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  • (305) 294-7358
Key West Time
September 22nd
5:46am · 79°F

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.

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special rates available

Sept 18- Sept 28
Weekly $4950

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Dates Weekly Nightly Terms
Aug 9, 2019 - Oct 19, 2019 $5550$11504 night min. or 3 night min. 60 days prior to arrival.
Oct 20, 2019 - Oct 26, 2019 $9200$18007 night minimum
Oct 27, 2019 - Nov 3, 2019 $5550$11504 night min. or 3 night min. 60 days prior to arrival.
Nov 4, 2019 - Nov 10, 2019 $6350$13507 night minimum
Nov 11, 2019 - Nov 22, 2019 $5550$11504 night min. or 3 night min. 60 days prior to arrival.
Nov 23, 2019 - Nov 29, 2019 $6350$13507 night minimum
Nov 30, 2019 - Dec 20, 2019 $4750$11504 night min. or 3 night min. 60 days prior to arrival.
Dec 21, 2019 - Dec 27, 2019 $7875$15007 night minimum
Dec 28, 2019 - Jan 3, 2020 $9375$18007 night minimum
Jan 4, 2020 - Jan 10, 2020 $6700$14004 night min. or 3 night min. 60 days prior to arrival.
Jan 11, 2020 - Jan 17, 2020 $6700$14004 night min. or 3 night min. 60 days prior to arrival.
Jan 18, 2020 - Jan 24, 2020 $6700$14004 night min. or 3 night min. 60 days prior to arrival.
Jan 25, 2020 - Jan 31, 2020 $7200$14005 night min, but 3-4 nights within 60 days
Feb 1, 2020 - Feb 14, 2020 $8000$14007 night minimum - Sat/Sat Only
Feb 15, 2020 - Feb 21, 2020 $8400$14007 night minimum - Sat/Sat Only
Feb 22, 2020 - Apr 17, 2020 $8000$14007 night minimum - Sat/Sat Only
Apr 18, 2020 - May 24, 2020 $6350$13504 night min. or 3 night min. 60 days prior to arrival.
May 25, 2020 - Jun 12, 2020 $5650$11504 night min. or 3 night min. 60 days prior to arrival.
Jun 13, 2020 - Aug 7, 2020 $6350$13505 night min, but 3-4 nights within 60 days
Aug 8, 2020 - Oct 15, 2020 $5650$11504 night min. or 3 night min. 60 days prior to arrival.
Oct 16, 2020 - Oct 24, 2020 $9325$15007 night minimum
Oct 25, 2020 - Nov 7, 2020 $5650$11504 night min. or 3 night min. 60 days prior to arrival.
Nov 8, 2020 - Nov 15, 2020 $6350$13507 night minimum
Nov 16, 2020 - Nov 19, 2020 $5650$11504 night min. or 3 night min. 60 days prior to arrival.
Nov 20, 2020 - Nov 28, 2020 $6350$13507 night minimum
Nov 29, 2020 - Dec 18, 2020 $4850$11504 night min. or 3 night min. 60 days prior to arrival.
Dec 19, 2020 - Dec 25, 2020 $8000$15007 night minimum
Dec 26, 2020 - Jan 1, 2021 $9500$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 -

Apply here for Travel Guard Trip Cancellation and Interruption Insurance.

VHKW offers promotional specials for purchasing trip insurance for stays between Aug 10 and Oct 20. Please call for more details.

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)
Aug 26, 2019,
Tremendously enjoyable time staying at The Caroline House. The home provided our extended family the opportunity to spend quality time with each other every day during our stay. There was also enough space for everyone to have privacy, yet feel comfortable and relaxed. The pool shrouded in native vegetation made us forget we were staying in the city. The convenience to all of the amenities - both the marinas and the Duval St. atmosphere was a privilege. VHKW did a great job for us before, during and after our stay - Thank you !

Jul 14, 2019,
We had an excellent stay! The house is well appointed and very pretty. Despite some issues with the blow up beds, the maintenance people addressed it satisfactorially. Thank you.

Jun 05, 2019,
Great home for a group to enjoy. All the little details and needs are considered and the house is stocked ! Great location with access to Duval .

Apr 03, 2019,
We had a wonderful vacation in Florida, and thoroughly enjoyed our stay at vacation homes of key west. Our accommodations were 5 star quality, and all of our questions were answered immediately. The beautiful home, and pool area were very comfortable, and very organized. Our reservations, and stay were very professionally managed. We loved each room, and everyone had a favorite spot to relax. The pool and hot tub were very comfortable, and we enjoyed our time on the patio. Thank you for making our vacation a trip we will always remember.

Jan 31, 2019,
The Caroline Estate was perfect for our extended stay in January. Great location, great pool and hot tub, and plenty of room. All our guests said great things about the main house and cottage accommodations. Best of all the weather cooperated! We plan to return to this property.

Jan 20, 2019,
Awesome house and location. Some dated pool and television equipment caused us to call for assistance several times, but they came within a reasonable time. Parking is tight for 2 large cars. Otherwise, it was incredible (CAROLINE HOUSE) and we WILL be back!

Oct 25, 2018,
House was great. People responded pretty quickly to a leak in the attic. Other than one afternoon / evening of leak and repair there were no interruptions. Pool and courtyard were great as was location.

Oct 13, 2018,
A pleasure to work with. House was fantastic!

Aug 27, 2018,
Always helpful and professional.

Jul 01, 2018,
Awesome property, lovely amenities and great location! Paige was awesome through the rental processes.

May 31, 2018,
Caroline House was absolutely amazing. We loved the cottage adjacent to the main house. Had a wedding rehearsal dinner with 15+ adults. There was plenty of space in kitchen to accommodate all the cooking requirements. Pool and spa combo was great for the kids. Location was perfect for all your needs. Would definitely stay again.

May 17, 2018,
Once again, a great experience, both with the Caroline House and the staff at VHKW. We'll be back next year. Thank you.

Jan 08, 2018,
Loved the house. It was so great having my family together for the holiday we had plenty of room. My young adult grandchildren enjoyed having the cottage to themselves and being so close to the night life of Duval st. Weather was beautiful.

Oct 09, 2017,
I've spoken with Paige at VHKW who has been extremely courteous and professional even with the situation Hurricane Irma created. She found a solution for our groups problems. I would recommend this agency to anyone and will not hesitate to use in the future.

Sep 14, 2017,
We had an awesome time at The Caroline House during our stay. The house was perfect, and the location to Duval St. and other attractions was great. We hope Hurricane Irma didn't do too much damage to this beautiful house.

Aug 21, 2017,
The Caroline House is our favorite home to rent in Key West. After 35 years of traveling for lobster season, we are always thrilled to get it if it is available. While we had a couple of issues like the air in the guest house not working when we arrived, VHKW had someone out on a Sunday within 35 minutes. Serious Service! Will rent again!

Aug 07, 2017,
Great house, very well equipped kitchen which you never see with rentals. Really think a midweek trash pickup should be arranged when there is a large party. Thanks

May 09, 2017,
Exceptional! We look forward to staying at the Caroline House again next year.

Dec 20, 2016,
Excellent service and house. Will return 2 times a year!!

Dec 08, 2016,
Well appointed, convenient, comfortable set up and supplies. Everything is well taken care of and clean. Beds incredibly comfortable. Everything you'd need for a family and elegant enough for a luxury getaway.

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