Key West ~ Vacation Estates

Below are Weekly & Monthly Rentals with no specified number of bedrooms and no specified arrival or departure date.

* PLEASE NOTE: Some properties displayed may not be available for rent due to other inquires and pending reservation. Please contact our office to be sure of availability. info@vhkw.com or 305-294-7358 ext. 1

There are no properties available that fit all of your search options. However, if you are able to adjust your arrival or departure date we may be able to make it work. Please contact our office and let us do the work for you. info@vhkw.com or 305-294-7358 ext. 1

There is a minimum stay requirement of 30 days or 1 calendar month for monthly rentals. If you are having trouble finding an available rental please contact our office and let us do the work for you. info@vhkw.com or 305-294-7358 ext. 1


6BR 6.5BA - Sleeps 12
Luxurious Estate ~ 2 Houses plus Guest Cottage = Private Residential Resort
Gated and Grand
Premier Historic Seaport location!

A whole vacation experience for the entire family. Rent the whole estate and live in luxury in the most requested Historic Seaport location in Key West. Three historic dwellings are seamlessly joined to become one private luxury Key West rental estate. A combination of unique design elements impart that elusive je ne sais quoi of island architectural history. Rent the best of Key West!

Monthly Rental Rates:
Winter - $25000 / mo - Shoulder - $18000 / mo - Summer - $18000 / mo

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new property
seaport treasure estate

5BR + Den 5BA - Sleeps 12
Extraordinary swimming pool gardens
Famous Elizabeth St. in Historic Seaport neighborhood
Stroll to Duval St.

Refined and Elegant. Displaying a perfected cosmopolitan flair, the designer has artfully intertwined a look-back into architectural history with a sophisticated contemporary Caribbean charm. Situated on renowned Elizabeth Street, in the historic seaport neighborhood of Old Town, this home is steeped in a colorful lore and seafaring history – so much so, it is sometimes referred to as “the pirate house.”

Monthly Rental Rates:
Winter - $21500 / mo - Shoulder - $12000 / mo - Summer - $12000 / mo

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new property
bella grand premier

7BR 5BA - Sleeps 12-14
Heated Pool
Lush Tropical Gardens
Famous Historic Seaport neighborhood
Stroll to Duval St.

Classic Key West Estate is one of the few grand centurion wooden estate homes plus pool-side cottage, with private deck and swimming pool, licensed to rent weekly in the Historic Seaport neighborhood. It is located on famous Fleming St. with beautiful curb side appeal.

Weekly Rental Rates:
Winter - $8700 / wk - Shoulder - $7300 / wk - Summer - $6350 / wk

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as seen on house hunters on vacation hgtv
classic key west estate

7BR 7BA - Sleeps 16
Amazing Historic Luxury Mansion
Heated Pool - Private Sun Deck
Steps from Duval St.

This award winning renovation of a 3 - story Key West mansion is by far one the rarest private estate Key West rentals offered as a single-family vacation home available by the week. Steps from Duval Street.

Weekly Rental Rates:
Winter - $10475 / wk - Shoulder - $9150 / wk - Summer - $7950 / wk

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grande dame key west

5BR 3BA Classic Victorian House - Sleeps 10
Plus 2BR 1/2 story Caribbean Bungalow
Heated Pool
Jacuzzi
Large Private Garden

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.

Weekly Rental Rates:
Winter - $7500 / wk - Shoulder - $6200 / wk - Summer - $5200 / wk

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the caroline house

5BR + Den 6BA - Sleeps 10-12
Private Tropical Resort Island
Front Line Ocean Views
White Sandy Beaches
Custom Fantasy Swimming Pool w/ Waterfalls

Sit back, relax, and choose your favorite mesmerizing view from one of the magnificent private decks on this private island property, 500 yards from the ''main island' of Key West.  Unhurried sunrise, serene sunset, warm turquoise waters, and white sandy beaches – from any direction, it’s divine.

Monthly Rental Rates:
Winter - $25000 / mo - Shoulder - $18000 / mo - Summer - $18000 / mo

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new property
ultimate key west beach house  sunset key ~ vip

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