Entire home

Classic Key West Estate

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Reviews
9.4 out of 10 Exceptional
7 bedrooms5+ bathroomsSleeps 16421 sq m

Popular amenities

  • PoolPoolPool
  • Free WiFiFree WiFiFree WiFi
  • WasherWasherWasher
  • DryerDryerDryer
  • Air conditioningAir conditioningAir conditioning
  • KitchenKitchenKitchen

Enjoy the area

Map
Key West, FL
  • Popular LocationDuval Street7 min walk
  • Popular LocationErnest Hemingway Home and Museum15 min walk
  • Popular LocationMallory Square16 min walk
  • AirportKey West, FL (EYW-Key West Intl.)12 min drive

Most relevant reviews

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
Balcony
Separate dining area
Garden
Dining Area

About this property

Classic Key West Estate

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.

DOWNSTAIRS:

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.

Left side (facing the front of the house):

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.

Backyard of the house:

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.

UPSTAIRS

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.

Upstairs Right side (facing the front of the house):

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.

Upstairs Left side (facing the front of the house):

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 to unite, is not suitable for staging loud parties. Smoking permitted outside only. No pets please. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.

Property manager

Vacation Homes of Key West (VHKW)
Premier Host
Premier Host

Languages

Czech, English

Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

House Rules

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

Children

Adults only

Events

No events allowed

Pets

No pets allowed

Smoking

Smoking is not permitted

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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
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 not indicated whether 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 villa is in Key West Historic District, 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. Discover the area's water adventures with nearby power boating, or enjoy the great outdoors with hiking/biking trails.
Map
Key West, FL

What's nearby

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

Getting around

  • Key West, FL (EYW-Key West Intl.) - 13 min drive

Restaurants

  • The Waterfront Brewery - 7 min walk
  • Cuban Coffee Queen - 5 min walk
  • Willie T's - 8 min walk
  • Kermit's Key West Key Lime Shoppe - 8 min walk
  • Harpoon Harry's - 4 min walk

Frequently asked questions

Does Classic Key West Estate have a pool?

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

Is Classic Key West Estate pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Classic Key West Estate?

Check-in begins at 4:00 PM.

What time is check-out at Classic Key West Estate?

Checkout is at 10:00 AM.

Where is Classic Key West Estate located?

Located in Key West Historic District, this villa 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

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 22 out of 30 reviews" "
Rating 8 - Good. 7 out of 30 reviews" "
Rating 6 - Okay. 0 out of 30 reviews" "
Rating 4 - Poor. 0 out of 30 reviews" "
Rating 2 - Terrible. 1 out of 30 reviews" "

9.8/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

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

Todd 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

About the host

Hosted by Vacation Homes of Key West (VHKW)

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Why they chose this property

What makes this property unique

Languages:

English, Czech

Premier Host

Premier Host
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