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.
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Standard Rates: $16000 - $26750 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!
Months of June & Aug
available for a limited time through Mar 31 for a reduced price of
Standard Rates: $9000 - $25000 per month
4BR 3BA - Sleeps 8 - 10
Grand Luxury Estate Home
Historic Seaport Neighborhood
Heated Pool w/In-ground Jacuzzi
Entertain in grand style in the open living & formal dining room and outdoor pool-side chill-out room. Estate home built from original heart-pine wood, the interior is re-fit to be grand with polished Brazilian tigerwood floors and stunning mahogany open-beams on 12-foot ceilings. Built-in propane indoor/outdoor fireplace. Wrap around covered porches on the 1st and 2nd floor, and multi-level decks and covered porch create outdoor living spaces.
Standard Rates: $16000 - $26750 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.
Standard Rates: $10000 - $22000 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.”
Mar 28- Apr 1
Apr 10- Apr 18
Standard Rates: $6575 - $12800 per week
7BR 5BA + 1 half BA - Sleeps 12-14
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.
March 15- April 30
Standard Rates: $20000 - $30000 per month
4BR 4.5BA - Sleeps 8
Famous Iconic Victorian Estate
Extraordinary Designer Home
Expansive Resort-Style Gardens
Large Swimming Pool
Standing prominently in the sought-after Key West Historic Seaport Neighborhood, this iconic designer octagon Victorian house is often feaured in notable architectural publilcations. Purchased and restored by superstar designer Angelo Donghia in 1976, and purchased in 1981 by famous designer Calvin Klein, it raised the bar on historic home renovation in Key West. Today is stands as a phenomenal paradise home with luxury designer decor and 5-Star amenities. Truly an amazing historic and top-of-the-line place to stay in Key West.
Mar 28- Apr 3
Apr 11- Apr 22
Standard Rates: $7050 - $13700 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.
Mar 27 - Apr 4
Apr 11- Apr 16
Standard Rates: $4750 - $9700 per week
5BR 3BA Classic Victorian Estate
3 BR Main House plus
2.5 BR Caribbean Bungalow
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.