Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16

Photo gallery for Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16

A pool area with a wooden deck, a covered seating area, and a white building with glass doors.
A white two-story house with a balcony, a white picket fence, and a brick pathway.
A covered porch with green chairs and a table, surrounded by lush tropical plants.
A narrow brick pathway flanked by a white picket fence and lush greenery, leading to a white colonial-style building with balconies.
A wooden cabin bedroom with two beds, a ceiling fan, and a large window with curtains.

Reviews

9.4 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Private garden
    A rare find — relax in the peaceful, private garden space.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Duval Street

Popular amenities

  • Balcony
  • Private pool
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Washing machine

Explore the area

View map
Key West, FL
  • Place, Key West Cemetery
    ‪6 min walk‬
  • Place, Duval Street
    ‪8 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪15 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪10 min drive‬

Rooms & beds

7 bedrooms (sleeps 16)

Bedroom 1

1 Single Murphy Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

1 King Bed

Bedroom 5

1 King Bed

Bedroom 6

1 King Bed

Bedroom 7

2 Double Beds

5 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Bathroom 5

Bathroom 6

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 in Key West, this holiday home is in the city centre. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting. Power boating and swimming offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours nearby.
View more Holiday homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Key West Cemetery - 6 min walk - 0.6 km
  • Duval Street - 8 min walk - 0.7 km
  • Mallory Square - 13 min walk - 1.2 km
  • Harry S. Truman Little White House - 14 min walk - 1.2 km
  • Ernest Hemingway Home and Museum - 15 min walk - 1.3 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 12 min drive

Restaurants

  • ‪Kermit's Key West Key Lime Shoppe - ‬8 min walk
  • ‪Cuban Coffee Queen Waterfront - ‬5 min walk
  • ‪Schooner Wharf Bar - ‬7 min walk
  • ‪Margaritaville - ‬7 min walk
  • ‪Half Shell Raw Bar - ‬6 min walk

Frequently asked questions

Does Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16 have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16?

As of 3 November 2026, prices found for a 1-night stay for 2 adults at Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16 on 13 December 2026 start from NZ$12,547, 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 Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16 pet-friendly?

No, pets are not allowed at this property.

How much is parking at Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16?

On-site parking is available at the property.

What time is check-in at Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16?

Check-in begins at 4:00 PM.

What time is check-out at Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16?

Checkout is at 10:00 AM.

Where is Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16 located?

Located in Old Town Key West, this holiday home is within a 10-minute walk of The Kite House and Duval Street. Florida Keys Beaches and Mallory Square are also within 15 minutes.

Reviews

9.4

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. 31 out of 41 reviews
Rating 8 - Good. 8 out of 41 reviews
Rating 6 - Okay. 1 out of 41 reviews
Rating 4 - Poor. 0 out of 41 reviews
Rating 2 - Terrible. 1 out of 41 reviews

9.8/10

Cleanliness

10/10

Property conditions & facilities

9.8/10

Check-in

10/10

Communication

9.6/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
1
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome historic home. The patio and pool are beautiful. Perfect for our group of 8.
Stayed 3 nights in Feb 2026
Response from VrboOwner on 11 March 2026
Thank you for sharing your experience!We’re so glad you had a great stay! It would be our pleasure to host you again anytime!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Check in was easy and the host was very accommodating. Spacious home and convenient location. The kids loved the pool.
Stayed 5 nights in Dec 2025
Response from VrboOwner on 6 January 2026
Thank you for sharing your experience! We’re glad the location and home suited your family, and that everyone enjoyed the pool. We look foward to hosting you again.
Verified review

10/10 Excellent

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

Great place

Great place. Good location and plenty of rooms.
Stayed 3 nights in Nov 2019
Response from VrboOwner on 2 December 2024
Thank you for your review and for choosing our Classic Key West Estate for your vacation! It was a pleasure hosting you and we hope to have the chance again sometime soon. Best, VHKW
Verified review

10/10 Excellent

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

great central location

the house was great for our large group and so close to the heart of key west!
Stayed 5 nights in Aug 2020
Response from VrboOwner on 15 December 2021
Hi Shantell, We are so grateful for the 5 star review! Hope to see you again and that you have a happy holiday season!
Verified review

10/10 Excellent

Liked: Cleanliness, property conditions & facilities, communication
Lovely home with that key west flair. Beautiful architecture
Stayed 5 nights in Jul 2025
Verified review

10/10 Excellent

relaxing

my family and i loved staying in this historic house. there were three generations staying and we all found it comfortable, relaxing and trully centrally located.
Stayed 3 nights in Aug 2018
Response from VrboOwner on 19 December 2024
We're thrilled to hear all generations enjoyed our Classic Key West Estate! Thank you for staying with us and for taking the time to share your experience, Virginia. We would love to host you and your group anytime you're back in town! Best, VHKW
Verified review

10/10 Excellent

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

Paradise

The property was paradise and perfect for our group of 13. Audrey was awesome and helpful before and during our stay! Would love to come back to this property
Stayed 4 nights in Apr 2025
Response from VrboOwner on 8 January 2026
Hello Karen,Paradise indeed! We’re so glad the property worked well for your group and that Audrey made your stay easier. We’d love to welcome you back for another getaway soon!
Verified review

10/10 Excellent

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

Comfortable Stay

Great Location and accommodations. Provided list of maintenance items to property manager.
Stayed 7 nights in Nov 2022
Response from VrboOwner on 16 December 2024
Thank you so much for staying with us and for your thoughtful feedback, Thomas! It was a pleasure hosting you for your time in Key West. Best, VHKW
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
10/10 for this property! I stayed here with my siblings, all of our kids, and our mom for my dad’s celebration of life. The house was even better than the pictures, and there was plenty of space for all of us. The location is perfect—just a 5-minute walk to Half Shell, Schooner’s, and Alonzo’s, all of my family’s favorite spots. I highly recommend this place to anyone traveling with a large group and/or kids.
Stayed 5 nights in Sep 2025
Response from VrboOwner on 7 January 2026
Hello J. Joelle.Thank you for sharing your experience. We’re so glad the house worked well for your family and provided a comfortable space for your dad’s celebration of life. It means a lot that you enjoyed the location and felt at home. We’d be happy to welcome you back for another memorable stay.
Verified review

8/10 Good

Spacious and excellent location

Loved the pool. All kings a plus. Great for a large group.
Stayed 7 nights in Mar 2019
Response from VrboOwner on 13 January 2025
Thank you for your wonderful review and for spending your Key West getaway with us, Pamela! It was a pleasure hosting you and we hope to have the chance again sometime soon. Best, VHKW
Verified review

10/10 Excellent

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

Great for group party

Clean and comfortable classic Key West mansion. Great for a group of couples who all want a separate bedroom.
Stayed 4 nights in Dec 2023
Response from VrboOwner on 14 December 2023
Nick, Thank you for the great review! We look forward to seeing you again soon.
Verified review

10/10 Excellent

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

Fabulous for friends getaway

We rented this house for a friends getaway (8 adults and 3 kids). Perfect house for a large group. Thoroughly enjoyed the pool. Highly recommend!
Stayed 5 nights in Jul 2024
Response from VrboOwner on 2 December 2024
We're thrilled to hear our home was a the perfect base for your group of 11! Thank you for your kind review and for choosing to stay with Vacation Homes of Key West. If you ever find yourself back in the area, we would love the chance to host you again! Best, VHKW
Verified review

10/10 Excellent

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

Great place for a large group

We were celebrating grandchildren high school graduations with our whole family. This house was a perfect fit for our 10 adults and 2 children. Lots of bedrooms and bathrooms, big kitchen, nice size pool in the shade. We enjoyed our time sitting around the living room chatting and laughing together. Convenient location to dining, entertainment, parking and points of interest. Loved the history of the house.
Stayed 7 nights in May 2025
Response from VrboOwner on 8 January 2026
Hello Donna,We’re so glad the house worked perfectly for your family celebration! Thank you for your kind words.We’d love to host you again.
Verified review

10/10 Excellent

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

Excellent Location, Beautiful Home

Beautiful home. Our group of 14 adults and 2 babies stayed comfortably in this very large home. The pool was clean and warm. Walking distance to pretty much everywhere. Highly recommend.
Stayed 7 nights in Dec 2019
Response from VrboOwner on 18 December 2024
We're thrilled to hear your group made the most of all our Classic Key West Estate has to offer during your stay with us! Thank you for taking the time to review your experience for all of our future guests. Best, VHKW
Verified review

10/10 Excellent

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

Great Family Stay at this Key West Estate

What a wonderful historic home in the heart of Key West. We had 14 family members stay together in this 6 bedroom home with ensuites in most of the bedrooms which gave couples needed privacy. We loved the home and enjoyed our mornings and evenings on the expansive porch. Only a few blocks from the Marina/Harbor, Duval street, Simonton Street Beach, and a market. Highly recommend this beautiful home.
Stayed 7 nights in Feb 2024
Response from VrboOwner on 26 February 2024
Thank you so much, Joanne! We sincerely appreciate you taking the time to leave us such a great review and are thrilled to hear that you enjoyed the home and your stay with us in Key West. We hope to see you again in the future. VHKW
Verified review

10/10 Excellent

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

Key West getaway

This property is exactly what it looks like according to the website. It is absolutely historically gorgeous. Walking distance to almost everything. No real problems at all except for leaves in pool, however it was cleaned twice while we were there. Hope to stay at this location again.
Stayed 4 nights in Apr 2022
Response from VrboOwner on 19 December 2024
We're thrilled to hear you loved the historic character and all the amenities our estate has to offer! Thank you for staying with us and for taking the time to share your experience. We hope to have the opportunity to host you again the next time you're in Key West! Best, VHKW
Verified review

8/10 Good

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

Brilliant stay in Key West

A lovely expansive home with old world charm. Enjoy the best of old town Key West. The home is well appointed with great furnishings, space for the entire family to explore Key West's finest. The beds are comfortable, showers are lovely with plenty of hot water. Historical figures frequented the home in the past making it an even richer experieince for the history buffs in our group. We enjoyed renting the entire estate incluidng the cottage which added space and ambiance including the outdoor shower and dual bathtubs. The meditation room was greatly appreciated. VHKW was helpful during the trip and was readily available to fix issues.
Stayed 7 nights in May 2024
Response from VrboOwner on 1 July 2024
Thank you so much for the great review, Holly. We are so glad to hear you enjoyed your stay, the home, and that we were able to resolve any issues quickly and to your liking. We hope to see you again in the future. VHKW
Verified review

10/10 Excellent

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

Amazing property!

We had a group of 10, so finding a place big enough for everyone can be a challenge. This house is perfect. Great location and walking distance to some great restaurants and most of the main attractions in Key West. The house has a well-stocked kitchen, and the pool in the back is a great place to hang out with friends. We had to call the management company a few times (once for an internet issue, and another time when there was an issue with the door lock for the apartment next to the pool). Both issues were addressed quickly. The only downfall was we had to leave when our vacation ended!
Stayed 6 nights in Feb 2021
Response from VrboOwner on 13 January 2025
We're so happy you your group were able to spread out and settle in at our Key West Estate! It was a pleasure hosting you all and helping with anything needed during your stay. We would love the chance to host you all again anytime you find yourselves back in town! Best. VHKW
Verified review

6/10 Okay

Liked: Cleanliness, check-in, location
Disliked: Listing accuracy

Cool old house, but…..

This house was located within walking distance to almost everything which was a plus and the kids loved the pool. Some problems we encountered were having no hot water everyday at some point and having to go out and flip the breaker (which apparently is on the same circuit as the pool) sometimes more than once a day. We had no internet for 2 days which I could overlook, but not the hot water situation. Also, letting folks with young children know that next door is a clothing optional men’s resort would be helpful.
Stayed 5 nights in Nov 2024
Response from VrboOwner on 2 December 2024
Hi Debbie, Thank you for the feedback. We are glad that you enjoyed the location of the property and the pool. We apologize for the trouble with the breaker. Before your stay an electrician inspected everything and said it had been fixed but that is clearly not the case, so thank you for bringing it to our attention. We will be sure to send someone out there again ASAP. We're glad that we were able to repair your internet, though, so you had it for the majority of your stay. The property is located next to a men's resort, but the landscaping, buildings, and fences should provide plenty of privacy. - VHKW
Verified review

10/10 Excellent

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

Swimming and Location

Lots of sleeping options and walkable for the most point. House rules were not onerous and porches were a good place to just sit and relax. I do wish we could have used the parking permit for our golf carts. As non residents, we had a bit of difficulty finding non permitted parking. Many times the resident permit spot right in front of the house was unoccupied. Be aware that checkout and luggage storage caused some juggling. Checkout at 10 a.m. and flights at 2 and 4 in the afternoon and no place to put luggage without paying even more for some portage company. How about a place right inside the gate or on the front porch for an hour or two? Plenty of plates and towels and games. The kids were in the pool morning, noon and night. Just the right size for the youngest up to 11. All in all though this was a great place for all of our kuds and grandchildren to help us celebrate our 50th anniversary.
Stayed 5 nights in Aug 2023
Response from VrboOwner on 16 January 2025
Thank you so much for choosing our estate as the home base for the 50th anniversary celebrations! We're thrilled to hear your family was able to settle in and spread out, making our house your own. It was an honor hosting you all and we look forward to welcoming you back anytime you return to town! Best, VHKW
Verified review

8/10 Good

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

Great Vacation

Our honest review from a party of nine. This house was our first real vacation since covid. We were looking forward to spending time with family and friends. Location: great location near everything. Only a quick walk or Uber to what we wanted to do. House: great house. The house is really nice and was well appointed. The pool in the back (while not large) is great for unwinding. The house was super clean and there were plenty of towels, soap, toilet paper to get us started. The management company recommended keeping counter clean - which was good advice and ants are prevalent in a beach town! Management Company/Owner: The management company was very responsive to us and we are planning to use them again. We did have an issue with a deck being built next to our and our 5 year old’s bedrooms. Unfortunately construction started at 7:30 AM and went on thorough out the entire day. After the third day of being woken up, we called the management company. They weren’t aware of the construction and really went out of their way to help us. The owner later informed the management company that the work was permitted - a point that would have made a material difference in whether we rented the property if we had known. The management company did get the owners of the house to cease working outside. For that - you should feel comfortable with VHKW. They were terrific.
Stayed 7 nights in Aug 2021
Response from VrboOwner on 28 September 2021
Hello Adam, We appreciate you taking the time to share your experience! Thank you for giving VHKW the opportunity to assist you with planning a much needed vacation during such stressful and challenging times! We apologize for any inconvenience caused by the construction next door, but we are happy that we were able to arrange for the work to be done at another time. It’s wonderful to hear that you enjoyed the property and your overall stay! We would love to welcome you back sometime in the near future! VHKW Tram
Archival

2/10 Terrible

Are you kidding me???

Well at first glance this "HGTV" home is lovely....however after being gone for the day at lunch and sightseeing, getting back to the home full of termites is anything but spectacular. Termites in our beds, crawling in our clothes we had put away, crawling in our children's diapers and toys, all over pillows and lamps. When attempting to contact the rental company, there is not a specific 24 hour number. Instead, you call the number and are given instructions for after hours emergencies. Apparently, this company does not value customer service as we called several times FOUR HOURS ago and left several messages. This is unacceptable and really unbelievable that someone would see this property as fit to rent. There is NO WAY that this problem just started today. The patchwork and rotted placed in the floor are throught the house. The amount of time spent to plan this trip for 10 adults and 3 children is so disappointing. My aunt put this trip together as a final farewell to her husband she lost last year. The two of them traveled to Key West for over twenty years and loved it so much and had so many wonderful memories that she wanted to share with us.
Response from VrboOwner on 26 March 2020
We are really sorry this guest's stay was interrupted by termites swarms. Termites are everywhere in Key West and unfortunately it can not be predicted when they will come out swarming. Even though it is unpleasant to have flying bugs around - they are absolutely harmless. The guest called late at night on Saturday and their call was returned on Sunday morning. They were relocated the same day as termites normally swarm for a couple of days. The house was treated for termites afterwards. In 2015 the home received a major make over - floors were refinished, decks repaired and painted, interior painted, all mattresses and bedding replaced, new furniture and more. We hope our future guests enjoy this classic home!
Verified review

8/10 Good

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

Nice stay in Key West

We had 9 family members staying for a week, aged 18-80. There was plenty of room to spread out and the location was convenient. The house has all the characteristics you'd expect in a 100 year old historic house. Very charming, but a few little quirks. Due to Covid, we ate in for each meal and did a lot of cooking. The kitchen was pretty well stocked (except we could have used more silverware, there was just enough to go around for each meal). As expected with an older house, some of the doors did not close properly or completely. The rear cottage could not be locked from the outside when we arrived, but maintenance came that same evening to install a new lock and also to adjust an exterior door on the main house. The upstairs hall bathroom's shower door doesn't close fully so the water is leaking out onto the floor when you take a shower ( and running down the interior wall to the bathroom below). So it could use some maintenance. The front porch is a great place to hang out for some quiet time with a book and have your morning coffee. Plus, to start happy hour in the evening. The back patio area was also a favorite hangout spot with a dining room table, outdoor TV and the pool. The house was well stocked with both pool towels and bath towels, plus there's a washer and dryer available there. The rental came with a parking pass to the local garage, although we were able to find street parking very close by each day, so we never had to use it. We would definitely stay here again and recommend this property! It's perfect for a large group of people. And Bella, our contact for the property was also great, very accessible and responsive to all our questions and needs! Thanks Bella!
Stayed 7 nights in Jul 2020
Response from VrboOwner on 2 October 2020
Thank you for taking the time to share your experience! We are thrilled that you enjoyed your stay at Classic Key West Estate and found it comfortable and well stocked. This is an old historic home and thank you for appreciating it for what it is! :) We are addressing the items you pointed out with maintenance including the silverware, door lock and shower, thank you for bringing these to our attention! We look forward to having you again in the near future! VHKW Team
Verified review

8/10 Good

Loved it !!!!

We had 5 couples stay here together and we all loved it. Great location. On a side note, please don't take this as a slam, because the house was "AWESOME", but a few things need fixing. Probably take a day and maybe $500.00 to fix. One of the ironing boards is broken. Won't stand up. The bedside lamp in the Anne's room doesn't work. The switch doesn't work. We had to screw and unscrew the light bulb. One of the exterior shutters flaps in the wind at night. It's on the upstairs bedroom on the NW corner of the house. It needs an eye hook to fix it. The upstairs hall bath need a lot of TLC - door know is broken, the shower doors don't meet so water pours out on the floor, the toilet seat isn't fastened to the toilet so it slides around when you sit on it. There is no vent to take the heat and moisture out so it gets terribly hot and humid after a shower. A couple of outlet covers are missing in the pool cottage. There's a floor register missing in the downstairs hall bath. We almost lost an iphone down the vent when one of the girls dropped her phone. The WiFi is confusing, the directions at the house are not correct. We called the number for help and they gave us the correct user ID and password. I know that this might sound picky, but if no one says anything, it doesn't get fixed. Again, over all, we loved the this house and would stay there again.
Stayed 6 nights in Nov 2018
Response from VrboOwner on 13 January 2025
Thank you for taking the time to review your experience with us for future guests! We appreciate your thoughtful feedback and are so ecstatic to hear you enjoyed your stay with us. If you ever find yourself back in Key West, we would love the chance to host you again. Best, VHKW
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