See all properties
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

Ahhh - The Pool (heated) With Ocean In Background
View Of Smathers Beach From The Balcony
The captain - watching the ocean for pirates
Living area
Dining Area - Seats 6

Reviews

9.6 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 51350 sq ft

Popular amenities

  • Ocean view
  • Hot tub
  • Kitchen
  • Washer
  • Dryer

Explore the area

View in a 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

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)
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

Ahhh - The Pool (Heated) with Ocean in Background
Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly
  • Ocean view
  • Pool
  • Hot tub
  • Kitchen
9.6 out of 10, Exceptional, (100 reviews)
Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
default

Children

Adults only
default

Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted
Name on credit card must match the name used to make the reservation

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
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

We should mention

A car is recommended for transportation to and from this property

About the neighborhood

Key West

Located on the beach, this condo is in Beachside, a neighborhood in Key West. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and Florida Keys Beaches. 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.
Map
Key West, FL

What's nearby

  • Florida Keys Beaches - 1 min walk - 0.0 km
  • Smathers Beach - 4 min walk - 0.4 km
  • Key West Naval Station - 12 min walk - 1.0 km
  • Clarence S. Higgs Memorial Beach Park - 12 min walk - 1.1 km
  • Duval Street - 8 min drive - 2.3 km

Getting around

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

Restaurants

  • ‪Circle K - ‬14 min walk
  • ‪Starbucks - ‬3 min drive
  • ‪Dions Truman & White - ‬4 min drive
  • ‪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 Mar 21, 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 Jun 1, 2026 start from $509, 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?

Onsite 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?

Check-out 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 2 mi (3 km) of Florida Keys Beaches, Duval Street, and Southernmost Point. Clarence S. Higgs Memorial Beach Park and Key West AIDS Memorial 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. 81 out of 98 reviews
Rating 8 - Good. 14 out of 98 reviews
Rating 6 - Okay. 3 out of 98 reviews
Rating 4 - Poor. 0 out of 98 reviews
Rating 2 - Terrible. 0 out of 98 reviews

10/10

Cleanliness

9.2/10

Check-in

9.6/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jeff M.

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

10/10 Excellent

David V.

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

10/10 Excellent

Lindsey P.

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

10/10 Excellent

Emily B.

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

Great spot for 2 couples

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

10/10 Excellent

robin e.

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

10/10 Excellent

Kelly M.

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

10/10 Excellent

Raymond W.

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

KW Vaca

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

10/10 Excellent

Sally M.

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

10/10 Excellent

molly r.

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

10/10 Excellent

Debbie C.

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

10/10 Excellent

Todd J.

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

10/10 Excellent

Becky H.

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

10/10 Excellent

Deborah S.

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

Great experience!

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

10/10 Excellent

Stephen S.

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

10/10 Excellent

Gina M.

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

10/10 Excellent

Joan B.

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

10/10 Excellent

Diana M.

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

10/10 Excellent

Mark H.

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

10/10 Excellent

George B.

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

8/10 Good

Christopher C.

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

10/10 Excellent

Sharon F.

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

So very NICE

Very nice
Stayed 4 nights in Nov 2019
Verified

10/10 Excellent

Mary B.

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

10/10 Excellent

Coleen M.

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

10/10 Excellent

Rosemary S.

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

No Regrets

Beds are super comfortable, condo is super clean, view is fantastic, easy location to get uber pickup, pool is incredible, complex is very nice secure and clean, Henry is great!!!
Stayed 4 nights in May 2023

About the host

Hosted by Henry Karp

Host profile image

Languages:

English

Premier Host

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

Hotels

Vacation Rentals