Four bedroom Vacation Rental With TV | VaycayHero #28289

4-Bedroom Penthouse Condo with Shared Pool

Key West, FL (57) VaycayHero Booking Protection VaycayHero Booking Protection
  • Condo
  • 10 Guests
  • 4 Bedrooms BR
  • 4.5 Bath
  • Not Ok


About This Listing View Location >>

Beautiful four bedroom penthouse condo steps from the action has been recently upgraded. This four bedroom, 4.5 bath condo is in the heart of the action at Duval Square just south of Truman. The residential units sit in a courtyard setting above a retail/office courtyard below with the shared pool . There is no other condo like this at Duval Square. The penthouse home features a light and airy two story living room that has been freshly painted and redecorated with a tropical, fun elegance!. It opens to an adjacent family room area for TV viewing and equipped with a sofa sleeper.

There is also a brand new kitchen with new cabinets, countertops and appliances. Rounding out the first floor is a queen bedroom with private bath and laundry room. Up the circular staircase is three additional bedrooms each with bath ensuites, including a nice, large master bedroom. New carpet and fresh furnishings add to this perfect getaway. Easy walking distance to shopping, restaurants, art galleries, museums, groceries, entertainment, and the ocean with four bedrooms and four and a half baths, central air conditioning/heater with ceiling fans & TVs in all rooms makes for a relaxing, vacation destination. Beds:1 King, 2 Queens, 2 Twins, 1 Sleeper Sofa

Amenities include Central Air, Air Conditioning, Ceiling Fans, High Speed Internet, Private Washer & Dryer, Nice Furniture,  Shared Pool, Off Street Parking, Heated Pool, Close to Town.
Bed Configurations: Bedroom 1: King | Bedroom 2: Queen | Bedroom 3: Queen | Bedroom 4: 2 Twins | Living Room: Sleeper sofa.

Location Distance: Camille's Restaurant: 0.13 mi | Blue Heaven: 0.30 mi | Ambrosia Sushi: 0.31 mi | Antonia's: 0.32 mi | Flaming Buoy Filet Co.: 0.34 mi | The Green Parrot Bar: 0.36 mi | Santiago's Bodega: 0.36 mi | Sarabeth's: 0.36 mi | 2 Cents: 0.39 mi | Michael's: 0.47 mi | Azur Mediterranean Cafe: 0.61 mi | Danger Charters: 0.81 mi.

This unit is a part of Duval Square

This development extends from Duval Street to Simonton Street and is in the heart of historic Old Town. It is comprised of residential units upstairs and a variety of commercial units on the ground floor. In addition to the restaurants, there is a fine hair and nail salon, several Realtors (including us) and a tanning salon. Private, secured parking beneath the complex and security entrances provide you with peace of mind while in Key West.

Unique two bedroom two and one-half bath town homes located on the corner of Duval and Simonton in desirable old town Key West. The town homes are above all the action on the second level of the Duval Square complex. Covered parking for one car. Spectacular roof top pool for the guests use.

Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. All Duval Square Properties Have Use Of Heated Shared Pool, Lounger, As Well As A Covered Deck Area.

**Please note that not all of the amenities listed might be available to your specific unit. Please call if you have questions about complex amenities.**



Cable TV




Air Conditioning

Ceiling fans






Coffee Maker


Community Pool

Off-Street Parking

Host Details

Check In: 03:00 PM

Check Out: 10:00 AM

Rating: 57 5.0/5

Listings: 25

Member Since: 2015

Cleanliness Exceptional
Cleanliness Meets Expectation
Emergency Support
Emergency Support 24/7

1. Where will I pick up the keys from?
Detailed pick-up information will be provided to you once you book this rental.

2. I am going to be arriving late. Do I have to arrive during business hours to pick up keys?
You can check in any time you want on or after the check-in time. After-hours key pick up information will be provided to you once you book this rental.

3. Does the total price include everything? Are any of the fees refundable?
Yes, there is nothing more to be paid. All mandatory fees are included in the total price.

4. What is the cancellation policy for this rental?
Cancellation policy is listed on this page under 'Cancellation Policy'.

5. Is there a security deposit for this rental?


Please note that the cost of heating the pool is already included in the rates posted above. If you do not wish to have the pool heated, please let us know.

Host Rules: Age Requirement

Only allows family groups & people ages 25 and up. Rule is strictly enforced by the host.

Reviews (57)


Ed G.

on 04/21/2019

Great fun


Leah W.

on 03/28/2019

Beautifully renovated penthouse on Duval. Perfect location. Shad and Jann, from the rental agency were amazing.


Scott L.

on 02/07/2019

Wonderful central location very spacious


Elizabeth E.

on 06/02/2018

A great family reunion was held. The house was very well appointed. We had plenty of room for our family of 10. The kitchen was well equipped to cook for our family. Great location to walk to all of the places we wanted to visit in Key West. The only negative thing would be that the air conditioner was programmed and we couldn't figure out how to change it so the temperatures were warmer than we would have liked at certain times=but I'm sure the management company would have helped us with that if we had contacted them. It wasn't a game changer for us. We would definitely rent this property again.


Maureen K.

on 04/02/2018

Great location close to all good restaurants, shops and bars. The condo was clean, spacious and very comfortable, with a nice pool. Property management
Team was very helpful in recommending restaurants and activities.
Thoroughly enjoyed our stay. Thank you!


Jerry T.

on 03/11/2018

Staying at the Duval Square Penthouse was wonderful. My family and I had a great time.


Linda W.

on 01/25/2018

We loved our stay at Duval square condo! It was the best location to just about everything my son got married and I was able to get most of my family together! We had 4 fabulous clean bedrooms including a private bath! Thank you for letting us enjoy all you had to offer!


Stephanie P.

on 01/11/2018

Our stay in the Duval Penthouse was awesome. Perfect location right on Duval, yet tucked away inside enough so you're not bothered by nighttime noises or tourists. The penthouse had ample space for our group of 10 and more to spare; rooms were kept super clean and the place also had updated tech finishes like a Nest AC, remote controlled fans and keypad lock. Check in and out was smooth and Rent Key West had great customer service. Would definitely stay again and definitely recommend.


Tim S.

on 12/20/2017

Great location just off Duval street. Close to the action, but quiet.


Elaine S.

on 10/22/2017

This condo was beautiful! Went with our whole family and it was great to have a bathroom for each bedroom. The condo was well equipped with everything to cook in and also had beach towels! Had one small issue in master Bath and they came right away to fix it. Extremely satisfied. Great location, close to all but far enough away from the noise to have privacy.


Norman G.

on 07/16/2017

Lots of room, every bedroom has its own bath, great rental


Carlos S.

on 06/29/2017

Kid friendly and spacious. Great location and safe for those traveling with kids. Near excellent restaurants. The covered parking spaces (2) were ideal.


Lori M.

on 03/11/2017

This was our third year at the Duvall Square Penthouse!! We love everything about it...the size is great for four couples with each bedroom having its own full bath. The place is beautifully decorated and very clean. The location is nice and quiet and within walking distance to everything. We can't wait to go back next year!!


Sammi Jo D.

on 03/01/2017

We stayed the week in the Duvall Penthouse and it was wonderful!! Perfect amount of space, great kitchen, bathrooms in each bedroom! Perfect location on Duvall st. One of the agents even stayed open later for us to check in because we hit a lot of traffic! Only downfall was we could not figure out how to work the air conditioning.


Jan B.

on 02/11/2017

The condo worked out perfect for four couples. Each having their own private bedroom and bath made it perfect for sharing. Location was great, we only moved the car twice while there. The condo itself was very well supplied, we only had a few issues but were minor. Such as one bedroom lacking a mirror, and a fan in bathroom not working. The condo was clean but it is showing wear. Overall we all agreed we would return.


Stacy L.

on 11/14/2016

Duval Square Penthouse was nice. There was plenty of room for all of us.


Paul F.

on 11/08/2016

This unit was perfect for 4 couples. Each room had its own bathroom and enough common space to stay out of each other’s way. The location is perfectly located only steps from Duval and has great restaurants on the property. The area is very secure from the parking garage, keyed entry gates, to the key pad bolt lock on the house. This place was clean and ideal for 8 people on the go. I defiantly plan to rent this unit in the future. A+++


Catherine M.

on 08/26/2016

We had a wonderful experience at the Duval Square Penthouse. We found the Condo to be very spacious and clean. It was It had everything we needed including a well equipped kitchen and bathrooms as well as 8 beautiful beach towels. It was in Great location and people walked to their destinations all around Duval and Key West's points of interest. It also came in handy to have 2 parking spots in the lower garage.
The only negative to mention is that the condo was dated with worn carpet in some areas.
Rental company was helpful and courtious. We would rent there again should the opportunity arise to bring us back to Key West.


Norman G.

on 07/17/2016

A great condo, super location, I have rented houses in Key West for the past 7 years and this was by far the best.


Laura L.

on 03/05/2016

We enjoyed our stay in Key West. The property was nice, it could use a little TLC but overall nice. The location was a little far from all the action on lower Duval. The pool was a little sad, 4 feet at the deepest with a max of 12 people in the pool at one time. The rental office was wonderful to work with. Very helpful and pleasant.


Susan D.

on 01/24/2016

Overall we would definitely come back to this property. Many things were in good shape, the kitchen was well appointed. Only recommendations would be property upkeep in a few areas. Bath fan not working in upstairs twin room, upstairs queen is in need of new mattress, carpet in upstairs hall needs replacing, a couple light bulbs needed replacing.


Joseph L.

on 12/03/2015

Conveniently located, steps from Duval St, in the quieter side of Duval, but close enough to the action. We had an enjoyable stay. Plenty of room for 4 couples, nicely equipped kitchen, nicely decorated, clean.


Benny M.

on 10/23/2015

Great weather, roomy, well equipped, supplied condo at Duval Square. Queen size bed is too soft according to our guests of the last two years. Cleaning is adequate but mirrors and windows need a more through cleaning but overall a very comfortable, roomy home away from home.


Pamela B.

on 09/12/2015

I was overall pleased with the rental. Was disappointed it was 10 blocks from Mallory Square but I could have found that out before scheduling. My only complaint with the maintenance was we had no TV to watch as a group. It was not working when we arrived and after two repair calls it was not fixed when we left. Property was clean but could have had a little updating in a couple of the bedrooms....twin room especially. It was very spacious and I would stay here again in a heartbeat.


George G.

on 09/01/2015

We rented this property for a week for ourselves and visiting family during a Key West wedding of my daughter.
It was perfect......gorgeous, roomy, near everything, convenient, in other words, just perfect.
Check in and parking were a breeze. If you use the Key Shuttle, make sure to tell them to enter through the parking lot from Simonton.
We tried and loved all the restaurants down below in our very own plaza.
We even used the.option of having 2 of our guests use the quiet, private little alcove with the pull-out couch.
Having washer and dryer and all the bathrooms was a huge plus.
I would highly recommend this penthouse. It is worth every.penny!


Nikki M.

on 07/25/2015

We had a very nice time. The house was clean and very accommodating. We will be back!!


Anders T.

on 07/07/2015

We were 2 families staying for 1 week in July in this apartment. It is suitable fr 2 families with enough space for teenagers, smaller children and adults. Everything works well with an equipped kitchen and washing machines. The location in a quiet part of duval street and indoor parking for 2 cars was excellent.


Caril-Anne L.

on 05/15/2015

An amazing place to stay. Beautiful, comfortable, quiet and the location was perfect. I would definitely stay here again!!


Joan B.

on 01/24/2015

There were 4 adults and (2) kids staying in this condo and we never ran out of personal space. The complex is located off Duval Street making it to walk everywhere. The pool is located on the same level and has adequate sun and shade seating. There was a tremendous storm before we arrived and the patio furniture as drenched and patio quite wet leaving us unable to use it, but it was January and cool in the mornings and evenings so we really didn't miss it much, but it adds quite a bit of living space to the unit. All in all, we had a wonderful stay!


Alicia H.

on 12/27/2014

My family of 7 adults stayed in the Duval Square Penthouse for a week over the New Year, and we couldn't have been more satisfied. The property managers are directly below the condo, in a delightfully secluded, yet conveniently located on Duval, square with other restaurants and businesses. The use of the on-site pool was unexpectedly our reprieve; one can only "do Duval" for so long without taking much needed breaks, so we made the lovely and well appointed pool our haven. The condo was beautiful and roomy. The big screen TV was always on with a football game, the round table in the kitchen hosted many a card game, the dining table saw 3 delicious home-cooked meals and the beds were 5-star-hotel comfortable. We made good use of laundry facilities in the condo as well. While in Key West, we had a family photo made, using local photographer Rob O'Neal, (highly recommend,) we ate in the square at NY Pasta Garden (delicious and delightful,) we "did" tapas at Santiago's, which was perfect for 7, we rented jet skis, we charted a fishing excursion, we rented mopeds, we crawled Duval...I could gush more, but it would go on and on. We love Key West and will be back. With a large party, we wouldn't look elsewhere for accommodations: Duval Square Penthouse is top-of-the-list.


Sandra M.

on 11/20/2014

This place was awesome! Perfect for 4 couples. Plenty of room, 4 bedrooms with tvs, 4.5 baths. There was a gated garage with room for 2 cars. Everything was as described in rental information. Rental office was easy to work with. Very clean and well stocked. The only negative thing would be for the owners to provide some outside furniture covering for the seats outside on the patio as it did rain and we brought the cushions inside so they would stay dry. Besides that, it was Perfect!! I want to go back soon....


Beverly B.

on 07/23/2014

The place was great. Clean. Big. Lots of room. Location was perfect.


Eric T.

on 05/27/2014

The Duval Square Penthouse completely blew away our expectations. This gives you the cleanliness, professionalism, and service of a hotel, while giving you the feel of living in your dream condo. The location is a few blocks from the beach (we walked in our beach attire no problem) and minutes away from the chaos that is the heart of Duval St. I'd recommend this place to anyone it was absolutely EPIC!


Mary K.

on 03/16/2014

Five of us stayed here. Great location! Plenty of space for all! Only three stars for property location due to the constant Construction Work on the property...saturday and sunday it was blowers/gardening! They were there more than we were! But a great place! Would definitely come back.


David D.

on 02/22/2014

It was simply amazing. One week was not long enough


Kurt K.

on 01/12/2014

This penthouse has everything our party of 7 needed. Comfortable beds, quiet location, but with restaurants nearby. The only negative thing I can say is that there is construction ongoing in the lower parking garage during the day only. This was not an issue for us as we didn't come to Key West to sit in the condo all day, but parents with young children requiring naps should check with the rental agent to to see if the jack hammering below the condo has finished.


John K.

on 12/26/2013

Duval Square Penthouse was a nice place to stay. We had 8 adults on our trip and we had plenty of room for all. The only complaint I had was with the safe in the room. It was on a shelf that could of been ripped off of without much effort. I Didnt feel safe leaving anything in it. If you have a big group this is the place for you. Would stay again


Steve L.

on 11/16/2013

Although I'd specified that we would be using the sofa bed and that we'd like it made up, it was neither made up nor were there sheets until I could stop by the office on Monday. Office staff very friendly and helpful.


Glenn F.

on 11/05/2013

We had a small reunion of high school friends and had a wonderful time. Planning to come back in 2015.



on 04/13/2019

We love Key West Rentals. They are great and very helpful. Our rental was nice as always. We love the location and will rent through Key West Rental again. We had a small problem which I addressed with management and they were going to handle but everything else was perfect.



on 04/04/2019

Truly flexible process as we had multiple parties arriving and leaving throughout or stay which was handled amazing. Place was in great condition and recently remodeled. Spacious setup for our large group, pool was nice and low key when needed as well. Looking forward to being able to use the property again soon.



on 03/16/2019

The renovations made to the condo are absolutely beautiful. The location is very good, close enough to walk to most everything, but away from the loud night life.
It would be nice if the pool was heated a little. The cool nights really cooled the water off.
The staff at Rent Key West Vacations is very friendly and on top of everything. No complaints.
Highly recommend! We look forward to returning.



on 12/27/2018

Very nice condo with all the necessities, same level as the pool, close to elevators and private parking. Awesome view is Duval Street yet far enough away for quietness. Complex was clean and very well maiintained. Great unit for families or miultiple people. Worked great for our family of 9.



on 06/09/2018

Location- superb. Home was perfect in every way. Thank you Paul and Shad!



on 05/21/2018

Everything was really easy from the check in to checking out. We arrived late so we used the lock box to get the key to enter the property. Once inside we loved how clean and nice everything was. There was a water leak in the downstairs bedroom due to the amount of rain that week but besides that everything was great. Would book again if we ever went to KW with a large group again.



on 04/07/2018

Accommodations were great and rental agents wonderful. We hope to go back next year.



on 11/24/2017

This was our first time renting a place to stay anywhere and the process was very easy and straight forward. It is hard because you are staying in a unit owned by someone else, so I probably need to get over certain things. For example, the king size bed was way to soft and the pillows were very broke down and desperately need to be replaced. Maybe some folks like them that way? It certainly is not a hotel but would consider doing it again.



on 08/31/2017

The sales office was great at communicating instructions and what to expect when we arrived and left the rental unit.



on 07/11/2017




on 06/18/2016

We had a great stay at the Duval Square Penthouse. The rental was the perfect place our our group of 8. The condo was well equipped and in great condition with a perfect location. We could not have asked for more.. Also note that the parking included with this unit is a huge bonus. If you have ever been to KW before you will especially appreciate it!



on 12/27/2015

We had a mixed group - singles and couples - and this place was perfect. Every room had its own bathroom so we weren't tripping over each other getting ready. The place had rooms big enough to hang out together - and enough space to provide everyone their privacy. The kitchen had everything we needed for eating in and the dining room table was large enough for a family-style dinner. Everything was as good as what it looked like in the photos. We would definitely consider this again for a large group.



on 12/19/2015

The penthouse was clean and well-equipped. Plenty of room for our family of five adults, plus 6 other visitors the first two nights.
It's a great location on Duval Street, but still really quiet in the unit.
Only real complaint in the unit itself is the lighting in the kitchen. If you are going to cook dinner there, it's going to be in the dark. They need under cabinet lighting or at least to replace the light over the stove.
There is a balcony on both levels of the unit, but not much of a view, and we were kind of surprised there wasn't a grill. So, we didn't spend any time out there, but we did spend some time at the pool.
Skip the crowds and restaurants on Duval and go to all the great places on Petronia Street.
Joyce at Key West Vacations was very helpful.



on 07/19/2015

This condo was very spacious for our large party. The location was perfect! When you think of Duval St, you don't think that you'd be in an area that was quiet. We were! They was so work being done during the day, but you couldn't hear it from inside the condo. I sent many emails prior to our trip, and they were all answered in a timely manner. Make sure you go to Panini Panini! We probably went there 5 times during our stay.



on 06/28/2015

Location is great. Property is spacious Only minor little things could use attention. Chair in first floor bed room in bad condition. Outside deck looked like a storage area. Bath tub outside -- very creative. Woul rent it again.



on 04/16/2015

My friends and I rented this house for a bachelorette and I was the bride. The house was very roomy, clean and in a perfect location to all the restaurants, beaches and bars. The house made our trip and we hope to plan another soon.



on 11/15/2014

The unit we rented was absolutely perfect for our needs. We had 8 people living in here for five nights and the arrangements worked out great. The unit is open and airy, and has a nice warmth that make everyone want to sit in the great room and converse.

The kitchen area is well kept, and great for dining in.

The condition of the unit was also well kept, though, the sliding doors need to be replaced. We used the outside patio often, and the doors became a hassle.

The location was also perfect for our daily walks to the beach, the parks and the clubs.

All of the beds have very good mattresses and everyone slept comfortably.

The pool was a little small, but was nicely situated and private.

Only other minor annoyance was the showers. The faucets had to be carefully turned back and forth to get the hot water to come out. Don't do it right, and you're having a cold shower.



on 04/12/2014

This Rental truly exceeded our expectations. The picture to not show how large the unit actually is. There was plenty of seating space with a nice out door sitting area. We had 8 people staying in the unit and did not feel crowded at all. It was a spectacular stay!


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