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. email@example.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. firstname.lastname@example.org or 305-294-7358 ext. 1
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!
Standard Rates: $15000 - $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: $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.
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.”
Dec 13- Dec 20
Jan 4- Jan 8
Jan 13- Jan 16
Feb 2- Feb 8
Six nights $8600
Standard Rates: $6375 - $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.
Nov 21- Nov 24
Dec 1-Dec 4
Dec 9- Dec 21
Jan 4- Jan 8
Jan 12- Jan 17
Jan 21- Jan 28
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.
Dec 28- Jan 3
Six nights $8000
Feb 2- Feb 10
7 or 8 nights available
Standard Rates: $4650 - $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.
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.