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  • (305) 294-7358
Key West Time
May 28th
9:06am · 86°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.

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 acclaimed restaurants, coffee shops. Close to the beach. Easy walk to the famous Mallory Square Sunset Celebration, Custom House Museum, and the Key West Aquarium. Live theatre performances and concerts nearby are offered at the Waterfront Theatre, The Red Barn Theatre, The Studios of Key West, Key West Theater and the Key West Amphitheater.

Area: The famous Key West Historic 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.

Payment by credit card will be subject to 3.85% surcharge.

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special rates available


June 8- June 13
June 27 - July 6

Nightly $1250
Weekly $6500

view all specials

Dates Weekly Nightly Terms
Apr 13, 2024 - May 29, 2024 $8445$1500.004 night min. or 3 night min. 60 days prior to arrival.
May 30, 2024 - Jun 9, 2024 $7510$1450.004 night min. or 3 night min. 60 days prior to arrival.
Jun 10, 2024 - Aug 11, 2024 $8445$1500.005 night min, but 3-4 nights within 60 days
Aug 12, 2024 - Oct 2, 2024 $6645$1250.004 night min. or 3 night min. 60 days prior to arrival.
Oct 3, 2024 - Oct 17, 2024 $7100$1350.004 night min. or 3 night min. 60 days prior to arrival.
Oct 18, 2024 - Oct 27, 2024 $12395$2125.007 night minimum
Oct 28, 2024 - Nov 3, 2024 $7510$1450.004 night min. or 3 night min. 60 days prior to arrival.
Nov 4, 2024 - Nov 11, 2024 $8445$1500.007 night minimum
Nov 12, 2024 - Nov 21, 2024 $7510$1450.004 night min. or 3 night min. 60 days prior to arrival.
Nov 22, 2024 - Nov 30, 2024 $7800$1500.007 night min. or 3 night min. 60 days prior to arrival.
Dec 1, 2024 - Dec 18, 2024 $6650$1250.004 night min. or 3 night min. 60 days prior to arrival.
Dec 19, 2024 - Dec 27, 2024 $11210$2150.007 night minimum
Dec 28, 2024 - Jan 3, 2025 $13310$2560.007 night minimum
Jan 4, 2025 - Jan 10, 2025 $9790$1870.004 night min. or 3 night min. 60 days prior to arrival.
Jan 11, 2025 - Jan 17, 2025 $9790$1870.004 night min. or 3 night min. 60 days prior to arrival.
Jan 18, 2025 - Jan 31, 2025 $10450$1970.004 night min. or 3 night min. 60 days prior to arrival.
Feb 1, 2025 - Feb 14, 2025 $11610$2070.005 night min, but 3-4 nights within 60 days
Feb 15, 2025 - Feb 21, 2025 $12100$2145.005 night min, but 3-4 nights within 60 days
Feb 22, 2025 - Apr 11, 2025 $11610$2070.005 night min, but 3-4 nights within 60 days
Apr 12, 2025 - May 28, 2025 $8445$1500.004 night min. or 3 night min. 60 days prior to arrival.
May 29, 2025 - Jun 8, 2025 $7510$1450.004 night min. or 3 night min. 60 days prior to arrival.
Jun 9, 2025 - Aug 10, 2025 $8445$1500.004 night min. or 3 night min. 60 days prior to arrival.
Aug 11, 2025 - Oct 1, 2025 $6645$1250.004 night min. or 3 night min. 60 days prior to arrival.
Oct 2, 2025 - Oct 16, 2025 $7100$1350.004 night min. or 3 night min. 60 days prior to arrival.
Oct 17, 2025 - Oct 25, 2025 $12395$2125.007 night minimum
Oct 26, 2025 - Nov 2, 2025 $7510$1450.004 night min. or 3 night min. 60 days prior to arrival.
Nov 3, 2025 - Nov 10, 2025 $8445$1500.007 night minimum
Nov 11, 2025 - Nov 20, 2025 $7510$1450.004 night min. or 3 night min. 60 days prior to arrival.
Nov 21, 2025 - Nov 29, 2025 $7800$1500.007 night min. or 3 night min. 60 days prior to arrival.
Nov 30, 2025 - Dec 19, 2025 $6650$1250.004 night min. or 3 night min. 60 days prior to arrival.
Dec 20, 2025 - Dec 27, 2025 $11210$2150.007 night minimum
Dec 28, 2025 - Jan 5, 2026 $13310$2560.007 night minimum - Sat/Sat Only

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, Thanksgiving, Christmas, New Years, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, 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)
Jan 23, 2024,
This is the second time we have used VHKW. Once again, our stay was fantastic. Our group had a wonderful time and the house was in the perfect location for us. We look forward to coming back next year, and probably many more.

Nov 28, 2023,
Year after year VHKW provides top tier service and communication. This was my 7th consecutive year renting one of their 4+ bedroom properties. The Caroline House Estate is by far my favorite property to date. There were 5 adult couples in our group. The bathroom sharing was challenging at times but certainly not a deterrent. Like all VHKW properties, this home was clean, comfortable, and had all accommodations needed for a stay in KW. The only thing better than their properties is their staff. Thank you so much for a great stay!

Aug 28, 2023,
Caroline House was very nice. Everyone thought very highly of it. Great location.

Aug 21, 2023,
Fabulous location and beautiful Key West home. Our family had a fabulous time. No major issues. Property is charming and very well kept. We were there in August and it was extremely comfortable in the main house. The guest cottage was a bit stuffy in the loft, but we made due. It’s two blocks from Duval, and is very convenient.

May 16, 2023,
Once again we had a fabulous 8 days in the Carolina House. This house provides the perfect location within walking distance to all the best bars, shopping and eateries. Look forward to staying again next year!! Perfect for our group of 10!!

Apr 17, 2023,
Great company to work with. Only rental company I use when traveling to Key West!

Jan 07, 2023,
house and location were great - only issue was washing machine

Oct 06, 2022,
Top notch company. We rent from them every trip to KW.

Jun 22, 2022,
The Caroline Estates House was absolutely Beautiful and Perfect for our Family and Friends Group of 10. The Pool Cottage was Adorable and fit in perfect for us! The pool area was very tropical and wonderful for the times we All stayed home! The location was also Perfect ? Duval Street was so close and so were all the activities we did, ie Ghost Tour, Snorkeling, Sunset Sail. Love, Love, Love this House ❤️ VHKW was also very Easy to work with so we will definitely be renting from them again!!

May 17, 2022,
Location is everything in key west and this house was perfect in every way! It easily accommodated our party of 10 and with the cottage space in the back we weren’t ever tripping over each other. The kitchen was more equipped than expected right down to the spice cabinet! The pool was a bonus after a hot day on Duval. Will definitely be reserving this for next years festival!

Mar 23, 2022,
Great service and a great house with an excellent location.

Dec 06, 2021,
You are the best team to work with thank you so very much

Nov 15, 2021,
Great experience. Top notch service and handled our few small issues with the house very quickly. We will definitely book through you again!

Jul 09, 2021,
The house was wonderful and in a great location. Everything about VHKW was great! We had excellent customer service from check in to check out. I will definitely use again when we return to Key West. It was a memorable vacation.

Jun 29, 2021,
Really beautiful house. Pool larger than photos show and room areas well planned for a larger group. Fantastic location Only improvement areas- pool might need a re-finish, and rear Cottage has a very musty smell. Interior doors (upstairs) stick a bit too. Loved the friendly iguanas!

May 25, 2021,
Great house, was clean had everything I needed to make sure my friends party was a success. Great location and all the guys loved the house. Would have paid for a late checkout if possible getting nine guys up at 10am after a weekend in the keys was like pulling teeth. Thanks again.

Mar 15, 2021,
This was a great house! Great location to everything, plenty of room, nice big kitchen, laundry, outdoor seating,... we loved it!! Thank you!!

Jan 17, 2021,
The home was amazing! Big enough to accommodate our large family and impeccably furnished. Every amenity you could possibly need was on site, which made the stay even more enjoyable. The location is close to all the action on Duval Street, without the noise and crowds. Cannot wait to return!

Nov 07, 2020,
Outstanding service and home. Perfect location.

Oct 05, 2020,
THE GOOD: Excellent location, only two blocks from Duval, harbor etc. and walk to everything! Location was the key for us and we hit it on the nail with this property, Definitely where the action is! Property is great for larger parties and well stocked with plenty of towels, pool towels and well stocked kitchen. Beds are very comfortable, no complaints here. Overall, the house was clean, inviting and comfortable. The pool is a bonus and we used it a few days it is very shady so keep this in mind when renting. Cutting off a few of the tree limbs would help a lot in allowing more sun areas. IMPROVEMENT: The pool house is great, comfortable and a great addition for large groups, but smells musty and we had to buy air fresheners. Not sure what can be done but was noticeable and hard to overlook. Also, the pool house needs a mirror in the main room as there is only one bathroom and it makes it very difficult to get ready when no mirrors anywhere else. Small items, but as they say, details matter. We had a few problems with the air conditioner which was out for four days in two of the rooms, and issues with the TV’s(just need to add a sheet of instructions). VHKW was very responsive to all our problems no complaints there as things always break, need repair etc. They did what needed to be done to help solve our problems. Overall, I recommend this house for location, cleanliness and location we were a group of 50 year old women, and while the house could use some updates, it served us perfectly for the week we stayed.

Aug 04, 2020,
We love the Caroline House. It was very charming and the location was absolutely perfect. VHKW did a great job. We would rent again for sure.

Jul 16, 2020,
House and location of the house is wonderful. We had our entire family there and were very comfortable. Only knock we had the whole time was that we had no tv service. Comcast I know is the one that dropped the ball so I have a hard time holding that against VHKW. I would stay at this house again everytime I visit Key West if we have several people going.

Jun 28, 2020,
The Caroline House was wonderful. I am extremely particular when renting vacation homes verses staying in luxury hotels and this property met my expectations. Perfect location, spacious for our group, and appropriately decorated for a high end property.

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