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Rooftop Penthouse

Condo near Duval Street in Key West

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Photo gallery for Rooftop Penthouse

A modern living room with a glass dining table, grey chairs, and a white sofa.
A spacious room with a white sofa, a TV, and a view of the outdoors through large windows.
A modern living room with a sofa, a round coffee table, a side table, and a painting on the wall.
A kitchen with granite countertops, stainless steel appliances, dark wooden cabinets, and a window overlooking greenery.
A modern bedroom with a bed, bedside tables, a round coffee table, and artwork on the walls.

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

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪1 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪6 min walk‬
  • Place, Mallory Square
    ‪12 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 min drive‬

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About the neighborhood

Key West

Old Town Key West stay.A stay at this Old Town Key West condo places you steps from Duval Street and within a 10-minute walk of Ernest Hemingway Home and Museum. Also, Mallory Square is within half a mile (1 km) and Florida Keys Beaches is within 2 miles (3 km).
View more Condo Rentals in Key WestOpens in a new window

What's nearby

  • Duval Street - 1 min walk - 0.0 miles
  • Ernest Hemingway Home and Museum - 6 min walk - 0.4 miles
  • Key West Lighthouse and Keeper's Quarters Museum - 6 min walk - 0.4 miles
  • Mallory Square - 12 min walk - 0.7 miles
  • Southernmost Point - 14 min walk - 0.8 miles

Getting around

  • Key West Intl. Airport (EYW) - 13 min drive

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Margaritaville - ‬3 min walk
  • ‪Moondog Cafe & Bakery - ‬5 min walk
  • ‪Mangoes Restaurant - ‬1 min walk
  • ‪801 Bourbon Bar - ‬2 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.

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

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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

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

  • No pets 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.

Property is also known as

Vrbo Property
2 bedroom accommodation in Key West Condo
Luxury Penthouse in prime Downtown location
2 bedroom accommodation in Key West Key West
2 bedroom accommodation in Key West Condo Key West
Rooftop Penthouse Luxury Penthouse in Prime Downtown Location
68f7aaa54d0afa001336cc6f

Frequently asked questions

How close is Rooftop Penthouse to the airport?

This condo is 3.8 mi (13-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

How much does it cost to stay at Rooftop Penthouse?

As of Aug 22, 2026, prices found for a 1-night stay for 2 adults at Rooftop Penthouse on Aug 23, 2026 start from $1,019, 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.

Does Rooftop Penthouse have an airport shuttle?

Airport shuttle services are not available at this condo.

How close is Rooftop Penthouse to the beach?

This condo is a short 13-minute walk from Florida Keys Beaches and 12-minute walk from South Beach. Don't forget your sunscreen!

Does Rooftop Penthouse offer free breakfast?

This condo does not offer free breakfast.

Is there a casino at Rooftop Penthouse?

No, there is no casino at this condo.

What time is check-in at Rooftop Penthouse?

Check-in begins at 4:00 PM.

Is there free parking at Rooftop Penthouse?

Free parking is not available at this condo.

Does Rooftop Penthouse have a pool?

This condo does not have a pool.

Does Rooftop Penthouse have a spa?

There are no spa services available at this condo.

How close is Rooftop Penthouse to downtown Key West?

This condo is 0.1 mi away from Key West.

Rooftop Penthouse Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 50 out of 55 reviews
Rating 8 - Good. 5 out of 55 reviews
Rating 6 - Okay. 0 out of 55 reviews
Rating 4 - Poor. 0 out of 55 reviews
Rating 2 - Terrible. 0 out of 55 reviews

9.8/10

Cleanliness

9.0/10

Amenities

9.0/10

Property conditions & facilities

Reviews

Verified review

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 review

10/10 Excellent

Libby S.

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

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

10/10 Excellent

William S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The balcony was great for people watching. Walked wherever we wanted to. The stairs were a surprise. Thank you.
Stayed 7 nights in Feb 2026
Verified review

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
Verified review

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 review

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 review

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 review

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 review

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 review

10/10 Excellent

Dave W.

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

Great Location and Fantastic Place

More then we expected. Place is even bigger then the pictures. Great location to hit the beach or the bars. Outdoor area is fantastic. Easy parking.
Stayed 2 nights in Jul 2023
Verified review

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 review

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 review

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 review

10/10 Excellent

Dr. Michael K.

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

outstanding premium property

This is an outstanding premium property in the heart of Duval Street. Hana was very responsive. Thank you for the memorable experience.
Stayed 5 nights in Apr 2024
Verified review

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 review

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 review

10/10 Excellent

Lawrence F.

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

Wyland Penthouse

Beautiful property in great Old Town location with all of the amenities! Fabulous stay in comfortable setting. Very quiet residence, even though directly overlooking Duval Street. It was cool to enter via "secret door" adjoining Wyland Gallery too. Walking distance to restaurants, tourist sites, and everything, even for 3 seniors! Fun time.
Stayed 4 nights in Sep 2020

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