Key West Time
April 3rd
2:56am · 81°F
April 3rd
2:56am · 81°F
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. 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
Standard Rates: $8,500 - $26,897 per month
3BR 4BA
Sleeps 6
Private Pool
Located in the Heart of Old Town
3 BR 3.5 Baths
May 1- May 31
Monthly $12250
Standard Rates: $12,000 - $34,097 per month
3BR 4BA
Sleeps 6 - 8
Luxury Vacation Villa
Private Pool and Spa
Located in the Heart of Old Town
Beautifully furnished, complete with modern amenities and coastal charm. Each bedroom offers ample space and privacy, with en-suite bathrooms ensuring convenience for all guests. Fully-equipped kitchen, perfect for entertaining.
5BR 5.5Baths
Apr 1- May 31
Monthly $22000
Standard Rates: $23,000 - $40,345 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.
Standard Rates: $28,400 - $59,483 per month
7BR 7.5BA - Sleeps up to 14
2 heated swimming pools
Premier Street in Center of Old Town
2-Story Guest House + 2-Story Main House and separate 2BR cottage
5-Star rental compound Ideal for extended families or a group of friends.Revel in luxuy while you relax, unwind, and reconnect with plenty of room to spread out. Property includes: two private swimming pool gardens and enjoy three fully equipped upscale kitchens. Grill on a unique secluded BBQ porch, workout in a private home gym, and at your fingertips is a Steinway piano! Three off-street parking spaces.Off-the-beaten path yet just three streets from mid-Duval St.
Standard Rates: $5,925 - $10,760 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
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..
10BR 7.5 BA
Mar 22 - Apr 3
Apr 6- Apr 12
Apr 20 - Apr 24
Nightly $2500
Weekly $13000
Standard Rates: $12,390 - $25,975 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.
Standard Rates: $18,500 - $36,000 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.
4BR 4BA
May 1 - May 31
Monthly $19000
Standard Rates: $18,000 - $36,000 per month
4BR 4BA
Sleeps 8
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.
Standard Rates: $50,000 - $87,000 per month
5BR + Den 7BA - 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.
7BR 5.5BA
Mar 22- Apr 3
Apr 6- Apr 12
Apr 20 - Apr 24
Nightly $2300
Weekly $11000
Standard Rates: $9,190 - $25,975 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.
5BR 3BA
Apr 2- Apr 11
Weekly $7500
Nightly $1400
Standard Rates: $6,645 - $13,710 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.
