~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
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***
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
About the area
Key West
Located by the sea, this holiday home is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Key West Butterfly and Nature Conservatory and MLK Community Pool & Community Center are also worth visiting.
Ernest Hemingway Home and Museum - 1 min walk - 0.2 km
Key West Lighthouse and Keeper's Quarters Museum - 1 min walk - 0.2 km
South Beach - 8 min walk - 0.7 km
Southernmost Point - 9 min walk - 0.8 km
Getting around
Key West, FL (EYW-Key West Intl.) - 9 min drive
Restaurants
Circle K - 1 min walk
Old Town Tavern - 2 min walk
Moondog Cafe & Bakery - 4 min walk
Cuban Coffee Queen (Duval) - 2 min walk
Rum Bar at the Speakeasy Inn - 2 min walk
Frequently asked questions
Does ~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at ~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking?
As of 8 May 2026, prices found for a 1-night stay for 2 adults at ~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking on 17 May 2026 start from NZ$3,244, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is ~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking pet-friendly?
No, pets are not allowed at this property.
How much is parking at ~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking?
On-site parking is available at the property.
What time is check-in at ~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking?
Check-in begins at 4:00 PM.
What time is check-out at ~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking?
Checkout is at 10:00 AM.
Where is ~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking located?
Located in Old Town Key West, this holiday home is steps away from Tennessee Williams Key West Exhibit, Duval Street and Ernest Hemingway Home and Museum. Florida Keys Beaches and South Beach are also within 10 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Thank you for the kind review of Dreaming on Duval! We hope you'll come and stay with us again, and soon.
~ The Team @ Historic Key West Vacation Rentals
We had an awesome time. The Managment company went above and beyond to make our stay excellent. Can't say enough good things about them and would highly recommend them and this property.
Mike K.
Stayed 4 nights in Apr 2026
Response from VrboOwner on 4 May 2026
Thank you so much for the kind review of Dreaming on Duval and us as well! We hope you're making plans to come and stay with us again, and soon!
~ The Team @ Historic Key West Vacation Rentals
From a partner site
10/10 Excellent
David H.
31 March 2026
Dreaming in Duval Lived up to its hype
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I do not recommend this vacation rental.
Reviewer Comments:
Great experience in Duval because of where we stayed
David H.
Response from VrboOwner on 12 April 2026
That is so nice to hear! Thank you for the kind review!
~ The Team @ Historic Key West Vacation Rentals
This house was beautiful, immaculate, and the rental agency was incredibly helpful. My kids loved the pool, dining on the deck was so lovely, the bedrooms were beautiful. Private decks off the back were a treat and really made it special. I was concerned about the location, but now I’m not sure why??? it was such a great spot- you can walk down to the southernmost point and beach, access to shops and restaurants! Easy bike ride to everywhere. The only con of our trip had nothing to do with our rental house- there don’t seem to be a lot of little markets with fresh produce in Key West so we had to order everything from Publix online.
Cornelia T.
Stayed 7 nights in Mar 2026
Response from VrboOwner on 17 April 2026
Thank you for the kind and honest review of Dreaming on Duval ~ and for the tips for future renters. We hope you'll bring the family back to make some more memories with us soon!
~ The Team @ Historic Key West Vacation Rentals
From a partner site
10/10 Excellent
Adam G.
26 August 2025
Great location, five star stay
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Large key west home on main drag with pool and amenities for any and all occasions. Good for family, friends and all the above. Will be renting again.
Adam G.
Response from VrboOwner on 27 August 2025
We are looking forward to your next stay! Come and bring family and friends!
The Team @ HKWVR
We just completed a great stay at his property.It was extremely clean, the nights were quiet (even over St. Patricks Day and Spring Break).Fantastic location - we left the car in the dedicated spot and walked everywhere.Best recommendation we can give is that we would absolutely book here again!
Steve G.
Stayed 5 nights in Mar 2025
Response from VrboOwner on 10 April 2025
We are thrilled to hear you enjoyed your time at Dreaming on Duval! We can't wait for you to come back again.
If you want to get around the island a little 'faster' ~ get a bike. Our concierge is happy to help (no extra cost to you).
~ Jennifer & Team @ Historic Key West Vacation Rentals
This is a very nice house with a cute little pool in a good location.
Kimbrough T.
Stayed 5 nights in Mar 2025
Response from VrboOwner on 10 April 2025
We are so happy you enjoyed your time at Dreaming on Duval. We hope you'll make it back to Key West to spend some more time with us, soon!
~ Jennifer & Team @ Historic Key West Vacation Rentals
Barbara, thank you for the review. It is a lovely larger home perfect for10 people! The pool and parking are also nice additions. We are happy you enjoyed your time here and please visit our great little island again!
Cindy & the HKWVR team
From a partner site
10/10 Excellent
Zeke F.
5 August 2025
Awesome Experience!
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
House was great. Tons of space for the whole family. It is close to everything! Pool is awesome and cooled us off great!! Rental company was great as well. House is well kept and really clean! Thank you will be back soon!!
Zeke F.
Response from VrboOwner on 8 August 2025
Your trip sounds wonderful and we hope you'll come and make some more memories with us!
~ The Team @ HKWVR
We had a great week there- work and family time. The pool was a big hit with the children.
Lewis W.
Stayed 5 nights in Feb 2025
Response from VrboOwner on 19 February 2025
Thank you so much for the kind review of Dreaming on Duval ~ we hope you'll come and stay with us again!
~ Jennifer & Team @ Historic Key West Vacation Rentals
My family really enjoyed this property!! Great location, house and even though it is located on Duvall Street, we hung out in the backyard and it was very quiet!
Daren S.
Stayed 8 nights in Mar 2024
Response from VrboOwner on 23 April 2024
That is a great way to review Dreaming on Duval! It is a great home in a great location ~ you're super close to everything but the backyard makes you feel like you're in your own private home.
~ Jennifer & Team @ Historic Key West Vacation Rentals
You really can ask for a better place or a better location! You won’t be disappointed!
Stacey D.
Stayed 4 nights in Feb 2025
Response from VrboOwner on 21 February 2025
Thank you for the super kind review of Dreaming on Duval! We hope you're already making plans to come and stay with us again!
~ Jennifer & Team @ Historic Key West Vacation Rentals
Everything was great, and the place was beautiful.
DEBBIE B.
Stayed 6 nights in Apr 2023
Response from VrboOwner on 24 April 2023
Thank you for taking the time to review Dreaming on Duval and we are thrilled you had a good time in Key West!
Hope you'll come and see us again and soon!
~ Jennifer & Team Historic Key West Vacation Rentals
The property is very central and the house is really nice and clean. Communication was great and easy.
Kenneth W.
Stayed 4 nights in Sep 2024
Response from VrboOwner on 23 September 2024
Thank you for the kind review of Dreaming on Duval! We hope you'll come and make some more memories with us!
~ Jennifer & Team @ Historic Key West Vacation Rentals
Fabulous location in the heart of Key West. Easy access to property and amenities. Clean, well-equipped and comfortable house for our crew of teens and adults. Highly recommend.
Verified traveller
Stayed 6 nights in Dec 2024
Response from VrboOwner on 10 January 2025
We hope you're already making your way back to Key West to stay with us again!
~ Jennifer & Team @ Historic Key West Vacation Rentals
Loved the heated pool and comfortable beds. Great location and porch overlooking Duval St.
Lisa G.
Stayed 4 nights in May 2024
Response from VrboOwner on 14 May 2024
Thank you for the kind review of Dreaming on Duval! We hope you're already making plans to come back and make some more memories!
~ Jennifer & Team @ Historic Key West Vacation Rentals
From a partner site
10/10 Excellent
Chris O.
4 January 2025
Key West
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Place was really nice and great location. Management company provided clear instructions and were easy to work with.
Chris O.
Response from VrboOwner on 5 January 2025
That is so nice to hear! We hope you'll come and enjoy some more Key West time with us again, and soon!
~ Jennifer & Team @ Historic Key West Vacation Rentals
What kind words for Dreaming on Duval! We hope to make it easy every time you come and stay with us. :)
~ Jennifer @ Historic Key West Vacation Rentals
This house was beautiful and the perfect location! We had a blast and can't wait to book again!!!
Erika W.
Stayed 4 nights in Jan 2022
Response from VrboOwner on 6 February 2022
Erika, Thank you for reviewing Dreaming on Duval. It is a lovely property and has plenty of room for a larger party of 10. We look forward to seeing you again in Key West where you can have plenty of fun and relax!
Cindy & the HKWVR team
This house is great for a group. It is clean and well set up. The location is perfect and convenient to everything we wanted to do on our vacation.
I would recommend this house to anyone traveling down to Key West.
Melanie O.
Stayed 5 nights in Nov 2023
Response from VrboOwner on 6 December 2023
We hope these guests are already making plans to come back and see us again! Dreaming on Duval is a great home for larger groups (10 people) in an amazing location so everyone can find something fun to do.
~ Jennifer @ Historic Key West Vacation Rentals
That's so nice to hear! We hope you're already making plans to come and see us again!
~ Jennifer & Team @ Historic Key West Vacation Rentals
From a partner site
10/10 Excellent
Elizabeth P.
17 November 2024
Dreaming on Duval
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
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.
Elizabeth P.
Response from VrboOwner on 23 November 2024
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
From a partner site
10/10 Excellent
Elizabeth P.
16 November 2024
Dreaming on Duval
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
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.
Elizabeth P.
Response from VrboOwner on 12 December 2024
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
Thank you so much for the kind review of Dreaming on Duval! We hope you're already making plans to come and stay with us again.
~ Jennifer & Team @ Historic Key West Vacation Rentals
About the host
Hosted by Historic Key West Vacation Rentals
Languages:
English
Premier Host
They consistently provide great experiences for their guests