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

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On the beach, beach towels
Interior
A swimming pool with a water feature, surrounded by palm trees and lounge chairs.
Outdoor pool, a heated pool
Outdoor pool, a heated pool

Reviews

9.6 out of 10
Exceptional

Entire condo

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.)
    ‪5 min drive‬

Room options

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About the neighborhood

Key West

Located in Beachside within a 5-minute walk of Florida Keys Beaches, this condo is within 2 miles (3 km) of other popular sights like Duval Street. The condo includes a kitchen, a balcony, and a refrigerator.
View more Condo Rentals in Key WestOpens in a new window

What's nearby

  • Florida Keys Beaches - 1 min walk - 0.0 miles
  • Smathers Beach - 4 min walk - 0.3 miles
  • Clarence S. Higgs Memorial Beach Park - 12 min walk - 0.7 miles
  • Key West Naval Station - 13 min walk - 0.7 miles
  • Duval Street - 8 min drive - 1.9 miles

Getting around

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

Restaurants

  • ‪Circle K - ‬14 min walk
  • ‪Dions Truman & White - ‬4 min drive
  • ‪Sandy's Café - ‬3 min drive
  • ‪Starbucks - ‬3 min drive
  • ‪Taco Bell - ‬20 min walk

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)
The condo is air-conditioned and features a kitchen, 2 bathrooms, and a balcony, and there's space to spread out with 2 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a coffee maker, and a phone. Housekeeping is available on request.

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  • Air conditioning
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Total with taxes and fees
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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
  • Kitchenette
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • 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

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
Information provided by the property may be translated using automated translation tools

Rules

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

Pets

  • This property doesn't allow pets

Children and extra beds

  • This property doesn't 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
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.

Property is also known as

Henry's Penthouse on the Ocean in Key West

Frequently asked questions

What is there to do around this condo?

This condo is situated in Beachside, just steps from Florida Keys Beaches. You'll also find Duval Street and Southernmost Point within a short drive.

Will I be able to park at Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals?

Yes, there is a garage.

Is this condo associated with a casino?

No, this condo is not connected to a casino.

Will I find an indoor pool at this condo?

No, this condo doesn't have an indoor pool; however, there are an outdoor pool and a hot tub.

Is Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals a good place to stay for couples?

Amenities that appeal to couples at this beachfront condo include a smart TV and a kitchen in each condo, and some feature ocean view.

Are there hot tubs at Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals?

No, but guests can enjoy a heated pool at this condo.

Does this condo provide breakfast?

No, this condo doesn't offer breakfast.

Will this condo allow pets to stay for free?

No, pets aren't allowed at this condo.

Are there connecting rooms at Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals?

No, there aren't connecting guestrooms at this condo.

How far is the airport from this condo?

The closest major airport to this condo is Key West Intl. Airport (EYW), which is 1.8 mi away (3 minutes by car).

Can I book a room with a balcony at Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals?

Yes, every condo at Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals comes with a balcony and some offer ocean views.

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

Reviews

9.6

Exceptional

Rating 10 - Excellent. 83 out of 100 reviews
Rating 8 - Good. 14 out of 100 reviews
Rating 6 - Okay. 3 out of 100 reviews
Rating 4 - Poor. 0 out of 100 reviews
Rating 2 - Terrible. 0 out of 100 reviews

10/10

Cleanliness

Reviews

Verified

10/10 Excellent

Al D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great condo in a good location. Owner was easy to work with and very responsive. Enjoyed our time in Key West!
Stayed 4 nights in Feb 2026
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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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