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Dreaming on Duval - Nightly Rental

5.0000
(36 Reviews)

Capacity

5 Bedrooms
4.5 Bath
Sleeps 10

Search Availability

About

THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a private wonderland on the quieter end of Duval Street. Enjoy morning coffee or people watching on the elevated, partially covered front porch. The home’s backyard oasis includes a covered rear patio, a pool with waterfall feature and lush landscaping. A gas grill and outdoor furniture allow you to dine under the stars. Alternatively, enjoy dining in the open chef’s kitchen with adjoining family room. Expansive glass doors allow you to see the kiddos from this spacious area. Stainless steel appliances, 2 Keurig coffee makers,granite countertops with seating, white cabinetry, and an island with gas cook top adorn the kitchen. Friends can help with meal prep while enjoying cocktails and conversation.

Vacationing with a large family or wedding party? Dreaming on Duval will accommodate your crowd. With three levels of gorgeous living there is plenty of space for everyone to stretch out. The first floor includes the family room, kitchen, powder room, and study-a suitable place to work/school virtually or enjoy a quiet read. A first-floor king bedroom with luxurious ensuite bath walk-in shower is ideal for the in-laws.

The second floor is home to three additional bedrooms, separated by a hall workspace and full-size washer and dryer. The primary king suite is located at the rear of the home and includes a relaxing sitting area, desk, wet bar, and private balcony overlooking the pool. Its dreamy bath has double sinks, storage, a large walk-in shower, and separate spa tub. The twin bedrooms at the front of the home share a splendid Jack and Jill bathroom with walk-in shower. The sunny third floor with skylights is home to another private king bedroom with ensuite bath, dual sinks, and walk-in shower. It has a sitting area, wet bar, and workspace. Its covered balcony provides a view of Key West’s lighthouse, adding to the dreamy seclusion of your space in the clouds.
Dreaming on Duval is a sizable home (approximately 4,000 sq ft) with an ideal layout for larger families, wedding parties or groups of friends. In addition to private spaces and indoor-outdoor living, this designer home with hardwood floors, TVs and ceiling fans is impeccably furnished throughout. Come enjoy this beautiful home away from home on world famous Duval Street!

BED CONFIGURATION: The first-floor bedroom includes a king size bed and ensuite bath. The second floor includes three bedrooms. The primary king bedroom includes a large ensuite bath and balcony. Two additional twin bedrooms on the second floor share a Jack and Jill bath. Each of these bedrooms has two twin beds that can be converted to kings. The exquisite third-floor king bedroom has an ensuite bath and private balcony.

OUTDOOR AMENITIES: The tropical outdoor area has shaded areas for sitting and dining, as well as sunny areas for lounging by the private pool. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. Enjoy the sound of the waterfall feature while sipping on a cocktail or cooking on the gas grill. In no time, you will know why this house was featured on HGTV’s House Hunters. PLEASE NOTE: THIS IS A NON-SMOKING PROPERTY, INSIDE AND OUTSIDE. Additional fees will be charged if evidence of smoking is detected.

PARKING: There is designated parking space for one vehicle, which is a luxury in Key West! Plenty of space for scooters or bicycles.

LOCATION: Upper Duval Gallery District. Close to the Hemingway House, Key West Lighthouse, Butterfly Conservatory, and many top-notch restaurants, cafés, and bistros.

PETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that are pet friendly).

SMOKING: This is a non-smoking property, inside and outside.

***Guests must be 25 years of age or older unless accompanied by an adult***

***Managed by Historic Key West Vacation Rentals***

Features

Amenities

  • Television
  • Air Conditioning
  • Coffee Maker
  • Dishwasher
  • Microwave
  • Toaster
  • Heated Pool
  • Private Pool
  • Full Kitchen
  • Gas Stove
  • Cookware
  • Dinnerware
  • Central Air
  • Ceiling Fans
  • Linens
  • Washer & Dryer
  • Ironing Board
  • WiFi High Speed Internet
  • Iron
  • Hairdryer
  • Private Balcony
  • Private Yard
  • Gas Grill
  • Parking space
  • Cable TV

Location

  • Historic Old Town

Type

  • House

Length of Stay

  • Nightly and Weekly
  • Yes

Video

Availability

Key
#Night Available#Night Unavailable#Arrive Only#Depart Only
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Map

Reviews

Great Family Trip

November 2024
, Arlington, VA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Somehow the pictures don't do the house justice - it is huge! We spread out across three floors and it was wonderful. Grandparents in the main level master, parents with kids on the second floor, and another couple upstairs. We only had 8 but could certainly sleep many more. The pool was perfect size for toddler kids to swim back and forth and great for older folks to soak in too. The management company is incredibly responsive and helpful. I was worried about noise on Duval but it wasn't an issue at all - its a quieter end of the street. 10/10 would stay again!

Manager's Response

10/10 we expect you to come back soon! Thank you for the kind review ~ I think it gives future Dreaming on Duval guests an idea of how wonderful the home is. We look forward to seeing you again soon!

~ Jennifer & Team @ HKWVR

Dreaming on Duval

November 2024
, Kernersville, NC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Fabulous property - very spacious and warm. All the comforts of home with ample seating for a meal, an outdoor conversation or gathering in the den.

Manager's Response

We are so happy to hear you enjoyed your time at Dreaming on Duval! We hope everyone will come back for some more making memories Key West time.

~ Jennifer & Team @ HKWVR

Absolutely Perfect!

October 2024
, Richmond, TX United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Our family of 9 ranging from 14 to 77 yrs old enjoyed this lovely property while in Key West for our Granddaughter’s wedding. Everyone had their “own space” and the location was perfect for walking almost anywhere we wanted to go. I have to confess, this is a picky bunch and Everyone Was Thrilled!

Manager's Response

We are so happy to hear *everyone* enjoyed Dreaming on Duval! We hope you'll come back again, maybe for another joyful event.

~ Jennifer & Team @ HKWVR

40th birthday surprise!

September 2024
, Glenwood, NJ United States

Overall
5
Services from rental manager
4
Cleanliness
5
Location
5
Property condition
5

This was my first time to key west and this house definitely elevated our experience! The 3 main bedrooms were super spacious and the communal spaces, both indoor & outdoor, were great especially for our party of 10. Despite the property being directly on Duval street, once inside or in the backyard, you felt very private. The rental company were lovely to work with every step along the way and even checked in during our actual stay.

Manager's Response

We are so happy to have been a part of your first time in Key West! We look forward to your second!

~ Jennifer & Team @ HKWVR

Peaceful Vacation!!

August 2024
, Allen, TX United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The house is amazing. Great for a large group and set up for hosting for sure. The location is perfect. We had an amazing time.

Manager's Response

What a nice review and we're thrilled you enjoyed your time at Dreaming on Duval! Please come back again soon.

~ Jennifer & Team @ HKWVR

AWESOME!!!!

August 2024
, Jeffersonville, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We have stayed at this property several times and look forward to coming back every year. Perfect house, perfect location, perfect everything!!!!! Historic Key West Vacation Rentals is alway great to deal with!

Manager's Response

Thank you so much for being a repeat guest (we value you!) and for the kind words about Dreaming on Duval (and about us!)! We can't wait for your next visit!

~ Jennifer & Team @ HKWVR

AWESOME!!!!

August 2024
, Jeffersonville, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We have stayed at this property several times and look forward to coming back every year. Perfect house, perfect location, perfect everything!!!!! Historic Key West Vacation Rentals is alway great to deal with!

Manager's Response

Thank you so much for being a repeat guest (we value you!) and for the kind words about Dreaming on Duval (and about us!)! We can't wait for your next visit!

~ Jennifer & Team @ HKWVR

Fantastic Location and Beautiful home

July 2024
, Reydon, OK United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Dreaming on Duval was walking distance to most everything , but we did rent a golf cart through HKWVR. The furnishings were both comfortable (including all the beds)and beautiful. Space was great for our extended family of 10. We loved people watching from the front porch, cooling off in the pool, and walking to dinner, shopping and many sightseeing stops. Management company was excellent with communication.

Manager's Response

Thank you, Stacy, for your excellent review of Dreaming on Duval! We agree it is a great home in a fabulous location! And we are happy to hear that we communicated effectively. Come back and stay with us again soon~ Lori @ HKWVR

Great Girls Getaway

June 2024
, Independence, Or United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This was an excellent house in the most perfect location for our girls trip to Key West. The house and property are extremely well maintained. The property location is right in the heart of the Duval area. There are so many shops and restaurants with in walking distance. Our stay was perfect!

Manager's Response

We are so happy you had a good time at Dreaming on Duval! We hope you and the Girls will make it back (together or separately) to stay with us again.

~ Jennifer & Team @ Historic Key West Vacation Rentals

Dreaming on Duval

April 2024
, East Stroudsburg, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

One of the best luxury rentals I have stayed in. Comfortably accommodated 8 guests --well laid out living arrangements, clean, convenient and lots of little touches to make the stay special (outside ice machine, pool towels, etc) and the staff at Historic Key West Vacation Rentals were great to deal with--helped us with golf cart and bike rentals, let us leave their luggage at their office until house was ready, etc. Top notch experience all around

Manager's Response

We are so happy to hear you enjoyed your time at Dreaming on Duval! We hope you'll come and stay with us again, and soon.

~ Jennifer & Team @ HKWVR

Family vacation to Key West

April 2024
, Charlottesville, VA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Lovely place. Lots of room for two families. Very private. Ideal location. Would definitely stay here again!

Manager's Response

So happy you enjoyed Dreaming on Duval. We hope when you say you'll stay again, you mean soon!

~ Jennifer & Team @ HKWVR

Heaven on Duval

March 2024
, Niles, OH United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

House is perfectly located in Duval. Clean, perfectly appointed (attention to every detail), rooms are spacious and professionally decorated. HKWV responded promptly to any question during our stay. Home is secure. Bedding is luxurious. Definitely high end. Will definitely book again if we go.

Manager's Response

Thank you for noticing our operations teams' attention to detail. They work hard to make our homes beautiful and clean for you. Please come and stay again!

~ Jennifer & Team @ HKWVR

!016 Duval was Spectacular!

February 2024
, Bethesda, MD United States

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
5

Our family traveled to Key West for a family wedding. There were four families in this home. It was perfect for our needs, It was well located, nicely appointed and offered lovely in side and outside eating areas.
had wonderful amenities, including a lovely seating area around the pool.

Manager's Response

So glad you enjoyed your time at Dreaming on Duval. We love to hear that you had a good time and enjoyed this beautiful home.

~ Jennifer & Team @ HKWVR

Sun in February!

February 2024
, Charlottesville, VA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had a great time celebrating my 80th and 44th birthday of one of my daughters. Loved the location (quiet end of Duval) with many shops, restaurants and ice cream near by. Lots of room for our growing family (10 of us). Very clean and top-of-the-line appliances.

Manager's Response

Thank you for taking the time to review your stay at Dreaming on Duval. We hope your birthday celebration was fabulous! Come back and see us again soon~ Lori and the Team at HKWVR

Great week

January 2024
, Springfield, OH United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This property is beautiful inside and out. Amenities were exceptional especially the ice machine on the back deck. A second fridge would be a good addition if possible. Location on Duval is perfect, close enough to walk to multiple attractions but far enough from the hustle and bustle of the crowds.

Manager's Response

An ice machine is super important for cold porch drinks! We're glad you appreciated it.

We hope you'll come and stay with us again ~ soon?

~ Jennifer & Team @ HKWVR

Great Home!

December 2023
, Charlotte, NC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The house was perfect for a large group of various ages and in a great location!

Manager's Response

What a great way to explain Dreaming on Duval ~ we agree! We hope we'll see you all again ~ you now have a vacation home in Key West.

~ Jennifer & Team @ Historic Key West Vacation Rentals

5 Star home

November 2023
, Glen Allen, VA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Dreaming on Duval is a beautiful home with so many special is amazing from top to bottom; front to back...the pool is perfect too!!

Manager's Response

Thank you for noticing the care we put into Dreaming on Duval. We feel it's a great home as well! Please tell us when you'll be back ~ we'll be here!

~ Jennifer & Team @ HKWVR

Absolutely Wonderful

July 2023
, Houston, TX United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

the house is huge and we absolutely loved it. It was so comfortable and right in the heart of things. Would stay here again in a heartbeat.

Manager's Response

Our heart is beating fast waiting for your return to Dreaming on Duval! We love to see happy, familiar guests!

~ Jennifer & Team HKWVR

A wonderful dream!!

June 2023
, Ashburn, VA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Our family had such a great time on our vacation to Key West, and a large part of the experience was staying at this beautiful property! What a dream it was...the bedroom configuration, the large open floor plan on the main level, and the super cute pool were just perfect. We would definitely stay here again and would suggest it to friends and families. Oh, and the location was great too!

Manager's Response

Wow! Thank you kindly for the nice review! We hope you'll all come back and stay with us again, and soon. We love seeing happy, familiar faces.

~ Jennifer & Team HKWVR

Great Vacation!

May 2023
, Palm Harbor, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We stayed at Dreaming on Duval. A beautiful home with plenty of room for our crew of 10 (5 beds & 4.5 baths). The pool and patio were lovely for coffee, swim, or evening leisure. The waterfall was so pleasant to listen to from our room balcony. Location was fantastic. You can walk or golf cart easily to any where in town. The golf cart/scooter rental is right next door and a convenience store right across the street. We had groceries delivered right to the house. All of the info provided from Cindy at the office was awesome with info on what to do and where to go. Jennifer and the entire office was quick with response and made everything easy. Would definitely recommend going through this company.

Manager's Response

Thank you so much for your kind review of Dreaming on Duval as well as the team at HKWVR! We appreciate it and hope to see you again soon! Lori @ HKWVR

Wonderful, Spacious Key West Home on Duval

April 2023
, Briarcliff Manor, NY United States

Overall
5
Cleanliness
5
Location
5
Property condition
5

Fabulous stay! Home was just as pictured, very spacious for a family of 9, well located on the quieter end of Duval but still within walking distance of many bars and restaurants. Historic Key West Vacation Rentals could not have been more efficient and accommodating. Would definitely come back to this home and use Historic Key West Vacation Rentals again! Cindy the concierge was so helpful in setting up almost all of our activities.

Manager's Response

Thank you for taking the time the review Dreaming on Duval. We are so happy that you had a fabulous time~ We can't wait to see you again in sunny Key West! Lori and the HKWVR Team

Amazing time

March 2023
, Kingston, MA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This is the third home we have rented from historic key west and each home was amazing, but this was our favorite. Will Definetly go through historic key rentals for next year.

Manager's Response

We were so happy to see you again (and again!), and can't wait to see you... again!

~ Jennifer & Team HKWVR

Fantastic!!

February 2023
, Lillian, AL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

From booking to checking out was seamless! The home was beautiful and very clean. Couldn't have ask for a better experience.

Manager's Response

We are so happy you enjoyed your time at Dreaming on Duval and hope you're already making plans to come and see us again, and soon!

~ Jennifer & HKWVR team

Excellent home

January 2023
, Grand Rapids, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This home is beautiful with lots of space. Even though it is on Duval Street, it is very quiet. It has a beautiful outdoor space and pool. Historic Key West Vacation Rentals is extremely helpful and responsive. Everything was easy and organized.

Manager's Response

We are so happy you enjoyed your time at Dreaming on Duval! Thank you for taking the time to say such nice things about our home.

~ Jennifer @ HKWVR

Excellent home

January 2023
, San Diego, CA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This home is beautiful with lots of space. Even though it is on Duval Street, it is very quiet. It has a beautiful outdoor space and pool. Historic Key West Vacation Rentals is extremely helpful and responsive. Everything was easy and organized.

Manager's Response

We are so happy you enjoyed your time at Dreaming on Duval! Thank you for taking the time to say such nice things about our home.

~ Jennifer @ HKWVR

Excellent home

January 2023
, San Diego, CA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This home is beautiful with lots of space. Even though it is on Duval Street, it is very quiet. It has a beautiful outdoor space and pool. Historic Key West Vacation Rentals is extremely helpful and responsive. Everything was easy and organized.

Manager's Response

We are so happy you enjoyed your time at Dreaming on Duval! Thank you for taking the time to say such nice things about our home.

~ Jennifer @ HKWVR

Excellent home

January 2023
, Grand Rapids, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This home is beautiful with lots of space. Even though it is on Duval Street, it is very quiet. It has a beautiful outdoor space and pool. Historic Key West Vacation Rentals is extremely helpful and responsive. Everything was easy and organized.

Manager's Response

We are so happy you enjoyed your time at Dreaming on Duval! Thank you for taking the time to say such nice things about our home.

~ Jennifer @ HKWVR

Great Hideaway in Key West

September 2022
, Alanta, GA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Perfect home if your entertaining a large group. Well Appointed, clean and easy to navigate. A great kitchen and dining set up to have a personal chef. Great pool area and cold AC. The mgmt company was exceptional with great communication and support!

Manager's Response

We are so happy you enjoyed your time at Dreaming on Duval ~ and that you got someone to really enjoy that amazing kitchen! We think it's pretty awesome.

Hope you're making plans to come back, and soon!

~ Jennifer @ HKWVR

Fancy Schmancy never felt so good!

April 2022
, San Rafael, CA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The rental agency folks and the property itself were high-end excellent and gracious. Everything touristy in KW is walkable from this house. It's secure...and we even were able to scrunch two cars into the one parking space! Everything about the house is comfortable from the furniture to the linens to the large spaces throughout. Pool was chest deep in the middle, and we could sit all around it on a ledge. We had 11 of us in the house and never felt crowded. The 2 small fridges on the second floor and one on the third floor kept beverages cold when they didn't all fit in the fridge. The privacy of the property allowed nudity without infringing eyes of neighbors. This end of Duval Street is quiet day and night. Plenty of ceiling fans throughout the property allowed us to keep the A/C running on low. The home was insanely CLEAN--what a joy!

Manager's Response

Chris, we are so happy everyone was pleased with Dreaming on Duval & enjoyed their time here. It is a lovely property and has great amenities! Please visit our wonderful little island again when you can.

Cindy & the HKWVR team

Perfect

April 2022
, Point Pleasant Beach, NJ United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Excellent - this booking was from 2 years ago and within that time the home had changed ownership. Smooth transition between rental agencies.

Perfect location - home is quiet even with being on Duval. Concierge coordinated our bike delivery & pick up.

We hooked up at the airport with a taxi for large groups and he was our go to for the entire trip.

The home is beautiful And great for a large group. We were originally to be 12 and last minute 4 were unable to attend. Would say the home is more suited for 10 comfortable in rooms.

Thanks again, Keep Smilin :0)

Manager's Response

We are smilin'! Thank you for taking the time to make such a kind review ~ we appreciate that very much!

Come and see us again, we love this home and are happy to share it with nice happy guests.

~ Jennifer & Team HKWVR

Dreaming until next time...

April 2022
, Glenview, IL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Dreaming on Duval was perfect for our girls getaway! The house is large, yet warm and cozy at the same time. The outdoor space is perfect for lounging around and the pool was great, especially the soothing sound of the waterfall. The front porch was a wonderful place to hang out and people watch. We can't wait to come back!

Manager's Response

We are so happy you enjoyed your time at Dreaming on Duval and we hope you’re already making plans to come and see us again, and soon!

- Jennifer & Team HKWVR

Perfection

March 2022
, Burr Ridge, IL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

A wonderful home in a terrific location.

Manager's Response

We love that you enjoyed Dreaming on Duval ~ we think it's pretty wonderful as well! :) Please come and see us again, and soon! We love seeing happy, familiar faces!

~ Jennifer & Team HKWVR

Family vacation

February 2022
, Forrest City , AR United States

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
5

I have stayed in many homes in Key West and this house was my favorite! Great location to all restaurants and great place to people watch! Kitchen had everything you needed and the pool was awesome. The staff at Historic Key West are great to work with!

Manager's Response

Why thank you! We're so thrilled to be managing Dreaming on Duval and are so glad you enjoyed your family time. Come and stay with us again ~ we love seeing happy, familiar faces!

~ Jennifer & Team HKWVR

Family vacation

February 2022
, Forrest City, AR United States

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
5

I have stayed in many homes in Key West and this house was my favorite! Great location to all restaurants and great place to people watch! Kitchen had everything you needed and the pool was awesome. The staff at Historic Key West are great to work with!

Manager's Response

Why thank you! We're so thrilled to be managing Dreaming on Duval and are so glad you enjoyed your family time. Come and stay with us again ~ we love seeing happy, familiar faces!

~ Jennifer & Team HKWVR

Great House

August 2021
, Little Silver, nj United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The house was in great condition when we arrived and the location is fantastic (just south of all the madness on Duval). Primary bedroom and bathroom were very spacious and the private pool was great to relax in. Would highly recommend for large groups visiting Key West!

Manager's Response

Spencer, thank you very much for your review. This is a great property for a larger group. Everyone has their space! We hope everyone had fun on our little piece of paradise and please come back and visit soon!

Cindy & the HKWVR team

Beautiful Rental!!

July 2021
, Fort Wayne, IN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had an amazing time. A total of 12 guests and we fit comfortably in the house. 2nd floor master was huge! Front porch is right off of Duval which was great for people watching!

Manager's Response

Don't you just love that master bedroom?? And I have to admit, the people watching is totally my favorite. Come and see us again, we're happy you had a good time.

~ Jennifer & Team @ HKWVR