Entire home

~DREAMING ON DUVAL~ 5 bedroom, 4.5 bath home with private pool and parking

Photo gallery for ~DREAMING ON DUVAL~ 5 bedroom, 4.5 bath home with private pool and parking

A spacious dining area with a long wooden table, wicker chairs, and a central bowl of items.
A swimming pool with a tiled edge, surrounded by lush greenery and a wooden deck with lounge chairs.
A modern kitchen with a gas stove, white cabinetry, and a dining area with wicker chairs and a wooden table.
A covered porch with wicker furniture and a view of nearby buildings.
A modern kitchen with white cabinetry, a granite countertop, and a stainless steel refrigerator.

Reviews

10 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • Private garden
    A rare find — relax in the peaceful, private garden space.
  • Discover nearby landmarks
    Near Duval Street

Popular amenities

  • Balcony
  • Private pool
  • Gas barbecue
  • Air-conditioning
  • Refrigerator
  • Washing machine

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪1 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪1 min walk‬
  • Place, South Beach
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪10 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Single Beds

Bedroom 4

2 Single Beds

Bedroom 5

1 King Bed

4 bathrooms, 1 half bathroom

Bathroom 1

Bathtub · Toilet · Shower only · Jetted bathtub

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet

Bathroom 5

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden
Dining area

Add dates for prices

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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. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
View more Holiday homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Duval Street - 1 min walk - 0.0 km
  • 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
  • ‪Moondog Cafe & Bakery - ‬4 min walk
  • ‪Cuban Coffee Queen (Duval) - ‬2 min walk
  • ‪801 Bourbon Bar - ‬3 min walk
  • ‪Old Town Tavern - ‬2 min walk

Frequently asked questions

Does ~DREAMING ON DUVAL~ 5 bedroom, 4.5 bath home with private pool and 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~ 5 bedroom, 4.5 bath home with private pool and parking?

As of 26 Oct 2026, prices found for a 1-night stay for 2 adults at ~DREAMING ON DUVAL~ 5 bedroom, 4.5 bath home with private pool and parking on 8 Dec 2026 start from £6,769, 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~ 5 bedroom, 4.5 bath home with private pool and parking pet-friendly?

No, pets are not allowed at this property.

How much is parking at ~DREAMING ON DUVAL~ 5 bedroom, 4.5 bath home with private pool and parking?

On-site parking is available at the property.

What time is check-in at ~DREAMING ON DUVAL~ 5 bedroom, 4.5 bath home with private pool and parking?

Check-in begins at 4:00 PM.

What time is check-out at ~DREAMING ON DUVAL~ 5 bedroom, 4.5 bath home with private pool and parking?

Checkout is at 10:00 AM.

Where is ~DREAMING ON DUVAL~ 5 bedroom, 4.5 bath home with private pool and 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 70 out of 73 reviews
Rating 8 - Good. 2 out of 73 reviews
Rating 6 - Okay. 0 out of 73 reviews
Rating 4 - Poor. 1 out of 73 reviews
Rating 2 - Terrible. 0 out of 73 reviews

10/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house, location, would rent it again
Stayed 4 nights in Jun 2026
Response from VrboOwner on 17 Jul 2026
What a nice review and we hope you'll be coming back sooner than later! Thank you! ~ The Team @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Dreaming on Duval was absolutely fantastic! The house is beautiful, spacious, and incredibly well-appointed—and honestly, even better than the pictures!The location is perfect—at the quieter end of Key West, but still just a short walk to all the action. The back patio and pool area were ideal for an afternoon dip and pre-dinner cocktails. The house had plenty of space for our party of 8 adults, with large, comfortable bedrooms and room for everyone to spread out.Our only (very minor!) complaint? We somehow managed to survive the entire stay without Kleenex in the bedrooms. We couldn’t recommend Dreaming on Duval more and would absolutely stay here again!
Stayed 4 nights in Sep 2026
Response from VrboOwner on 25 Oct 2026
Thank you for the kind and honest review of Dreaming on Duval! We hope you'll come and stay with us again, and soon! We don't usually supply Kleenex but I will recommend that. ~ The Team @ Historic Key West Vacation Rentals
From a partner site

10/10 Excellent

60th bday celebration

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: the house was nice and enough amenities. Ice maker outside was a bonus. Pool needed a Chiller. the upstairs AC makes a gurgling noise several times a night making it difficult to sleep. i would have liked to have known that there were sofa sleepers before arrival, i did not see that info. anywhere on the rental sight. other than that, the house was a GEM! we had a fantastic time and the rental company is great!
Response from VrboOwner on 30 Sept 2026
Thank you for the kind and honest review of your stay at Dreaming on Duval. We're thrilled you ended up enjoying your stay with us and we hope you'll come and stay with us again. Please remember we're always here to address any issues during your stay. ~ The Team @ HKWVR
From a partner site

10/10 Excellent

Amazing!

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: Very amazing house that suited our family of 7 perfect
Response from VrboOwner on 5 Aug 2026
Thank you, Joshua, for taking time to review your stay at Dreaming on Duval. We agree that it is an amazing house!! We hope to see you again in the future in sunny Key West! The Team at HKWVR
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing trip!
Stayed 6 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful place . Great location We’re coming back next year
Stayed 7 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great spot in downtown Key West!
Stayed 5 nights in Mar 2026
Response from VrboOwner on 18 Apr 2026
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family stay to honor our parents who recently passed. With two families/3 kids 26-15 there was a perfect amount of space to be alone or to gather together around the pool. All the amenities of home and then some. Check in/check out couldn’t be easier. Location can’t be beat. We rented two golf carts and had private parking for them. We WILL be back!
Stayed 4 nights in May 2026
Response from VrboOwner on 11 Jun 2026
We are so sorry for your loss and send you and your family strength and hopes to find joy. We look forward to your next stay, and hope it will be with good memories. ~ The Team @ Historic Key West Vacation Rentals
From a partner site

10/10 Excellent

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
Response from VrboOwner on 12 Apr 2026
That is so nice to hear! Thank you for the kind review! ~ The Team @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Mar 2026
Response from VrboOwner on 17 Apr 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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great family vacation

Perfect location, great house for families.
Stayed 9 nights in Dec 2022
Response from VrboOwner on 30 Dec 2022
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location!

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!
Stayed 8 nights in Mar 2024
Response from VrboOwner on 23 Apr 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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great trip.

Everything was great, and the place was beautiful.
Stayed 6 nights in Apr 2023
Response from VrboOwner on 24 Apr 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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay on Duval

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!
Stayed 5 nights in Mar 2025
Response from VrboOwner on 10 Apr 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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved it!

This is a very nice house with a cute little pool in a good location.
Stayed 5 nights in Mar 2025
Response from VrboOwner on 10 Apr 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
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location and private

It was a great location and was a very private setting for being right in the center of key west. Fun trip
Stayed 4 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location and first class accommodations

We had a great week there- work and family time. The pool was a big hit with the children.
Stayed 5 nights in Feb 2025
Response from VrboOwner on 19 Feb 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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely breathtaking!

You really can ask for a better place or a better location! You won’t be disappointed!
Stayed 4 nights in Feb 2025
Response from VrboOwner on 21 Feb 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
From a partner site

10/10 Excellent

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.
Response from VrboOwner on 27 Aug 2025
We are looking forward to your next stay! Come and bring family and friends! The Team @ HKWVR
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location and house

The property is very central and the house is really nice and clean. Communication was great and easy.
Stayed 4 nights in Sep 2024
Response from VrboOwner on 23 Sept 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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friends turn 60

Loved the heated pool and comfortable beds. Great location and porch overlooking Duval St.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friends Get Away

Very easy and the place was great!
Stayed 7 nights in Dec 2022
Response from VrboOwner on 17 Dec 2022
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Dreaming On Duval

This house was beautiful and the perfect location! We had a blast and can't wait to book again!!!
Stayed 4 nights in Jan 2022
Response from VrboOwner on 6 Feb 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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect getaway

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.
Stayed 6 nights in Dec 2024
Response from VrboOwner on 10 Jan 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
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