Five bedroom Vacation Rental With Ocean View | VaycayHero #28257

5-Bedroom House with Private Pool & Jacuzzi Tub

Key West, FL (61) VaycayHero Booking Protection VaycayHero Booking Protection
  • House
  • 12 Guests
  • 5 Bedrooms BR
  • 4.5 Bath
  • Not Ok


About This Listing View Location >>

Luxury on Duval Street in historic Key West? Luxury is not what most people visiting Key West associate with Duval Street until you look at Dreaming On Duval! There are very few private homes on Duval, let alone a single family vacation rental that is steps away from everything Key West has to offer and accommodates up to 10 friends & family members for a relaxing vacation with everything you could ask for. This beautiful home will be featured on an upcoming episode of HGTV's House Hunters.

This spectacular home features five bedrooms and four baths on three floors with approximately 4000 square feet is perfect for family reunions, best friend getaways and even wedding parties. Just south of Truman Avenue with a deck overlooking Duval Street this a location to Dream about! Entering the home through a beautiful mahogany door you come into the library lined with custom cabinetry, a perfect place to relax with a book of your choice.

There is one bedroom on the first floor with a king bed and bath en-suite. This bath doubles as the powder room for the first floor. Then you enter the heart of the home facing to the backyard. The open concept design of the kitchen, dining and living room invites the guests to gather and socialize. This space opens to a large porch and deck area by the "conversation" pool. There's room for everyone to lounge in the heated pool sharing stories of your day or the last time you saw each other.

The kitchen is completely equipped with high end appliances and dishware. The living room has a large flat screen TV and stereo system with speakers throughout the first floor including iPod jack & mp3 player. Plan a nice dinner in and enjoy the dining table for up to ten (twelve if you squeeze) or choose to sit outside on the front or back patios for dining al fresco. The "grand" staircase leads up to the second floor and a computer/lounge area. Perfect for reading a book, surfing the web or uploading photos of your vacation.

This is also a great place to occupy the kids with a dvd, Through the lounge you can enter two similar bedrooms. Walk through the bedrooms to the shared bath with a view of Duval Street. These bedrooms offer versatility with either two twins in each room or a king in one or both. Step into the second floor master suite and feel like you are stepping into your own personal spa. The room with it's cool spa green colors has a beautiful four poster wood king bed with a sitting area to read, relax or enjoy a movie. Step out the sliding doors to a large relaxing deck over looking the pool area.

The master bath is a true luxury with it's dual sinks, large walk-in shower and spa tub. If the second floor master isn't your choice, then make the final journey up to the third floor of the home to a junior master suite complete with wet bar, sitting area and king bed. This third level porch overlooks the pool and offers a glimpse of an ocean view and several Key West historic properties including the Key West Lighthouse. Make this the vacation you have always dreamed of at Dreaming on Duval!

Amenities include Central Air, Air Conditioning, Ceiling Fans, Jacuzzi Tub, High Speed Internet, Blowdryer, Private Washer & Dryer, Nice Furniture, Deck, Patio, BBQ Grill, Gas Grill, Private Pool, Off Street Parking & Heated Pool.

Bed Configuration: Bedroom 1: King | Bedroom 2: King | Bedroom 3: King | Bedroom 4: 2 Twins | Bedroom 5: 2 Twins | Living Room: Queen Sleeper.

Square Footage: 4000 Square Feet.

Location Distance: Camille's Restaurant: 0.16 mi | Blue Heaven: 0.25 mi | Santiago's Bodega: 0.30 mi | Antonia's: 0.32 mi | Ambrosia Sushi: 0.34 mi | The Green Parrot Bar: 0.34 mi | 2 Cents: 0.38 mi | Sarabeth's: 0.38 mi | Flaming Buoy Filet Co.: 0.42 mi | Michael's: 0.52 mi | Azur Mediterranean Cafe: 0.66 mi | Danger Charters: 0.80 mi.


Ocean View



MP3 player



Air Conditioning

Ceiling fans







Coffee Maker





Cable TV



Off-Street Parking

Host Details

Check In: 03:00 PM

Check Out: 10:00 AM

Rating: 61 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 (61)


Gerard P.

on 05/24/2019

This house has everything you can hope for and more. Truly a luxury vacation accommodation. Great location on the less traveled section of Duvall Street, but a close enough walk to everything.


Scott P.

on 05/08/2019

Great house for our company retreat during the Songwriters festival. Hope to get the same place for next year


Chris C.

on 04/25/2019

Went with a group of 8 and had an absolute blast. House has plenty room, and more than well-equipped for cooking at home if you want (we cooked our catch one night). Pool/patio area was excellent and never felt too small for our group.

Would 100% come back again - maybe with a larger group though because this house can easily handle much more than 8 people.


Helen E.

on 04/16/2019

We spent a fantastic week at this amazing home. Our kids with their kids joined us for our 40th anniversary.

The home was perfect. Very clean and well equipped. Elegant in a casual way, large but still cozy.

We had six adults and four kids and each family had some private space and comfortable quiet sleeping. The decks took our collective breathe away!

Dreaming on Duval provides great people watching from the front porch, it’s close to everywhere you want to be and offers complete privacy and peaceful fun at the pool in back- all in one beautiful package!

Property managers are terrific. House has it all.

We want to come back!


Laura D.

on 01/14/2019

Excellent- we thoroughly enjoyed the property and appreciated how easy it was to check in/check out. It was a wonderful house- perfect for the 9 of us and with a nice outdoor space. It was also an ideal location for walking around Old Town. We had a wonderful time!


Lawrence W.

on 10/29/2018

This is an absolutely positively spectacular home with all the amenities anyone could possibly ask for. The beds and furniture were very comfortable. The entire home was spotless. The decor was beautiful. And the location could not have been better for a fun-filled stay in Key West. Also, every single person we had contact with at Rent Key West Vacations were extremely professional, friendly and accommodating especially Jann and Joyce. We will definitely be back again as soon as we are able!


Marvin M.

on 07/28/2018

Perfect home, great service.


Kathleen U.

on 07/08/2018

We have been coming to Key West since 2002 and this year we brought our grown children with us (the youngest was finally 21!) The house was perfect for us to all be together for morning breakfasts, laying by the pool, etc. It was a beautiful house, and the pool was great for cooling off from the tropical heat.


Kathleen M.

on 06/04/2018

My family had a terrific vacation. The home was beautiful, pictures do not do it justice. In the heart of Duval, we were able to take advantage of all the great restaurants, bars, shops and galleries.I hope o go back with my family again!


John M.

on 04/05/2018

We rented the house for our family to stay for a 50th Birthday and for our wedding. Ten of us stayed at the house and we had plenty of room! The house was immaculate, the pool was perfect to sit in and relax. And the location is perfect! We had zero problems, never had to contact management. One of our favorite things was sitting on the front porch and mingle with the people walking by. Highly recommend!!


Jane P.

on 03/27/2018

Terrific house for family with five adult children and their significant others. Space for everyone all over the house. And so clean and neat! Decks, patios, and porches offered backyard privacy and chill time, or sitting by the front door watching the action on Duval Street. The rooms are spacious with great bathrooms and comfy beds and linens. The location is just the best for walking everywhere. No car is necessary. Great sound system and tvs abound. The pool is tiny, but perfect for cooling off. Really a great vacation rental with attentive management for any questions or needs.


Amy M.

on 03/11/2018

Dreaming on Duval was the perfect house for our family! Each person had their own area of the house. It was decorated superbly! Also, we did not hear any noise from Duval. It was close to everything we wanted to do. I would highly recommend this house!!


Cody W.

on 03/07/2018

This place is incredible, if you're thinking about finding a very upscale rental, this is hands down your place. Huge rooms, excellent location, can not say enough about this property. Absolutely 100% perfect.


Michelle M.

on 01/27/2018

We had a fantastic vacation at this house! We have 4 adult children-2 with significant others-and were very comfortable with this house as a family of 8 adults. It is perfectly located and the house was clean and very well equipped. The fencing and landscaping made us feel we were all alone in our own space, but out the front door, and there was the action of Duval! We plan to be back soon!


Bart L.

on 01/10/2018

12 people stayed and had a wonderful time. Really can't say enough good things about this property. Super clean, beds were all very comfortable. Surprisingly spacious; pictures don't do it justice. Simply amazing and would highly recommend!


Joseph D.

on 11/13/2017

We had nine adults and one child and this house easily accommodated all of us. Great back patio and pool area. The house was centrally located and easy walking distances to all locations. A top notch facility.


Natalie H.

on 08/24/2017

I recommend this house to absolutely everyone. The house was absolutely gorgeous, the pictures do not do it justice. The house is very spacious and the outdoor area feels like a little oasis.


Christopher H.

on 07/06/2017

I rented for my brothers bachelor party. We easily had room for 10+ people. I passed out on the couch multiple times. The kitchen was amazing and new. Everything was clean. I loved this place and I typically stay in 4/5 star hotels. My one issue was the grill was out of propane - but he said he would replace the next day.


Susan M.

on 02/08/2017

great vacation in a lovely home--neighborhood a little disturbing


Doug B.

on 01/26/2017

House was everything as advertised. Check in fast and easy. Location great and quite at night. A couple of minor problems that were fixed immediately.


Marcy P.

on 10/06/2016

Loved staying here. There was plenty of space for my very large family. I would definitely stay here again.


Elizabeth G.

on 09/29/2016

What an absolutely fabulous time we had celebrating my husband's 50th at Dreaming on Duvall. The location is great and the management company was responsive and provided excellent customer service. The house is beautiful and easily accommodated 10 adults. I would love to return and would highly recommend this property


Leshia and Chris L.

on 05/28/2016

Amazing property with plenty of room for 5 couples. Decor and amenities were modern and comfortable. A real gem on Duval St.

Only room for improvement is speed of wireless network and door alarms are very sensitive and would go off randomly and say certain doors were open. We never really figured out what was going on with it.


Paula H.

on 05/08/2016

We had a wonderful time in Key West for my husbands 50th birthday. Dreaming on Duval was the perfect location for us and our guests. Rent Key West were a wonderful company to deal with. We left a few things behind and offered to send them back to us, which we certainly appreciate!


Jamie P.

on 04/21/2016

Dreaming on Duval exceeded our expectations! This property is beautiful, clean, comfortable and within walking distance to everything our group wanted to see/do. I would whole-heartedly recommend the property management company and this property to any family looking for a one-of-a-kind vacation. We will be back.


Carolyn B.

on 03/28/2016

We had a superb experience! Duval is so busy, but this home is located on the quieter part, plus the house is so insulated noise is at a minimum. It's beautifully appointed and close to everything. We walked to Hemmingway's home, Trumans summer home, restaurants, the beach, church, sunsets, shops, the aquarium, etc. the splash pool was perfect,me specially for our little granddaughters. It was a dream vacation.


Anjanette K.

on 02/19/2016

An absolutely delightful week in a beautiful home! The house could not have been any better for my 40th birthday celebration with family and friends. The location was great, and this sprawling house was perfect for our large group, givingbus plenty of space to visit as a group, and allow everyone some quiet time, too. Amenities were perfect, and Rent Key West was accommodating, welcoming, and helpful. Could not have asked for a better experience- thank you!


Ryan S.

on 02/11/2016

The pictures do not do this home justice, it was a truly incredible property. We had 10 people staying there and in no way were you ever crowded as the vast home provides both seclusion coupled with great gathering space. The kitchen and the back porch/ pool was the perfect space to host and have fun. The accomodations also provided a very functional decor that was at the same time elegant. I would definitely recommend this property to anyone.


Robert F.

on 09/02/2015

Wonderful as always, a second year and can't wait to come back a third


Randy P.

on 05/30/2015

We were in Dreaming on Duval for my wife's 65th birthday. We and two of my wife's sisters and their husbands enjoyed our stay in this spacious and well kept house. Everyone had plenty of room, the beds were comfortable, and we enjoyed the outdoors as much as being inside. The pool area and front porch got plenty of use. On one rainy evening the comfort of the front sitting room was wonderful. The rather central location on Duval with the Blue Sky rental agency right next door was perfect. We ate all of our meals except one at Dreaming and the pots, pans, utensils, etc. provided were plentiful enough that we had no problems preparing any of the meals from our Key West cookbook. The dishwasher got quite a workout also. The fridge was spacious enough for all of our perishables and drinks, although the non perishable food storage area was a bit tight. The service we received from Rent Key West was outstanding. We had three lack of knowledge on our part issues concerning the TV/DVD system, the gas BBQ, and the pool. In each case we called RKW and Seth was at the door within five minutes to show us how to use the equipment. Thanks Seth, you were our hero! It might be time to evaluate the gas BBQ, but it got our steaks, brats and dogs cooked nicely. Hey, a Big Green Egg would be a crowning piece for this wonderful property. In summary my wife loved the property and the great birthday week it provided for her and our family. Add in the fishing, snorkeling, beaches, historical attractions, Mallory Square sunsets, shows, and shopping and you have one great birthday week celebration.


Ernie S.

on 04/30/2015

The location is perfect! We were in walking distance to every where. The home was beautiful. The beds were very comfortable. The private back yard and front porch was extra special. The kitchen was perfect and room for all to gather around. The family did not want to leave home. Perfect family getaway. Will go back again. Peaceful, Beautiful and very Top Notch!


Bill M.

on 04/22/2015

House was well equipped and furnished. Its location was centrally located with easy accessibility to restaurants and activities.


Carol L. S.

on 04/04/2015

We loved everything about the house and the location. The rental staff were extremely helpful. We had a wonderful time and look forward to returning.


Jane D.

on 01/04/2015

This home has it all - beauty, comfort and location. Brad (from Rent Key West) came to our rescue after our first rental fell through at the 11th hour. From check-in to check-out, Dreaming on Duval was truly our dream come true! Great layout if you have a large group and want some privacy, and the LR, DR and kitchen are large enough when everyone wants to be together! We just loved everything about this house! Thank you!


Elizabeth K.

on 11/22/2014

Our family had a wonderful week staying at Dreaming on Duval. The beautiful house was stocked with everything you needed. It was so quiet and peaceful even right on Duval. Having the key pad entry was perfect. Only thing that needs to change was the WiFi signal was very weak and would only work right on the 2nd floor.



on 08/16/2014

Dreaming on Duval was the perfect home to host my family and friends for my 50th birthday party. The home is beautifully decorated and spacious. We loved that the main floor kitchen was central to those choosing to hang out in the living room, sit at the dining room table, or lounge by the pool. Overall, a great place for a group that chooses to travel together!


Eleanor T.

on 08/09/2014

We had a wonderful week staying in Dreaming on Duval! It is in a great location on Duval Street and very convenient to most everything! However, because of the orientation of the interior of the house, you don't hear the street noise and the pool area in the back is like a hidden oasis.
The house is fully equipped with everything needed for a great stay and Key West management was wonderful to deal with. Also, their new concierge service is great! We used them for everything from rentals to reservations to just getting information.
I would highly recommend this property to anyone wanting a vacation in a beautiful home away from home!


Mimi C.

on 06/08/2014

This home was not only beautiful but perfect location. It offered everything we needed. Lots of space, great backyard with pool and waterfall. If I won the lottery, I would consider buying this home should it go on the market.


Lawton S.

on 02/15/2014

The House and location are great. A new or more comfortable sofa in the living area would be nice. But all of agree, GREAT HOUSE!


Michael M.

on 11/16/2013

After finishing a 165 mile bike ride from Miami to Key West, checking into DREAMING ON DUVAL was exactly that…a dream! The place is the perfect place to host a small group of people and perfectly located for everyone to get around town...



on 05/12/2019




on 04/03/2019

Was a dream come true! Exceptional house for a family gathering to celebrate.



on 01/06/2019

Family get together in Key West
The house was everything we were led to believe and more. Everything was in good working condition and when we had a couple of issues they were corrected the same day. We have two small grandchildren so the small pool was the perfect size for them. And, the beach is only a couple of blocks away.

We would definitely stay here again and hope to do so in the future.



on 10/14/2018

Awesome place



on 04/14/2018

This is our third time renting this home and was enjoyed as much the last as the first. Spectacular home perfectly located and comfortable for our large group of twelve people.



on 10/18/2017

When we walked into the house we were amazed that it was even more beautiful in person than in the photos. And amazingly clean. Everything was there that we could have needed and more. Nothing like staying right on Duval! Awesome experience!



on 07/10/2017

fabulous home, right on Duval, yet exceptional privacy
home was super clean, accommodated ot family of 8 perfectly. loved this home - we are house renters on vacation, and this home was the best yet (and we rent luxury homes) when back to key west, would stay nowhere else, but here. Rental company allowed a late checkout as we had a late flight out of Miami - perfect



on 06/22/2017

Our family with 12 members, ages from 3 to 75, enjoyed our stay in Key West on Duval St. It was hot and humid, and the children enjoyed the pool. Lots of bedrooms and beds. Manager got right on any small issues we had.



on 03/25/2017

My family and I have rented vacation homes around the world and this home is among the very best. Well managed and maintained by Rent Key West, superb location in the heart of Old Key West, well appointed to ensure your every convenience and a spaciousness that allows everyone privacy if desired or gathering places to enjoy family fun activities. The home is within easy walking distance to all major Key West attractions, the beach, shops, and numerous restaurants.

A wonderful venue for any gathering of family and/or friends.



on 12/03/2016

Tremendous property! The actual property is as beautiful and nicely designed as the pictures suggest, so I will focus just on the things that struck me and caused the property to significantly exceed my expectations:

The property is very large: the inside of the house is more spacious than you would expect, which is nice because your group will not feel like they are on top of one another. This is true of the outside of the house too: there are sitting areas in the front of the house facing Duval (with nice privacy fence so you see pedestrians but they don't notice you), on the side of the house where the grill and picnic table are situated, around the pool and back patio, and 2nd and 3rd level decks.
The location is awesome: you can face the activity on Duval when you want but the property is so long that the back of the property where the pool is feels very serene and secluded. Just awesome.

Definitely coming back!



on 10/31/2016

We could not have been happier with the home. Photos on the internet do not capture the spaciousness of the home. We used Dreaming on Duval as a home base for our son's wedding. Everyone loved gathering in the house.



on 08/05/2016

We celebrated my wife and daughter's birthdays with the whole family. We all enjoyed staying here. It was the most relaxing home and the property well maintained. We would most definitely come back.



on 05/21/2016

We had a wonderful family vacation primarily due to our ability to all stay together in one home. The property Dreaming on Duval was absolutely beautiful with great attention to detail. The house was well decorated and supplied and has been very well maintained. We as a family unanimously agreed that we would absolutely rent the property again when returning to Key West. It is a five star property that we would recommend to friends, family and anyone reading this review. YOU WILL NOT BE DISAPPOINTED!!!



on 11/19/2015

There were 10 of us for over a week and Dreaming on Duval was perfect! There is so much space to spread out so everyone doesn't have to be in the same space all the time. There was plenty of outdoor seating around the pool. The front porch was a fun place to sit and watch the activity on Duval. Rent Key West were FANtastic to work with. There were plenty of dishes, glasses, silverware, drink-ware, towels, beach towels for 10 people. Plenty of dining space. It was sooo nicely decorated. Truly a delight to be there. We were in Key West for a wedding so we had a continual stream of wedding guests stopping by because we were right on Duval. Beds were comfy. Huge washer and dryer. It was perfect!



on 10/06/2015

great house, great location, very clean, very comfortable, would stay here again



on 03/27/2015

Our group had a ball! Fabulous house and great location.



on 01/29/2015

Dreaming on Duvall was a wonderful experience for our group of 10. It was spacious and beautifully appointed. The heated pool was a plus for the few chilly days. It was the perfect location. Everything was within walking distance. The property management company was accommodating and available to answer any questions we had. A fun, fabulous experience!



on 12/20/2014

This was our family's 2nd trip to this beautiful home. Christmas made it even more special! The staff is wonderful especially a lady I believe her name is Joyce she always had the answers to any questions!



on 10/15/2014

Everything went smoothly and perfectly. We stayed there 4 nights as part of a corporate retreat, in mid October. We were nervous about the start of Fantasy Fest but everything was (mostly) PG and all in the business felt comfortable.
Checkin took 5 minutes max and was pleasant. House was clean, beautifully furnished and AMAZINGLY quiet for being on Duval Street. The backyard was perfect for the long weekend and it was even better when the pool heat was on and waterfall flowing.
Sound system and electronics worked great after a quick call for help to Rent Key West.
Highly recommended, I (and my colleagues) plan on returning as a company and with our families.

My only (very minor) gripes: no hair conditioner in the shower
Chairs at dining room table weren't the most comfortable (but then again we were at our computers for 4 hours a day)
Couch in front room could have been a foldout for more space
More "aesthetic" outdoor lighting by the pool



on 08/27/2014

The title says it all, the house was great for a large family. It had plenty of room, bedrooms were perfect and upscale. The house was so nice we spent more time there than anticipated. House is right on Duval but on the southern end. The house was very quiet at night but all attractions were walkable.



on 05/22/2014

we had a wonderful stay at this property and ended up having wedding ceremony poolside instead of going to the beach. clean, beautifully decorated, as advertised. only issue was the jet tub in master bath didn't work, and the jetted tub was one of the reasons we chose this property, that was a big disappointment.


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