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
Walk to Duval Street
5 bedrooms3+ bathroomsSleeps 10
Popular amenities
Private pool
Hot tub on site
Kitchen
Washing machine
Air-conditioning
Fenced yard
Explore the area
Key West, FL
Duval Street
Place, Duval Street
3 min walk
Mallory Square
Place, Mallory Square
7 min walk
Harry S. Truman Little White House
Place, Harry S. Truman Little White House
8 min walk
Key West, FL (EYW-Key West Intl.)
Airport, Key West, FL (EYW-Key West Intl.)
12 min drive
Rooms & beds
5 bedrooms (sleeps 10)
Bedroom 1
1 Queen Bed
Bedroom 2
2 Single Beds
Bedroom 3
2 Single Beds
Bedroom 4
1 King Bed
Bedroom 5
1 King Bed
3 bathrooms, 1 half bathroom
Bathroom 1
Bathroom 2
Bathroom 3
Bathroom 4
Spaces
Porch or lanai
Kitchen
Office
Separate dining area
Garden
Dining area
About this property
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbean with stunning island-modern that we have seen. An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West Victorian house plus Caribbean bungalow cottage.
Located in Key West’s famous Old Town Historic Seaport neighborhood on two full lots, The Caroline House Estate vacation rental is comprised of two dwellings – a classic 2-story Key West Victorian house, and a hidden 1 ½ story Caribbean bungalow.
THE CAROLINE HOUSE (Main Victorian House)
INTERIOR LAY OUT: (Downstairs)
Entrance: The arts-and-crafts staircase defines the luxurious entrance to the house and leads to the 2nd floor straight ahead, where the three bedrooms in the main house are found. The expansive runs of original heart pine wood that make the interior walls of the house have been painted with absolutely brilliant tropical colors you find on the feathers of a scarlet macaw parrot. Downstairs - left side (as you face the house): Immediately to your left of the staircase is a spacious entrance hall, fit to receive the most discerning guest. Take an immediate left again to find the fabulous Victorian sitting room with yellow-gold painted walls and styled in eclectic tropical modern fashion. Cushy floral barrel chairs surround a round bamboo and glass coffee table and prints of colorful parrots the sitting room walls.
A square arch leads directly to the next room, a bright red dining room furnished with an oversized round mahogany dining table and chairs. The interior decorator has perfectly placed a long mahogany side board that runs the entire length of the dining room under the sash windows. A striking bouquet of red coral is placed in the middle, and then framed with a pair of clear designer lamps topped with coral red shades to match.
Another square arch flows directly from the dining room to the spacious living room where a designer sofa and chairs have been chosen for comfort and style. The large wicker sofa with nautical striped upholstery is flanked by an oversized ottoman that doubles as a lounge table. A pair of khaki print occasional chairs and an antique side table is set to the side. A large flat-screen TV is prominently placed in the living room for group enjoyment, and mounted above the TV is an impressive taxidermy of a sword fish.
Straight ahead is yet a third square arch that melds into the left side of the spacious kitchen, where a double set of French doors lead to the spacious deck and swimming pool. But before we consider details of the kitchen and the pool grounds let’s look at the right side of the downstairs starting from the front.
Downstairs – right side (as you face the house): The classic hard wood front entrance hall points all the way to the back of the house where your senses are ultimately treated to a remarkable blend of a Key West historical kitchen with contemporary culinary luxury. But first, on the way to the kitchen, you pass through a beautiful office kiosk that is set with a wooden desk large enough for two. Folk-art prints from Mario Sanchez and a rustic shutter create a charming Key West office décor. Continue through to the other end of the office to the right side of the living room, and then a final interior passage joins the living room with the kitchen.
The spacious sunlit kitchen is spectacular. It encompasses most of the back of the house and feels even grander with the 12 foot high ceilings, and pendulum designer lighting that show it all off. One entire wall, from floor to ceiling, is tiled with a period correct blue and white Spanish design pattern. Against the traditional tiled wall is the contrasting modern bright white cabinets and glistening stainless steel chef’s kitchen. A large dark wooden table creates an elegant dining area for in-kitchen meals, and is joined via French doors with the back sun deck and swimming pool. Finally, at the very back of the house, off the kitchen, is a walk-in laundry room and a half-bath. There is an outdoor shower just outside the door near the laundry room and downstairs bathroom.
Upstairs - Back to the front door entrance of the main house, the staircase leads to the 2nd floor where you find three beautifully appointed bedrooms off the hallway. The first bedroom is the master suite. Luxuriously styled in tropical gold walls and bedding of soft shades of tropical pink and green, it’s set toward the back of the house and furnished with a traditional king size four-poster mahogany bed, upscale matching Caribbean style furnishings, original art, and a 42” flat screen TV. The completely modernized en-suite bathroom for this bedroom is done vintage style with mahogany vanity and double size walk in shower with dual shower heads.
Next in line down the hallway is the 2nd bedroom. Situated in the middle of the hall, it is very comfortable and offers a 27” flat screen TV. Providing two twin beds and sweetly decorated in pretty shades of coral pink and white with sea-grass headboards, it is possible to push the beds together to make a king size bed.
The 3rd bedroom is at the end of the hall at the front of the main house. Shown in our slide show with a blue and white comforter, walls painted sun yellow create a striking contrast for the queen size mahogany pencil poster bed and matching wood and wicker furnishings. This bedroom also provides a 27” flat screen TV.
Both the 2nd and 3rd bedrooms share a large luxury bathroom with soak tub and in-tub shower that is located at the end of the hall near the top of the stairs.
THE CAROLINE COTTAGE (Caribbean Bungalow Cottage) INTERIOR LAYOUT:
Set on the lot next door to the main house on the other side of the pool garden, is the 1930’s free-standing Caribbean bungalow cottage. A brass plaque on the outside announces you have arrived at ‘The Caroline Cottage.’ From the outside, it maintains it’s traditional historic cottage charm, but inside is a completely different story.
As with the main house, the staircase in the cottage defines the entrance and is also the center piece for the entire interior. The architect made a dramatic statement by taking the ceiling line clear up to the roof timbers. Then the builder hand-crafted an outrageous wooden winding staircase to reach the 2nd floor sleeping loft that was made possible with the extreme vaulted ceiling. The sleeping loft is cozy and feels a bit like a secret hiding place when you’re up there.
The compact yet well designed and fully equipped kitchen lines one corner of the cottage and is ideally set to serve as a preparation kitchen for entertaining guests. Beautiful tropical furnishings and soft goods fill every room. A 52” TV is placed for easy viewing throughout the main room.
The master bedroom, located directly off the living room space, provides a chocolate color wicker king size bed that makes a stunning contrast against the flamingo pink walls. On the wall directly opposite the bed is a flat screen TV. The entire cottage is finished with beautiful hard wood floors that compliment the staircase. The cottage provides one full beautiful bathroom on the main floor with a bath tub and in-tub shower.
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. PARKING: There is off-street parking for a maximum of 2 vehicles at The Caroline House Estate. Park in the driveway is to the left of the main house on Caroline Street, one vehicle in front of the other.
Parking is challenging in Old Town Key West and parking meters and parking lots are relatively expensive. Since this part of the island was developed before there were cars, this should be expected. It is best to park your car, remove your valuables, lock it, and forget about it when you are here. Enjoy your location and walk or bike everywhere if possible.
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PARKING: There is off-street parking for a maximum of 2 vehicles at The Caroline House Estate.
Important information
You need to know
Property # 1431341vb
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
About the area
Key West
Located by the sea, this holiday home 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. Sails To Rails Museum at Flagler Station and Mel Fisher Maritime Museum 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.
Oldest House Museum and Garden - 5 min walk - 0.4 km
Florida Keys Beaches - 6 min walk - 0.5 km
Mallory Square - 7 min walk - 0.7 km
Harry S. Truman Little White House - 8 min walk - 0.7 km
Getting around
Key West, FL (EYW-Key West Intl.) - 10 min drive
Restaurants
Sloppy Joe's Bar - 5 min walk
Conch Republic Seafood Company - 6 min walk
Kermit's Key West Key Lime Shoppe - 2 min walk
Schooner Wharf Bar - 3 min walk
Irish Kevin's - 4 min walk
Frequently asked questions
Does The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport?
As of 29 Aug, 2026, prices found for a 1-night stay for 2 adults at The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport on 20 Sept, 2026 start from S$5,744, 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 The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport pet-friendly?
No, pets are not allowed at this property.
What time is check-in at The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport?
Check-in begins at 4:00 PM.
What time is check-out at The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport?
Checkout is at 10:00 AM.
Where is The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport located?
Located in Key West Historic District, this holiday home is within a 5-minute walk of Key West Bight Marina and Duval Street. Florida Keys Beaches and Mallory Square are also within 10 minutes.
About the host
Hosted by VHKW - Vacation Homes of Key West
Languages:
English
Premier Host
They consistently provide great experiences for their guests