Condo

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

Ahhh - The Pool (heated) With Ocean In Background

The captain - watching the ocean for pirates

Overview
Amenities
Policies
Location

Exceptional

2 bedrooms2 bathroomsSleeps 5125.4 sq m

Popular amenities

Hot tub
Dryer
Washer
Free WiFi

Explore the area

Key West, FL

Smathers Beach
‪4 min walk‬
Duval Street
‪4 min drive‬
Southernmost Point
‪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)

Add dates for prices

Amenities

Pool

Hot tub

Kitchen

Washing machine

Dryer

Free WiFi

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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 ecotours and cycling.

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

‪Circle K - ‬14 min walk
‪Starbucks - ‬3 min drive
‪Tin Cup Chalice - ‬11 min walk
‪Salute! On The Beach - ‬14 min walk
‪Sonic Drive-In - ‬18 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?

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 2 mi (3 km) of Florida Keys Beaches, Duval Street and Southernmost Point. Mallory Square and Smathers Beach are also within 3 miles (5 km).

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

Lindsey P.

17 June 2025

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

robin e.

11 Mar 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

Raymond W.

4 Jan 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

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

Sally M.

26 Dec 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

molly r.

21 Sept 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

Kelly M.

9 Mar 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

Todd J.

22 Apr 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

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

Gina M.

6 Nov 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

Stephen S.

15 Feb 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 Feb 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

Sharon F.

30 Nov 2019

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

So very NICE

Very nice

Stayed 4 nights in Nov 2019

10/10 Excellent

Diana M.

25 Feb 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

George B.

12 Apr 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

10/10 Excellent

Mark H.

24 Aug 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

Mary B.

11 May 2025

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

Dawn H.

14 Dec 2022

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

Paradise in the Keys

This was a beautiful large condo!! The location was away from the business but still close enough to enjoy the Duvall crowd if you wanted to The pool and property were top notch. And the neighbors were friendly Henry was a joy to work with. Great communication!

Stayed 5 nights in Dec 2022

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

Coleen M.

29 Apr 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

Audie S.

21 Nov 2022

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

Disliked: Communication

Beautiful

Had a great time…only problem we encountered was no toilet paper when we got there!!

Stayed 5 nights in Nov 2022

10/10 Excellent

Julie N.

14 Dec 2022

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

Great property! Very clean and great communication!

Henry does a great job of communicating. We knew exactly what to do when we got there and also knew what was expected of us. The property was very clean and had everything we needed. This is not beachfront...there is a short walk down the street to get there but it is not too far. We rented a golf cart and took advantage of the parking garage with a convenient spot close to the elevator. The building is dated but the condo was clean and the tropical decor reminded you that you were on vacation. Would stay here again!

Stayed 4 nights in Dec 2022

10/10 Excellent

Debra B.

1 Apr 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

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

About the host

Hosted by Henry Karp

Languages:

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Premier Host

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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

Add dates for prices

Amenities

Have a question?

Similar properties

Key West Beachfront Luxury 2/2 Condo A212

Key West Beachfront Luxury 2/2 Condo A212

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

Lindsey P.

Great Stay Great Location

Lindsey P.

10/10 Excellent

robin e.

Key west weekend

robin e.

10/10 Excellent

Raymond W.

KW Vaca

Raymond W.

10/10 Excellent

Emily B.

Great spot for 2 couples

Emily B.

10/10 Excellent

Sally M.

Perfect!

Sally M.

10/10 Excellent

molly r.

Perfect week in Paradise

molly r.

10/10 Excellent

Kelly M.

Great place!

Kelly M.

10/10 Excellent

Todd J.

Beautiful complex

Todd J.

10/10 Excellent

Debbie C.

Henry's Paradise was paradise!

Debbie C.

10/10 Excellent