The Caroline House Estate ~ Weekly Rental

5BR 3.5BA ~ Weekly Rental
Sleeps 10

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. Displaying a perfected tropical style the architect and designer artfully intertwined a romantic look-back into architectural history with a superior eclectic cosmopolitan island charm.

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 curb-side view is of the nouvelle-Victorian house that displays all the Key West style of it’s gracious historic neighbors while offering all the modern amenities. Classic front porches outline the entire width of the 1st and 2nd floors and an abundance of sash windows outlined in traditional wooden shutters and French doors invite in the sunlight. Pale blue porch ceilings reflect the historic island authenticity of the house along with the essential white picket fence made complete with capital posts and a lantern lamp with lights that appear to flicker like candles.    

THE CAROLINE HOUSE  (Main Victorian House)


A brass plaque on the outside wall near the door announces you have arrived at ‘The Caroline House.’ Once inside the house, the stunning blend of the-old-with-the-new begins right away. You are first met with the welcoming charm of the Key West Victorian wooden banister staircase that is situated to the front-right side of the house. 

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. A bold move in such a classic historic home, the colors are balanced at the impressive 12 foot tall ceilings with traditional wide white crown molding, and then perfectly paired below with original restored varnished wooden floors.

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. Carefully chosen art pieces, real sea shells and decorative lamps are masterfully placed and grass mat rugs complete the up-scale tropical look of the room.

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. A free-standing sink set against the original heart pine walls captures the romantic era of this remarkable home.

At the opposite end of the bedroom hallway, at the front of the house, is a single pane French door that leads to the 2nd floor porch that runs the entire width of the house and offers a beautiful down-look view of Caroline Street below.

THE CAROLINE COTTAGE  (Caribbean Bungalow Cottage)


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. Completely modernized to luxurious standard, like the main house in the estate, no detail has been overlooked.

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.  Two twin beds make an inviting sleeping nook with a view to main room below. 

The interior designer makes the same bold move in the cottage as the main house by choosing bright gradient shades of pink and white. The main room in the cottage includes a living / dining / kitchen area. Elegant white woven furnishings have been kept simple and sleek. As with ‘The Caroline House,’ the interior designer selected furnishings for ‘The Caroline Cottage’ that are sophisticated yet casual and elegant.

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 32” 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.

An incredible feeling of exclusive intimacy has been masterfully created in the pool garden for The Caroline House Estate vacation rental.  Located between the main Victorian house, ‘The Caroline House,’ and the Caribbean bungalow, ‘The Caroline Cottage,’ is a large (by Key West standards) free-form swimming pool, spacious pool deck, and lush tropical landscaping. Set as an outdoor living space right off the kitchen and living room of the main house, the pool garden and sun deck will invite you to spend many hours right here. Lounge and patio furniture has been placed for relaxing and sunning. All you need is a cool drink and a good book.


Bedding Summary:

Main Victorian House

All bedrooms are on the 2nd floor.

  • Master Bedroom – King Sized bed
  • Middle Bedroom – 2 Twin beds (can be made as a King)
  • Front Bedroom – Queen Size bed

The Caroline Cottage 

  • Downstairs – Master Bedroom – King Sized bed
  • Loft – 2 Twin beds (cannot be made into a King)

Parking: Off-Street parking for 1-2 cars maximum in the driveway – one in front of the other. It is recommended that you leave your car behind and plan on walking and biking if you are able. From this location you do not need a car. Enjoy walking or biking everywhere—you'll see more that way.

Amenities: Upscale Amenities generally reserved for an exclusive Resort. Heated free-form swimming pool, tropical landscaping, and outdoor deck. Main house has gourmet kitchen with top-of-the-line appliances; cottage has 2nd full kitchen. BBQ grill, Central air conditioning, full laundry room, Audio Visual Systems, DSL Internet, HD TV. TV’s in all rooms except the loft in the cottage

Activities: Close to adventures and activities including sailing, boating, diving, museums, nightlife. Conveniently located near Fausto's Fine Food Palace gourmet grocery store offering excellent wine selection, sushi deli, and butcher; Close to boutique shopping, art galleries, and a variety of national and international restaurants, coffee shops. Close to the beach.

Area: The famous historic Old Town Key West waterfront on the gulf side of the island and the original lower Duval Street area, encompasses this district. Here the founding fathers and mothers of the late 1800's built the first shipping docks and warehouses, restaurants and grand homes, that stand today as one of the largest and most impressive collection of turn-of-the-century architecture. From larger Greek Revival Victorians to charming shot gun cottages, many of these alluring structures have been restored and renovated to stand in their gleaming glory.

Restrictions: This is a SMOKE FREE house. Absolutely no pets please! We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.

Notes: It is very rare to find a private home estate with amenities generally reserved for an exclusive resort offered as a licensed weekly vacation rental. The design of this estate property makes it ideal for sophisticated individuals with discerning tastes and is suited for a family or executive group looking for the very finest Key West has to offer. This home should never be considered as an option for travelers looking to stage a party or any kind of event.

This property is intended for a family, professionals and executives who are looking for a private estate home with upscale Quality Amenities.

Main Victorian House - All bedrooms are on the 2nd floor

  • Master Bedroom – King Sized bed
  • Middle Bedroom – 2 Twin beds (can be made as a King)
  • Front Bedroom – Queen Size bed

The Caroline Cottage 

  • Downstairs – Master Bedroom – King Sized bed
  • Loft – 2 Twin beds (cannot be made into a King)
Dates Weekly Nightly Terms
Oct 23, 2016 - Oct 29, 2016 $9100$18007 night minimum
Oct 30, 2016 - Nov 6, 2016 $5300$11505 night minimum
Nov 7, 2016 - Nov 13, 2016 $6200$13507 night minimum
Nov 14, 2016 - Nov 18, 2016 $5300$11505 night minimum
Nov 19, 2016 - Nov 25, 2016 $6200$13507 night minimum
Nov 26, 2016 - Dec 17, 2016 $4500$11503 night minimum
Dec 18, 2016 - Dec 25, 2016 $7600$14007 night minimum
Dec 26, 2016 - Jan 1, 2017 $9100$18007 night minimum
Jan 2, 2017 - Jan 13, 2017 $6300$14007 night minimum
Jan 14, 2017 - Jan 20, 2017 $8800$14007 night minimum
Jan 21, 2017 - Jan 27, 2017 $6300$14007 night minimum - Sat/Sat Only
Jan 28, 2017 - Feb 3, 2017 $6800$14007 night minimum - Sat/Sat Only
Feb 4, 2017 - Feb 17, 2017 $7600$14007 night minimum - Sat/Sat Only
Feb 18, 2017 - Feb 24, 2017 $8000$14007 night minimum - Sat/Sat Only
Feb 25, 2017 - Apr 21, 2017 $7600$14007 night minimum - Sat/Sat Only
Apr 22, 2017 - May 29, 2017 $6200$13504 night min. or 3 night min. 60 days prior to arrival.
May 30, 2017 - Jun 16, 2017 $5300$11504 night min. or 3 night min. 60 days prior to arrival.
Jun 17, 2017 - Aug 11, 2017 $6200$13507 night min. or 3 night min. 60 days prior to arrival.
Aug 12, 2017 - Oct 21, 2017 $5300$11507 night min. or 3 night min. 60 days prior to arrival.
Oct 22, 2017 - Oct 28, 2017 $9100$18007 night minimum
Oct 29, 2017 - Nov 5, 2017 $5300$11505 night minimum
Nov 6, 2017 - Nov 12, 2017 $6200$13507 night minimum
Nov 13, 2017 - Nov 17, 2017 $5300$11505 night minimum
Nov 18, 2017 - Nov 24, 2017 $6200$13507 night minimum
Nov 25, 2017 - Dec 16, 2017 $4500$11503 night minimum
Dec 17, 2017 - Dec 25, 2017 $7600$14007 night minimum
Dec 26, 2017 - Jan 1, 2018 $9100$18007 night minimum
Jan 2, 2018 - Jan 12, 2018 $6450$14007 night minimum
Jan 13, 2018 - Jan 19, 2018 $8900$14007 night minimum
Jan 20, 2018 - Jan 26, 2018 $6450$14007 night minimum - Sat/Sat Only
Jan 27, 2018 - Feb 2, 2018 $6950$14007 night minimum - Sat/Sat Only
Feb 3, 2018 - Feb 16, 2018 $7750$14007 night minimum - Sat/Sat Only
Feb 17, 2018 - Feb 23, 2018 $8150$14007 night minimum - Sat/Sat Only
Feb 24, 2018 - Apr 20, 2018 $7750$14007 night minimum - Sat/Sat Only
Apr 21, 2018 - May 27, 2018 $6350$13504 night min. or 3 night min. 60 days prior to arrival.
May 28, 2018 - Jun 15, 2018 $5450$11504 night min. or 3 night min. 60 days prior to arrival.
Jun 16, 2018 - Aug 9, 2018 $6350$13507 night min. or 3 night min. 60 days prior to arrival.
Aug 10, 2018 - Oct 20, 2018 $5450$11507 night min. or 3 night min. 60 days prior to arrival.
Oct 21, 2018 - Oct 27, 2018 $9100$18007 night minimum
Oct 28, 2018 - Nov 4, 2018 $5450$11505 night minimum
Nov 5, 2018 - Nov 11, 2018 $6350$13507 night minimum
Nov 12, 2018 - Nov 16, 2018 $5450$11505 night minimum
Nov 17, 2018 - Nov 23, 2018 $6350$13507 night minimum
Nov 24, 2018 - Dec 16, 2018 $4650$11504 night min. or 3 night min. 60 days prior to arrival.
Dec 17, 2018 - Dec 25, 2018 $7750$15007 night minimum
Dec 26, 2018 - Jan 1, 2019 $9250$18007 night minimum

Additional Notes:

  • High Season generally requires a 7 night minimum stay. Shorter stays of 3 - 5 nights may be available within 60 days of your arrival date or in special situations. Certain dates may not be available if they minimize optimal booking for the property's reservation calendar. Please contact us to inquire about stays less than 7 nights.
  • Shoulder and Low Season is a 3 - 5 night minimum available on reservations made within 60 days of arrival May through mid-August. From mid-August through mid-December, 3 - 5 night minimum stays are available any time.
  • Short Stays are available if there are open nights that are less than the minimum stay, shorter stays may be possible depending on the property. Please contact us to inquire.
  • Holiday, Festival, and Event Rates are 20% to 25% higher. These include, but are not limited to: Fantasy Fest, New Years, Key West Yacht Race Week, Thanksgiving, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, Biker's Poker Run, 4th of July, Easter. A 7 night minimum stay is required for most major holidays, festivals, and events.

Rates and Terms are subject to change without notice. Above rates do not include taxes and fees. Click here for more details on additional fees. Please contact us for specific pricing and to confirm rates. Rates in US Funds. (305) 294-7358 Ext 1 -

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