Dreaming on Duval - Nightly Rental

5 Bedrooms

4.5 Bathrooms

10 Guests

5.0

Vacation on historic Duval Street and enjoy complete seclusion in the backyard pool and entertainment area. If you desire large, lush accommodations near the fun as well as peaceful sleep, this 5 BR home with layered impact windows, is perfect for you



About the property

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

  • Type: House
  • Private Pool
  • pets not allowed
  • Outdoor Dining
  • Historic Old Town
  • Monthly: No
  • Nightly & Weekly
  • Air Conditioning
  • Internet Access
  • Kitchen
  • Washer / Dryer
  • Walk in Shower

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Video Tour


5.0 (34 reviews)

5.0

fantastic stay in key west

This is a great house in a great location in Key West.
The house was clean, it was quiet - and the location was fabulous.
The best recommendation we can give is that we would absolutely return to the same place.

Submitted by Long Valley NJ on Mar 23, 2025

5.0

key west

Place was really nice and great location. Management company provided clear instructions and were easy to work with.

Submitted by Brooklyn Park MN on Jan 04, 2025

5.0

great family trip

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!

Submitted by Arlington VA on Dec 02, 2024

5.0

dreaming on duval

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.

Submitted by Kernersville NC on Nov 16, 2024

5.0

absolutely perfect!

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!

Submitted by Richmond TX on Oct 15, 2024

5.0

40th birthday surprise!

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.

Submitted by Glenwood NJ on Oct 03, 2024

5.0

peaceful vacation!!

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.

Submitted by Allen TX on Sep 03, 2024

5.0

awesome!!!!

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!

Submitted by Jeffersonville PA on Aug 19, 2024

5.0

fantastic location and beautiful home

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.

Submitted by Reydon OK on Jul 15, 2024

5.0

great girls getaway

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!

Submitted by Independence Or on Jun 18, 2024

5.0

dreaming on duval

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

Submitted by East Stroudsburg PA on Apr 29, 2024

5.0

family vacation to key west

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

Submitted by Charlottesville VA on Apr 21, 2024

5.0

heaven on duval

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.

Submitted by Niles OH on Apr 08, 2024

5.0

!016 duval was spectacular!

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.

Submitted by Bethesda MD on Mar 09, 2024

5.0

sun in february!

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.

Submitted by Charlottesville VA on Feb 25, 2024

5.0

5 star home

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!!

Submitted by Glen Allen VA on Jan 15, 2024

5.0

great week

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.

Submitted by Springfield OH on Jan 14, 2024

5.0

great home!

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

Submitted by Charlotte NC on Dec 31, 2023

5.0

absolutely wonderful

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.

Submitted by Houston TX on Jul 26, 2023

5.0

a wonderful dream!!

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!

Submitted by Ashburn VA on Jun 30, 2023

5.0

great vacation!

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.

Submitted by Palm Harbor FL on May 13, 2023

5.0

wonderful, spacious key west home on duval

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.

Submitted by Briarcliff Manor NY on May 11, 2023

5.0

amazing time

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.

Submitted by Kingston MA on Apr 02, 2023

5.0

dreaming on duval

Overall, we enjoyed our stay.

Submitted by New Hope PA on Mar 28, 2023

5.0

fantastic!!

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

Submitted by Lillian AL on Mar 16, 2023

5.0

excellent home

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.

Submitted by San Diego CA on Jan 24, 2023

5.0

great hideaway in key west

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!

Submitted by Alanta GA on Sep 26, 2022

5.0

fancy schmancy never felt so good!

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!

Submitted by San Rafael CA on May 19, 2022

5.0

dreaming until next time...

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!

Submitted by Glenview IL on Apr 25, 2022

5.0

perfect

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)

Submitted by Point Pleasant Beach NJ on Apr 25, 2022

5.0

perfection

A wonderful home in a terrific location.

Submitted by Burr Ridge IL on Mar 29, 2022

5.0

family vacation

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!

Submitted by Forrest City AR on Feb 20, 2022

5.0

great house

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!

Submitted by Little Silver nj on Aug 12, 2021

5.0

beautiful rental!!

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!��

Submitted by Fort Wayne IN on Jul 24, 2021

Location

May 14-14, 2025
Reserve
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