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Rooftop Penthouse

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Interior - Rooftop Penthouse (Key West)
Interior - Rooftop Penthouse (Key West)
2 bedrooms, blackout drapes, iron/ironing board, free WiFi - Rooftop Penthouse (Key West)
Fridge, microwave, oven, stovetop - Rooftop Penthouse (Key West)
Smart TV - Rooftop Penthouse (Key West)
Key West's vibrant Duval Street is at your doorstep in the Rooftop Penthouse. Unwind with a drink on your private rooftop terrace, taking in the views of Duval Street from above. The spacious living room features high ceilings and plenty of natural light, while a fully equipped chef kitchen makes entertaining easy.

Reviews

10 out of 10
Exceptional

Entire condo

2 bedrooms2 bathroomsSleeps 61800 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

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.

Rooftop Penthouse

Summary:

Rooftop Penthouse- Luxury Penthouse in prime Downtown location



The Space:

The high-end sophisticated Rooftop Penthouse is located directly above the famous Wyland Gallery on Duval Street. Enjoy Dining, Shopping, and Entertainment in the heart of Key West. Once you enter the property through your private entrance, you would be captivated by its expansive space. The oversized living room with a high 15 FT ceiling has an abundance of natural light coming from the French doors and floor to ceiling windows. Florida is all about outdoor living; we have the pleasure to offer you a private rooftop terrace where you can enjoy the dazzling view of Duval street from the front row seat. Open your living room with french doors and combine the indoor and outdoor spaces. There’s nothing better than feeling like you’re on top of the world.



Open floor plan living room has comfortable couches and a flat-screen Tv to help relax after all day sightseeing and shopping.



For those who love to entertain and cook, we offer a fully equipped chef kitchen with new stainless steel appliances, granite countertops, and dark wood cabinets.



Master Bedroom has a King bed and comfortable seating area, couch can convert into queen sleeper sofa nad can sleep additional 2 guests. Plush towels and high-end linens are available for the most discerning guests. The second bedroom is open to a living room, has a King size bed, and can be closed off ONLY with blackout curtains. There are no walls.



The great news is that your furry friends are all welcome to enjoy Key West with you.  A newly constructed park, " Truman  Waterfront," is just 10 min walk away as well as the most beautiful beach and a state park Ft. Zachary Taylor.



Rooftop Penthouse features>>

- Two bedrooms with king beds

- 1 full bathroom with stand up shower

- 0.5 powder room accessible from Outdoor terrace only, no AC

- Laundry/utility room with powder room

- Rooftop private entertaining terrace

- One free off Street parking behind the building



Washer & Dryer >> Central Heat and A/C >> Ceiling Fans >> Flat Screen TVs in Living Room & Master Bedroom>> Fully Equipped Kitchen>  Starter supply of paper products >> Starter set of cleaning products >> Linens and Towels provided >> Wireless high-speed Internet access & full cable included

Interim housekeeping provided upon request >> This property will accommodate up to 6 adults >> No Pets

Property amenities

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Free offsite parking
  • Onsite parking options include a garage

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1.5 bathrooms
  • Bathtub
  • Hair dryer
  • Shampoo
  • Shower

Living spaces

  • Dining table

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Rooftop terrace

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Blackout drapes
  • Iron/ironing board

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Unit size: 1,800 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in available

Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

Guests can access their accommodation through a private entrance

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

Thank You for choosing Keys Vacation Rentals for your vacation rental accommodation. You will be contacted by one of our property managers within 2...

Access methods

Private entrance

Pets

Pets not allowed

Children and extra beds

Children are welcome

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 indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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

Frequently asked questions

Is Rooftop Penthouse pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Rooftop Penthouse?

As of May 22, 2026, prices found for a 1-night stay for 2 adults at Rooftop Penthouse on May 25, 2026 start from $960, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

There is free parking nearby.

What time is check-in at Rooftop Penthouse?

Check-in begins at 4:00 PM.

What time is check-out at Rooftop Penthouse?

Check-out is at 10:00 AM.

Where is Rooftop Penthouse located?

Located in Old Town Key West, this condo building is steps from San Carlos Institute - Casa Cuba and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 15 minutes.

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Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 49 out of 54 reviews
Rating 8 - Good. 5 out of 54 reviews
Rating 6 - Okay. 0 out of 54 reviews
Rating 4 - Poor. 0 out of 54 reviews
Rating 2 - Terrible. 0 out of 54 reviews

9.8

Cleanliness

10

Location

9.0

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Courtney L.

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

Great VRBO!

This is an amazing property in an amazing location.
Stayed 4 nights in Nov 2024
Verified

10/10 Excellent

Katherine R.

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

Great Place 2nd Stay @ property

2nd time we’ve stayed here, Great comfy beds & pillows, great location & patio, giant lounge-able couch, we’ll be back
Stayed 5 nights in Jan 2024
Verified

10/10 Excellent

Mitchell S.

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

Great location

We loved the condo. Great location. Wonderful outdoor deck overlooking Duval st. Would definitely stay there again.
Stayed 3 nights in Jan 2025
Verified

10/10 Excellent

Diana R.

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

Best Location!

Totally enjoyed our stay here. Great location. The outside patio is incredible. Highly recommend
Stayed 4 nights in Jan 2025
Verified

10/10 Excellent

Julie M.

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

Key West

Perfect location and lots of space!
Stayed 2 nights in Mar 2025
Verified

10/10 Excellent

Betsy M.

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

Terrific

It was a great location, nice property and fun time!
Stayed 3 nights in Nov 2024
Verified

10/10 Excellent

Hillary R.

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

Great luxury apartment

Beautiful apartment in a great location
Stayed 2 nights in Jul 2024
Verified

10/10 Excellent

kristen g.

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

AWESOME

This was the best place to stay for fantasy fest!! Ideal location, extremely clean and plenty of room!!
Stayed 3 nights in Oct 2024
Verified

10/10 Excellent

Christine V.

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

Friends Quick vacay

Excellent location to use as home base to explore Key West. The amenities were as advertised. We enjoyed being able to sit on the balcony and have drinks while people watching.
Stayed 2 nights in Mar 2024
Verified

10/10 Excellent

connie f.

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

Fun in the Keys

The apt was awesome. We were smack dab in the middle of everything. It was also very clean.
Stayed 2 nights in Jan 2025
Verified

10/10 Excellent

Jeff D.

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

Great stay in Key West

The property was great. Spacious with everything you need. We especially liked the patio. We spent a great deal of time people watching from the deck. It was centrally located, close to bars, restaurants and attractions. Would highly recommend. Access was simple as well.
Stayed 3 nights in Feb 2025
Verified

10/10 Excellent

erin m.

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

Great place on Duval

We booked this condo for the powerboat races and we’re not disappointed. The accommodations were exactly as described, the kitchen was well appointed and the view/people watching can not be beat! There’s plenty of room to have some friends over for drinks on the patio, or just relax on the loungers and get some sun.
Stayed 6 nights in Nov 2024
Verified

8/10 Good

Kim

Liked: Cleanliness, amenities, property conditions & facilities
The location is excellent. The decor was very nice. Would’ve been easier to be able to get in the back door for loading and unloading the remotes needed new batteries overall I give it a 9
Stayed 2 nights in Jan 2024
Verified

10/10 Excellent

Kelly

Liked: Cleanliness, amenities, property conditions & facilities, communication
Spacious. Comfortable. Rooftop area especially unique for Duval Street gazing.
Stayed 3 nights in Dec 2023
Verified

10/10 Excellent

Andrea S.

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

Girlfriends Key West Getaway

It’s hard to find a place that can sleep 3 adults in separate beds but this apartment fit the bill with the pull out sofa options. Apartment is modern & stylish, chilling on the roof deck overlooking Duval street is fun. Plenty of space to spread out & super clean.
Stayed 1 night in Mar 2024
Verified

10/10 Excellent

Rick M.

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

Great Location with a great feel

Loved the location and ease of getting everywhere we needed downtown! Everything on the inside was very clean and more upscale than several VBROs we have stayed at. The only thing that would have helped is in the instructions mention that you can easily walk down the alley to the right as walk out the front door (near the Italian/pizza place). Walked down the block to the left twice before I realized there was a quicker way.
Stayed 2 nights in Mar 2025
Verified

10/10 Excellent

Rob D.

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

HD

If you like to people watch the location was amazing! Located right on Duval in the middle of everything. We couldn’t get over how clean it was. The kitchen had everything you could possibly ever need. To top it all off was how incredible the property manager was. Thank you Hana!
Stayed 4 nights in Sep 2024
Verified

10/10 Excellent

Lisa E.

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

Great location

Perfect location and the entrance is on Duval street too. Balcony was nice to have especially in the mornings. Note that the 1/2 bath is off the balcony and not inside. From the photos looked like the full bath was inside the master suite, but it's in the hall so you don't have to disturb whoever is in the bedroom.2nd bed is curtained off in the mail living space, but is a dresser and night stand so worked great.
Stayed 2 nights in Jan 2025
Verified

10/10 Excellent

Melanie S.

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

Perfect spot

We had one night in Key West. This was perfect location. Just right amount of space for five adults. Another full bath would have probably been ideal but what was there met our needs. Very clean. Good communication. Easy to get in and out. Nice parking space. Would recommend.
Stayed 1 night in Dec 2023
Verified

10/10 Excellent

Abigail Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a great stay! Great location house was clean and had several things for us to use!
Stayed 3 nights in Nov 2025
Verified

10/10 Excellent

Libby S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
wonderful place!!
Stayed 1 night in Jul 2025
Verified

10/10 Excellent

Jonny D.

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

Great Place, Great Location

Really enjoyed this place and it is right off of Duval!
Stayed 3 nights in Aug 2024
Verified

10/10 Excellent

kelley b.

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

Great location

Had a great time with family
Stayed 2 nights in Nov 2023
Verified

10/10 Excellent

Steven K.

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

Wow, what an amazing place!

100% I would stay here again. Great location, easy check in process, and everything from the decor to the comfortable bed beds was amazing. Highly recommended.
Stayed 2 nights in Jun 2025
Verified

10/10 Excellent

Susan D.

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

Excellent

We really enjoyed our stay here. Great location, huge private deck to hang out on, clean, light and airy space. Nicely eqipped kitchen. We would definitely stay again!!
Stayed 3 nights in May 2025