts.
    . 24 hr. security.
    . Covered / secured parking.
    . Clubhouse is available for special events such as
    weddings.






    Activities and attractions

    . 1 mile = Famous Duval St. Dining, dancing, live entertainment, partying, shopping, arts or whatever.
    . 1 mile = Key West airport.
    . 0--2 miles = Scuba diving, snorkeling , sailing, jet skiing, parasailing, boat / kayak rentals, deep sea fishing -
    every water sport you can imagine.
    . 0--2 miles = Sunset / starlight cruses.
    . 2 miles = 18 hole champion golf course.
    . 1--2 miles = moped or bicycle rentals.
    . 1--2 miles = airplane / seaplane tours.
    . 0-- miles = lazing away the entire day. (it's perfectly respectable here in Key West)

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About the area

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 cycling and ecotours. Visit our Key West travel guide
View more Condo rentals in Key West
Map
Key West, FL

What's nearby

  • A wooden signpost with city names and distances, a beach with umbrellas, and lounge chairs.
    Florida Keys Beaches
    1 min walk - 0.0 km
  • A beach with white sand, palm trees, and a building in the background.
    Smathers Beach
    4 min walk - 0.4 km
  • A beach sign with rules and hours for Clarence S. Hughes Memorial Beach.
    Clarence S. Higgs Memorial Beach Park
    12 min walk - 1.1 km
  • A military jet flying low over a concrete path surrounded by vegetation.
    Key West Naval Station
    13 min walk - 1.2 km
  • A street with a pharmacy, a theater, and a yellow building.
    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
  • Circle K
    14 min walk
  • Starbucks
    3 min drive
  • Taco Bell
    20 min walk
  • Tin Cup Chalice
    11 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.

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).

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Reviews

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

9.6

Exceptional

10

Cleanliness

9.6

Location
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

Reviews

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, 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

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

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

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

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
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

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

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
Verified review

10/10 Excellent

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

Great condo

Enjoyed our stay, large condo, exceptionally large deck and very clean. Only glitch is that upon checking in the directions are not exactly clear. You check in by talking with security through a speaker inside one end of the building and then need to go to another speaker at the other end of the building to get directions as to where to drop off the sign-in sheet. There is no signage as to the building number, but the address is clear, just need to know east and west ends of the building, again not marked. Otherwise, our 5 nights were wonderful and we enjoyed being near the beach, away from the downtown congestion and appreciated the security of a parking garage. Henry was also very responsive to questions.
Stayed 5 nights in May 2025
Verified review

10/10 Excellent

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

Key West Pink

If you like the color pink - this is your place! It was definitely a Key West vibe in this condo. Henry was awesome and gave us ideas and advice on where to go and what to do! We were there with another couple from our family. The condo was well appointed with many extras for the beach and pool that we were able to use. There were enough appliances, utensils, etc. in the kitchen.We loved the pool and beach area around the condo building. The sunrises were spectacular!It was a little far from downtown, but manageable for a long walk, drive, or uber/lyft. Unfortunately, there was a lot of construction on our road during our stay - so that was noisy. Also, it is a bummer for the couple that are in the second bedroom because the wall does not go all the way to the ceiling. So if they wanted to go to bed earlier, we had to lower all of the lights and the volume of the TV so as not to bother them. One other item that could be taken down are some of the mirrors - yikes!
Stayed 5 nights in Mar 2025
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

Henri's Slice of Paradise

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

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

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

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
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

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