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

See all properties

Condo

Ahhh - The Pool (heated) With Ocean In Background

The captain - watching the ocean for pirates

Overview
Amenities
Policies
Location
Host

Exceptional

2 bedrooms2 bathroomsSleeps 5125.4 sq m

Popular amenities

Hot tub
Dryer
Washer
Air conditioning

Explore the area

Key West, FL

Smathers Beach
‪4 min walk‬
Clarence S. Higgs Memorial Beach Park
‪12 min walk‬
Duval Street
‪4 min drive‬
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

Balcony

Dining area

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)

Property manager

Henry Karp

Premier Host

Languages

English

Add dates for prices

Amenities

Pool

Hot tub

Kitchen

Washer

Dryer

Free WiFi

Have a question?

Beta

Get instant answers with AI powered search of property information and reviews.

Ask a question

Similar properties

Hot Tub by the Sea, Overlooking the Pool and Atlantic

Ocean view
Pool
Hot tub
Kitchen

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 11:00 AM

Children

Adults only

Events

No events allowed

Pets

No pets allowed

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

On-site 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 transport to and from this property

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 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.

Key West, FL

What's nearby

Smathers Beach - 4 min walk - 0.4 km
Clarence S. Higgs Memorial Beach Park - 12 min walk - 1.1 km
Duval Street - 4 min drive - 2.0 km
Southernmost Point - 4 min drive - 2.0 km
South Beach - 4 min drive - 2.0 km

Getting around

Key West, FL (EYW-Key West Intl.) - 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?

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 3 mi (5 km) of Florida Keys Beaches, Duval Street and Mallory Square. Smathers Beach is 3.1 mi (4.9 km) away.

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

9.2/10

Check-in

9.6/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

10/10 Excellent

Jeff M.

30 April 2025

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.

22 April 2025

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

robin e.

11 March 2025

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.

25 February 2025

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

Raymond W.

4 January 2025

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

KW Vaca

Great location. Close to everything

Stayed 5 nights in Dec 2024

10/10 Excellent

Sally M.

26 December 2024

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

Debra B.

1 April 2025

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

Gina M.

6 November 2024

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

molly r.

21 September 2024

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

Emily B.

15 June 2024

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

Debbie C.

29 June 2024

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

Kelly M.

9 March 2024

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

Stephen S.

15 February 2024

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.

12 June 2023

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

Deborah S.

12 February 2023

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

Mark H.

24 August 2023

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

Joan B., Bellbrook

17 February 2021

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

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

10/10 Excellent

3 June 2010

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.

12 April 2023

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

8/10 Good

Christopher C.

7 November 2018

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

10/10 Excellent

Coleen M.

29 April 2023

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.

5 May 2023

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.

31 May 2023

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.

19 June 2023

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.

2 August 2020

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

About the host

Hosted by Henry Karp

Languages:

English

Premier Host

They consistently provide great experiences for their guests

Tell us how we can improve our siteShare feedback

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

Reviews

Popular amenities

Explore the area

Rooms & beds

2 bedrooms (sleeps 5)

Guest

Master

2 bathrooms

2nd Bathroom

Master Bath - In suite

Spaces

About this property

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

Property manager

Languages

Add dates for prices

Amenities

Have a question?

Similar properties

Key West Beachside Spacious Two Bedroom Condo in the Top Location on the Key

Key West Beachside Spacious Two Bedroom Condo in the Top Location on the Key

House Rules

Children

Events

Pets

Smoking

Important information

You need to know

We should mention

About the area

Key West

What's nearby

Getting around

Restaurants

Frequently asked questions

Reviews

Exceptional

10/10

9.2/10

9.6/10

9.6/10

9.8/10

Reviews

10/10 Excellent

Jeff M.

Henri's Slice of Paradise

Jeff M.

10/10 Excellent

Todd J.

Beautiful complex

Todd J.

10/10 Excellent

robin e.

Key west weekend

robin e.

10/10 Excellent

Diana M.

Family getaway!!

Diana M.

10/10 Excellent

Raymond W.

KW Vaca

Raymond W.

10/10 Excellent

Sally M.

Perfect!

Sally M.

10/10 Excellent

Debra B.

Key West Pink

Debra B.

10/10 Excellent

Gina M.

Excellent

Gina M.

10/10 Excellent

molly r.

Perfect week in Paradise