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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

Outdoor pool, a heated pool
Interior
Property grounds
On the beach, beach towels
2 bedrooms, iron/ironing board, free WiFi, bed sheets

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 manager

Henry Karp

Languages

English

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

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, 97 reviews
Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly

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

Pets

Pets not allowed

Children and extra beds

This property does not allow children

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

  • ‪Starbucks - ‬3 min drive
  • ‪Salute! On The Beach - ‬15 min walk
  • ‪Sandy's Cafe - ‬3 min drive
  • ‪Taco Bell - ‬19 min walk
  • ‪El Siboney Restaurant - ‬4 min drive

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. Clarence S. Higgs Memorial Beach Park and Key West AIDS Memorial are also within 15 minutes.

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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

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

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

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

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

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

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

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

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

Deborah S.

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

Great experience!

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

10/10 Excellent

Joan B., Bellbrook

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

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
This review was submitted before 2018 and has not been verified.

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!

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

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

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

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

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

Kelly H.

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

Beautiful Condo In Paradise

We had decided on an impromptu beach vacation for this summer and felt we had to act fast. We usually rent a condo at another US beach destination but it wasn't available. We've had great success using this site for a weekend trip in the mountains so decided to give it a go to visit Key West. When we vacation every summer we stay at the same high end condo at the beach. We've also traveled to Mexico and the Caribbean and stay at high end resorts. Due to this being so last minute and under current circumstances, we lowered our expectations and simply hoped for the best. When we arrived the check in process was quick and easy. The owner provided specific instructions to follow. We entered the condo and we all smiled and were amazed at how beautiful it was! It was absolutely spotless. The condo is incredibly spacious with a large kitchen and open space dining room/living room. The bedrooms and bathrooms are also very roomy. The condo as a very long balcony that starts from the living room and extends to the master bedroom. Each room has its own sliding door. The balcony is spacious and beautiful with a nice view. The decor of the space is whimsical and fun and captures the heart of Key West! There are special touches everywhere you look. The property has a very large and beautiful pool with a stunning view of the ocean. The pool deck and chairs were clean and in excellent condition. We don't play tennis but the courts looked really nice as well. It's a very short and easy 5 min. walk to Smathers Beach where there are water sport rentals available. It's not great for snorkeling, but we had our own mask and snorkel set just for kicks and we did see a few small and colorful fish. The beach is clean and beautiful. The location is a bit out from Duval and Mallory Square. We were fine with that as we prefer things quiet at night. It was a very quick and easy drive to both for dining and going out at night. Parking was easy due to not as many people this year. I'm sure under normal circumstances it's not best to drive to Duval or Mallory. There are MANY places that rent small scooters and little electric cars to get around and I'd highly recommend that if KW is busy. The residents of the property that we chatted with by the pool were all very friendly. We had a very enjoyable and relaxing trip and stay. I highly recommend this condo for couples or small families. It's perfect.
Stayed 7 nights in Jul 2020

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

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

Lori K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Dec 2024

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

Izabela G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 8 nights in Aug 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

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

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