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Entire condo

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

Beach condo with a fitness center and a sauna

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

Outdoor pool, a heated pool - Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals (Key West)
Interior - Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals (Key West)
Fridge, microwave, oven, stovetop - Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals (Key West)
Property grounds - Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals (Key West)
On the beach, beach towels - Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals (Key West)
Perched on the top floor, this condo offers spectacular ocean views from its 45 ft private balcony. Relax in style with a wet bar, fully equipped kitchen, and smart TVs in every room. Enjoy Smathers beach just steps away and unwind by the oversized whirlpool or heated pool.

Reviews

9.6 out of 10
Exceptional

Entire condo

2 bedrooms2 bathroomsSleeps 51350 sq ft

Popular amenities

  • Hot Tub
  • Dryer
  • Washer
  • Kitchen

Add dates for prices

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

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)

Property amenities

Beach

  • On the beach
  • Beach towels

Pool/Spa

  • Communal pool
  • Heated pool
  • Hot tub
  • Outdoor pool
  • Sauna

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Car recommended
  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Books
  • Smart TV with cable/satellite channels
  • Stereo

Outdoor areas

  • Balcony
  • Barbecue grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Elevator
  • Smoking not allowed

Services and conveniences

  • Housekeeping (on request)
  • Iron/ironing board
  • Phone

Location highlights

  • Near the marina
  • Near the ocean

Things to do

  • Gym
  • Heated pool
  • Tennis
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water skiing nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Housekeeping (on request)
  • Property does not allow children
  • Unit size: 1,350 square feet

Similar properties

Outdoor pool, a heated pool

Key West Beachfront Luxury 2/2 Condo A212

  • Pool
  • Hot Tub
  • Kitchen
  • Washer
10.0 out of 10, Exceptional, 158 reviews
Key West Beachfront Luxury 2/2 Condo A212

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Rules

Name on credit card must match the name used to make the reservation

Pets

Pets not allowed

Children and extra beds

This property does not allow children

Events

No events allowed

Smoking

Smoking is not permitted

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

A car is recommended for transportation to and from this property

Property is also known as

Henry's Penthouse on the Ocean in Key West

About the neighborhood

Map
Key West, FL

What's nearby

  • Smathers Beach - 4 min walk - 0.3 miles
  • Clarence S. Higgs Memorial Beach Park - 12 min walk - 0.7 miles
  • Duval Street - 4 min drive - 1.3 miles
  • Southernmost Point - 4 min drive - 1.3 miles
  • South Beach - 4 min drive - 1.3 miles

Getting around

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

Restaurants

  • ‪Circle K - ‬14 min walk
  • ‪Tin Cup Chalice - ‬11 min walk
  • ‪Starbucks - ‬3 min drive
  • ‪Sonic Drive-In - ‬18 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.

Is Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals pet-friendly?

No, pets are not allowed at this 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. Mallory Square and Smathers Beach are also within 3 mi (5 km).

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

Reviews

9.6

Exceptional

Rating 10 - Excellent. 80 out of 97 reviews
Rating 8 - Good. 14 out of 97 reviews
Rating 6 - Okay. 3 out of 97 reviews
Rating 4 - Poor. 0 out of 97 reviews
Rating 2 - Terrible. 0 out of 97 reviews

10/10

Cleanliness

Reviews

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

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

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

10/10 Excellent

Sharon F.

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

So very NICE

Very nice
Stayed 4 nights in Nov 2019

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

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

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

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

10/10 Excellent

Debra B.

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

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

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

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

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

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

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

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

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

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

10/10 Excellent

Susan B.

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

Pink palace

The property was great, albeit very pink. I didn’t know there were so many shades of pink or that there were so many different things that were pink! The property is further away from the activities that we did, but it was near two beaches and it was relatively quiet. All in all, we had a great weekend. We used the pool and walked along the beach. We visited several places on duval street. Key West is very easy to navigate on foot, by motorbike, golf cart, or car. We didn’t spend a lot of time in the condo, but the beds were very comfortable. We enjoyed having our morning coffee on the patio, and we did spend a few hours at the pool. We rented a golf cart for the weekend and the parking spot was super convenient to the elevator. I would recommend this property to friends.
Stayed 2 nights in Jun 2023

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

10/10 Excellent

Eliot O.

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

Nice Place to Stay

Property was exactly as advertised, although the view of the beach was somewhat tangential. Having a reserved parking spot in the garage right next to the elevator was very convenient. The location wasn't really in walking distance of anything of interest, but nothing was more than 10 minutes away by car. The apartment itself was well-furnished and everything worked as it should. The only warning is that the second bedroom is separated from the living room by a wall that doesn't go all the way to the ceiling, so some level of privacy might be compromised, although it wasn't an issue for us. We'd certainly consider staying here again when we come back to Key West.
Stayed 6 nights in May 2023

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

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

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

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