Entire home

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

street view
pool
street view
street view
pool

Reviews

9.2 out of 10
Wonderful
7 bedrooms5+ bathroomsSleeps 16421 sq m

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Kitchen
  • Pool
  • Barbecue grill

Explore the area

Map
Key West, FL
  • Duval Street
    ‪7 min walk‬
  • Ernest Hemingway Home and Museum
    ‪15 min walk‬
  • Mallory Square
    ‪16 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪12 min drive‬

Rooms & beds

7 bedrooms (sleeps 16)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Double Beds

Bedroom 4

1 Double Murphy Bed

Bedroom 5

1 King Bed

Bedroom 6

1 King Bed

Bedroom 7

1 King Bed

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
Kitchenette
Balcony
Separate dining area
Garden
Dining area

About this property

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

Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation rental is at once historic and exotic. If you've ever had the opportunity to stroll the residential streets of the famous Key West Historic Seaport neighborhood, you have experienced first-hand the type of incredible architectural history embodied in this authentic turn of the 19th Century property. The location of this estate property is where you'll find some of the most iconic destinations on the island.

Displaying an abundance of elegant Victorian design, artisan ship carpenters milled elaborate gingerbread trim that the front of the 7 BR 5.5 BA Classic Key West Estate home. Deep porches with turned columns grace the entire width of the first and second floor porches. Beautiful stained glass transom windows top symmetrically set French doors. Oversized windows surround the home to invite in the light and tropical breezes. A beautiful pool-side pied-a-terre, in the private back yard, provides the perfect touch of fantasy. The quintessential white picket fence with capital topped posts gracefully surrounds the front yard to complete the perfect picture of opulence.

Interior Layout: Throughout the years, the interior of this home has mostly, retained its original layout. Many of the walls in the house feature the revered heart pinewood planks used to build this home in the late 1800’s. During renovations in the 1970’s, much of this long extinct pinewood, was meticulously hand-sanded by craftsman to reveal its natural warm glow.

Throughout the Classic Key West Estate, the historic rooms are furnished and decorated with up-scale tropical furniture and pleasing artwork. Featured on one living room wall, is a commissioned historiography art piece that depicts the timeline of this estate. It was researched and created by local professional historian Sharon Wells.

A classic 1800’s Federal style center-hall makes an impressive entrance statement. Step inside and the wide 1st floor hallway leads to the back of the house. Stately rooms with 12- foot ceilings line both sides of the house. The wooden banister staircase was intricately carved by early artisans. It provides the visual center point of the first floor.

Right side (facing the front of the house): On the front right side of the staircase is the spacious living / media room. It is nicely furnished in light tropical colors with traditional wood and wicker furnishings. A 50-inch TV provides the focal point for shared media entertainment.

The living / media room is open to the dining room via an expansive wooden archway. The dining room is nicely staged for group dining. A single door at the back wall of the dining room leads to the upscale kitchen.

The kitchen was stylishly renovated with luxury upgrades. Walls are painted a dramatic blue, in striking contrast with the bright white cabinets, stainless steel appliances, and earth tone granite counter tops.

The kitchen is located at the back of the house. This is ideal for enjoying the indoor / outdoor Key West lifestyle. Two sets of French doors, at the back corner of the kitchen, lead to the pool and deck area.

Bedroom One: Returning to the front of the house, the first room on the left is bedroom one. Nicely decorated to double as an office / den, it has a Murphy bed on one wall. The bed makes up as a comfortable queen size bed.

Bedroom Two: Walking toward the back of the house, the next door on the left is bedroom two. This bedroom is authentically furnished and includes a metal king-size bed, and an antique wooden dresser and armoire. This bedroom also provides an en-suite bathroom.

In contrast with the bedroom, the en-suite bathroom is a modernistic design. It is decorated in white and fitted with a double wooden vanity topped with chic composite countertops. The shower is oversized with frameless glass doors. Contrasting black bathroom fixtures add elegance to the room.

Back out to the hallway, the last room on the downstairs left is a half-bath with a sink, commode, and mirror. Conveniently located near the back yard pool it serves as the pool bath.

Pool and Deck: The most direct path to reach the back yard and swimming pool, is through the kitchen. At the back corn wall of the kitchen double sets of French doors open to the deck.

The backyard deck is set up as an outdoor lounging and dining area. A dining table with chairs are placed under a covered porch. An awning extension adds protection from the rain. The outdoor dining table is positioned near the kitchen making it easy to serve and entertain outside. For poolside media enjoyment, a flat screen TV is placed on the exterior wall above the table.

Studio Cottage – Bedroom Three: A bonus feature of this estate property is the upscale free-standing studio cottage, with a full bathroom and kitchenette. It provides two full-size (double) beds that are positioned to catch a view of the pool.

Situated across the back deck from the main house, it offers privacy from the main house. Décor is elegant with pinewood walls and open-beamed ceilings.

Returning to the front of the house, we ascend the banister staircase to the 2nd floor. The landing leads to an impressive and dramatic hallway.

At the front and back of the 2nd floor, exterior doors lead to covered porches. The front door connects with the 2nd floor covered front porch, that spans the width of the house. From up here enjoy a view of beautiful Fleming Street below.

At the back of the house, a door leads to the upstairs covered back porch. From here enjoy a view of the neighborhood rooftops and the pool-garden below.

There four bedrooms and two bathrooms upstairs. All four bedrooms are spacious and feature 10+ foot ceilings. Each upstairs bedroom is uniquely decorated yet integrated in design with the other bedrooms. All four bedrooms provide a king size bed, dresser, bedside tables, and reading lamps.

The right side of the upstairs has two spacious bedrooms and one bathroom. During an early renovation, Key West craftsmen meticulously restored the original pinewood walls on the upstairs right side of the house. The warm hand-rubbed wood honors the historic authenticity of the house.

Bedroom Four: Apart from the beauty of the wood walls and high ceilings, bedroom four has windows on two walls that invite in the natural light. The fourth bedroom offers a king-size. It also has a nice view of the covered front porch.

Bedroom Five (with en-suite bathroom): The fifth bedroom five is the next room down. It can be accessed from the hallway, or through double French doors which connect to bedroom four. You may have to flip a coin to see who gets bedroom five. Bedroom five is prominently furnished with a dark-wood canopy king-size bed and features a beautiful historic en-suite spa-bathroom.

En-suite Spa Bathroom: The Colonial-Caribbean design of this special spa bathroom creates an aire of island romance. A soaring ceiling adds to the spacious feeling and adds a dramatic flair. There is an oversize shower in one corner. A double white wood vanity sink is topped with a large antique mirror that bounces around the light. An upholstered chaise, set against the bare wood walls, give this special bathroom an exotic feel.

In elegant contrast to the bare wood walls on the right side of the upstairs, all bedroom walls on the left side are painted a soft yellow. Painted antique planks create a light backdrop to show off dark wood and wicker beds and pleasing artwork.

Bedroom Six: Returning to the front of the house, bedroom six is in the upstairs left corner. As a corner bedroom, there are two exterior walls with four large sash windows that invite in the sunlight. Bedroom six provides a king-size bed.

Bedroom Seven (with en-suite bathroom): Back to the hall and past the stairs, bedroom seven is the next in line. also provides a king-size bed. While there is only one exterior wall in bedroom seven, oversized windows assure plenty of natural light. Bedroom seven connects with a full en-suite bathroom, with a second door that leads to the hallway.

Second Upstairs Bathroom: The last room at the end hallway, on the left, is a full bathroom with shower. Bedroom four and six, at the front of the house, share this bathroom.

Grounds: The property grounds are fenced in the front and back for privacy. The back yard is decked creating a wonderful place for private entertaining complete with swimming pool, and an upstairs verandah creates a covered loggia. Beautiful palm trees and foliage create a romantic tropical setting. The front of the home has beautiful curb appeal with large front porches on the first and second floor that overlook the estate neighborhood.

Note: If your group grows, or if you just want more room to spread out, rent this home with a private Caribbean Guest House. The combination of the two houses is available to rent as the 10 BR 7.5 BA Old Town Caribbean Estate.

Activities: Walk to all old town features, no need for a car. Just 3 1/2 streets to Duval St., close to Key West Mallory Square Sunset Celebration, and a few short streets from Historic Seaport and retailers (remember it takes 3 to 4 Key West streets to equal the distance of a typical city block). Sailing, boating, diving, museums, nightlife. Conveniently located to gourmet grocery shopping with excellent wine selection. Close to shopping, art galleries, and a variety of restaurants, coffee shops. Close to the beach.

Restrictions: While this property is ideal for families and groups, it is not suitable for staging loud parties. Smoking permitted outside only. No pets please. Guests under 25 years of age must be accompanied by a family group or guardian.

PAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.

Property manager

VHKW - Vacation Homes of Key West
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted

Important information

You need to know

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
This property accepts cash
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 deadlock

We should mention

A car is not required for transport to and from this property

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 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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Key West, FL

What's nearby

  • Duval Street - 7 min walk - 0.6 km
  • Ernest Hemingway Home and Museum - 15 min walk - 1.3 km
  • Mallory Square - 16 min walk - 1.4 km
  • Southernmost Point - 4 min drive - 1.9 km
  • South Beach - 8 min drive - 1.9 km

Getting around

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

Restaurants

  • ‪The Waterfront Brewery - ‬7 min walk
  • ‪Cuban Coffee Queen - ‬5 min walk
  • ‪Kermit's Key West Key Lime Shoppe - ‬8 min walk
  • ‪Willie T's - ‬8 min walk
  • ‪Schooner Wharf 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.

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.

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 Ernest Hemingway Home and Museum are also within 1 mile (2 km).

Reviews

9.2

Wonderful

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. 25 out of 34 reviews
Rating 8 - Good. 8 out of 34 reviews
Rating 6 - Okay. 1 out of 34 reviews
Rating 4 - Poor. 0 out of 34 reviews
Rating 2 - Terrible. 1 out of 34 reviews

9.6/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.6/10

Location

9.6/10

Listing accuracy

Reviews

10/10 Excellent

Karen S.

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

10/10 Excellent

lori r.

Liked: Cleanliness, check-in, communication, listing accuracy
Disliked: Location
Stayed 7 nights in Dec 2024

6/10 Okay

Debbie R.

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

10/10 Excellent

Monica N.

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

8/10 Good

Holly S.

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

10/10 Excellent

Joanne S.

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

10/10 Excellent

Nick D.

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

10/10 Excellent

Nat D.

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

10/10 Excellent

Thomas B.

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

10/10 Excellent

Cindy W.

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

Great place for a large group

We had a group of 16 friends and family. The house is beautiful and has plenty of room. It is very clean. Lots to do nearby.
Stayed 5 nights in Jun 2022

10/10 Excellent

Stacey T.

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

Amazing

Beautiful home and location. We loved the back deck and the front porch and a bathroom for everyone
Stayed 5 nights in May 2022

10/10 Excellent

Steven P.

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

10/10 Excellent

Charles T.

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

Key West 2021

The house was very nice. Plenty of room for all 14 of us. The only thing that I was not impressed with was the cleanliness of the outside of the house. Walkways were cluttered and the plants needed to be cleaned up.
Stayed 7 nights in Nov 2021

8/10 Good

Adam M.

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

10/10 Excellent

Jim M.

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

50th Birthday Bash

Fourteen of us stayed at the property to celebrate a friend's 50th birthday. Great vacation!
Stayed 7 nights in May 2021

10/10 Excellent

Victoria K.

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

Big house with a nice little pool

We enjoyed this nicely located property with a wonderful pool out in the back. My teens loved the private house by the pool, and my in laws appreciated the master on the first floor. We walked everywhere, and there were ample restaurants close by.
Stayed 7 nights in Mar 2021

10/10 Excellent

mary a.

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

Great House in a Great Location!

Super cool house with lots of history. It had plenty of room for our family and friends. Is in walking distance to all Key West has to offer. We had a blast and would definitely stay again. Thank you!!
Stayed 7 nights in Mar 2021

10/10 Excellent

Carolyn V.

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

10/10 Excellent

Stephanie D.

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

House is wonderful

We had 12 family members staying here for a week to celebrate Thanksgiving. We had a great time. We didn’t rent a car and just walked everywhere. There is a grocery store three blocks away. Our favorite place to gather was the area around the pool. It’s so comfortable and pleasant. We would all come back here in a heart beat.

10/10 Excellent

Shantell and JR G., Rosharon, Texas

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

8/10 Good

Maura M.

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

10/10 Excellent

Shawn S.

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

Covid Key West

Much less crowds and chaos so I actually enjoyed the stay even more! Close to everything and had 5 star food experiences everyday within walking distance.

10/10 Excellent

Rick D.

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

Great week in Old Key West

Fantastic experience. Great location, enough room for our group of 14. Walking distance to almost everything.
Stayed 7 nights in Feb 2020

10/10 Excellent

p w.

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

Beautiful estate home in key west

This home was the perfect venue for our large family to stay at for our week in key west. Large bedrooms and common areas and the kitchen is stocked with everything you need to feed a large group. It’s conveniently located to everything with a grand front porch to watch the world go by.
Stayed 6 nights in Jan 2020

10/10 Excellent

Alexandria S.

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

About the host

Hosted by VHKW - Vacation Homes of Key West

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests