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August 13th
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Key West ~ Vacation Estates

What Are Key West Estates? Key West Estates are 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. 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. or 305-294-7358 ext. 1

designer octagon house of key west
special rates available


Aug 15- Oct 31


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Standard Rates: $25000 - $40000 per month

4BR 4.5BA - Sleeps 8
Famous Iconic Victorian Estate
Extraordinary Designer Home
Expansive Resort-Style Gardens
Large Swimming Pool
Wrap-around Verandahs

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.

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bella grand premier estate

Standard Rates: $22000 - $38800 per month

5BR 5.5BA - Sleeps 10
Grand Luxury Estate on 7,500 Sq Ft Lot
2-Story Guest House + 2-Story Main House
Deluxe Zen-Garden Pool with Pool Bridges
Steinway Upright Piano
Premier Street in Center of Old Town
Gated and Private
5-Star Quality Experience

Deluxe Old Town Key West estate with a new twist on history. Premier custom design reflects the historic neighborhood, while reinventing the Key West luxury lifestyle. Zen-garden swimming pool, trickling tiled waterfalls and a spa. Wide stone bridges built over the pool sleekly connect the houses together. A remarkable home to experience with family and friends. 

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old town caribbean estate
special rates available

10BR 7.5 BA

Aug 22 - Aug 25
Aug 29 - Sept 1
Sept 5 - Sept 8
Sept 11 - Sept 16
Sept 20 - Sept 30
Weekly $9800
Nightly $1700

Dec 23 - Dec 26

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Standard Rates: $10080 - $22200 per week

10 BR 7.5 BA - Sleeps 18 - 21
Heated Pool
7 BR Main House + 3 BR Guest House
Lush Tropical Gardens
Famous Historic Seaport neighborhood
Stroll to Duval St.

Spacious. Luxurious. Exotic. Old Town Caribbean Estate is a masterful combination of a classic Key West Victorian home with an exotic Caribbean-style guest house. A remarkable place for family and friends to stay together in a Key West weekly rental.

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private island key west beach house  sunset key ~ vip

Standard Rates: $18000 - $28000 per month

3BR 4BA Sleeps 6
Epic View from the Pool to the Beach
Private Tropical Resort Island
Garden Connects with White Sandy Beaches

Epic views from the house, to the pool, to the beach. Grand traditional beach house on the private island of Sunset Key. Far enough away that life slows down. White sandy beaches, turquoise ocean, palm trees rustling, birds twittering - peacefulness. 5-Star Resort amenities at your service.

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seaport treasure estate

Standard Rates: $17000 - $31750 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!

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ocean view luxury villa

Standard Rates: $4280 - $10600 per week

3BR 4BA - Sleeps 6-8
Ocean View / Sun Deck
Private Heated Pool
Key West Truman Annex Neighborhood
Short Walk to Beach and Key West Waterfront Park Amphitheater
Pet Friendly

Gorgeous Old Town Key West Ocean View Luxury Home in immaculate gated neighborhood! Holding an enviable spot in Key West’s gated community of Truman Annex, this classic home offers an open water view, easy beach access, and is a short walking distance to Duval Street and downtown Old Town Key West..

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key west sunset sojourn

Standard Rates: $10600 - $26625 per month

3BR + Media Room 4BA
Sleeps 6
Private Swimming Pool w/ fenced gardens
Private porches off each BR
Private Roof-Top Lookout Deck
White Sandy Beaches
Private Tropical Resort Island

Imagine the ultimate Key West dream home that feels like a faraway oasis - where you can watch crowning tropical sunsets from a private rooftop deck. Someplace truly extraordinary, elegant yet also comfortable – a sojourn on a private island surrounded by sparkling turquoise waters and balmy breezes. 

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classic key west estate
special rates available

7BR 5.5BA

Aug 22 - Aug 25
Aug 29 - Sept 1
Sept 5 - Sept 8
Sept 11 - Sept 16
Sept 20 - Sept 30
Weekly $7500
Nightly $1500

Dec 23- Dec 26

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Standard Rates: $7310 - $20100 per week

7 BR 5.5 BA - Sleeps 14 - 16
Heated Pool
Lush Tropical Gardens
Famous Historic Seaport neighborhood
Stroll to Duval St.

Classic Key West Estate is a grand centurion home in the Historic Seaport neighborhood. It offers a spacious two-story Victorian home and a private pool side cottage. It's ideally located two blocks from the famous Historic Seaport. 

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the caroline house
special rates available


Aug 14 - Aug 17
Aug 25 - Sept 8
Sept 12 - Sept 19

Weekly $6450
Nightly $1175

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Standard Rates: $5345 - $12625 per week

5BR 3BA Classic Victorian Estate
Sleeps 10
3 BR Main House plus
2.5 BR Caribbean Bungalow
Heated Pool
In-ground 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.

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