Key West Vacation Estates
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August 22nd
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Key West ~ Vacation Estates

Key West Estates - Large luxury privately owned classic mansion style homes that were originally built by early Key West landed gentry and maintained by wealth. Most are turn-of-the-century Victorian style homes with unique architectural details. Estate properties typically have five to eight bedrooms and can sleep 10 to 20 people.

View our exclusive Key West vacation rentals. Vacation Homes of Key West can help you find the perfect vacation rental for your next Key West vacation. Don't pay booking fees, save money by booking directly with VHKW today.

* PLEASE NOTE: Some properties displayed may not be available for rent due to other inquiries and pending reservations. 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. Please contact our office if you would like assistance. info@vhkw.com or 305-294-7358 ext. 1


seaport treasure estate

Standard Rates: $18000 - $26000 per month

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

A whole vacation experience for the entire family. Rent this 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!


bella grand premier

Standard Rates: $12000 - $21500 per month

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

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.”


classic key west estate
special rates available


Aug 25- Sept 6
Sept 9- Sept 20
Weekly $6225
Nightly $1500

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Standard Rates: $6375 - $12500 per week

7BR 5BA + 1 half BA - 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.


grande dame key west   the watson house
special rates available

Aug 22- Aug 29
Sept 2- Sept 24
Weekly $7550

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Standard Rates: $6900 - $13345 per week

7BR 7BA - Sleeps 14
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.


the caroline house
special rates available


Aug 25 - Aug 30
Nightly $975

Sept 11- Sept 28
Weekly $4950

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Standard Rates: $4500 - $9500 per week

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.


ultimate key west beach house  sunset key ~ vip

Standard Rates: $18000 - $26000 per month

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.