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October 16th
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Key West ~ Vacation Villas

What Are Vacation Villas? A vacation villa is a private 'free standing' single family home which varies in architectural style from traditional Key West Victorian to modern. Residences range from one to five bedroom dwellings.

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


uptown island luxury villa
New

Standard Rates: $3215 - $10980 per week

3BR 3.5BA - Sleeps 6
Steps from Upper Duval Street
Award-Winning Renovation
Private Heated Pool
Off-Street Parking

You’ll only wish you could live right here ‘happily ever after’ in this 3BR 3.5BA Uptown Island Luxury VillaIsland cottage charm meets up with modern elegance to mastermind this remarkable award-winning Key West poolside villa. 

 

 

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governors retreat
New

Standard Rates: $6500 - $16500 per month

3BR 2.5BA - Sleeps 6
Upscale renovation of Historic Home on Picturesque Lane
Private Swimming Pool w/ Sun Deck
1st & 2nd FL Covered Porches
Expansive Porch Room off Master BR
Off-Street Parking
1 Block Off Duval

Governor's Retreat is situated on a less-traveled lane that exudes sought after charm and character. Pictorial 1900’s historic home with upscale renovations and amenities. Exquisite and imaginative décor. Private pool and deck in fenced tropical garden. Multiple sitting porches in the front and back of the house. A block from the Hemingway Home and Museum.  

 

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on hemingways rounds
New

Standard Rates: $5200 - $11000 per month

2BR 2BA - Sleeps 4
Beautifully Renovated 1920 Bungalow
Private Swimming Pool & Sun Deck
Upscale Amenities
On Famous Whitehead St.
1 Block off Duval Street

On Hemingway's Rounds, is an inspired renovation of a classic circa 1920 American Bungalow redone Key West style. Private swimming pool garden and deck in the fenced back yard. Historic front porch with comfy chairs to relax and watch Key west go by. Interior design is imaginative and elegant. Less than one block from the Hemingway Home and Museum. 

 

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bohemian luxury villa
New

Standard Rates: $4700 - $9800 per month

2BR 2BA
Sleeps 4
Secluded & Quiet
Artistic Interior & Exterior Design
Large Private Deck off Great Room
Each Bedroom has a private fenced patio
Historic Secret Neighborhood of 6 homes w/
common pool garden

Completely hidden behind a tall-weathered garden gate, this 'Bohemian Luxury Villa' is part of a historic 'secret neighborhood' of 6 homes on one block. So discrete and tasteful in the exterior layout, no one can guess it is part of an exclusive garden compound. 

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key west spa villa

Standard Rates: $3900 - $13470 per week

4BR 4BA - Sleeps 8
Dipping Pool w/ Waterfall
Over-size Hot Tub
Private Sun Deck
Just off Upper Duval Street

Relax, Rejuvenate, Revive. When you rent this 'Key West Spa Villa,' outdoor lounging beside this unique spa garden deck puts a whole new spin on things. And when you're ready to take in Duval St., all you need to do is walk around the corner.

 

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villa nouveau key west
special rates available



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Standard Rates: $4270 - $13490 per week

4BR 4BA - Sleeps 8
Heated Pool
Private Sun Deck
Steps from Duval St.

A modern interior re-design has thoughtfully transformed a prosaic 'shot-gun' cottage it into the sophisticated 'L-Shape' 4 bedroom 4 bathroom pool-side courtyard Villa Nouveau. Fabulous downtown Key West location just off-Duval St. Rent separate or with Grande Dame Key West - 'The Watson House' estate.

 

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island elegance

Standard Rates: $4700 - $12500 per month

3BR 3BA - Sleeps 6
Timeless Historic Features
Split-bedroom Design
Spacious Front Porch
Tropical Landscaping
Bricked Private Driveway
Close to Key West Beaches on the South Shore

Channeling the island spirit in oft-missed mid-town, this home makes a classical curbside statement. Timeless craftsman-colonial architecture, lush mature tropical landscaping.Here you live away from the hubbub, yet close enough to beaches and Old Town. With many places to place a hammock, you may even find yourself making a new daily island ritual of swinging, reading, and sipping wine.

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villa deja vu key west
special rates available


Nov 20 - Nov 24

Nightly $850

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Standard Rates: $4060 - $13490 per week

4BR 3BA - Sleeps 8-10
Heated Pool - Sun Deck
Lush Pool Garden
1/2 Block Off Duval Street

We invite you to discover that incredible experience of Déjà vu ... you know, when you enter someplace for the very first time, and instantly you get that sense that you’ve been there before. When I first walked into this house it happened to me. My mind sparked and I felt an instant kinship with the surroundings.

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ocean view luxury villa

Standard Rates: $4280 - $17240 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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private pool garden villa
special rates available


Oct 15 - Oct 18
Nightly $725

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Standard Rates: $3120 - $9165 per week

3BR 2.5BA - Sleeps 6
Main House
Large Private Swimming Pool
with Spacious Outdoor Cabana
Close to Higgs Beach

Experience true tropical Key West living in this lush garden oasis home with large swimming pool and garden cabana located just one block from the beach. Easy bike ride to center of Old Town.

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flower power house
special rates available


Nov 14- Nov 22

Nightly $875
Weekly $4300

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Standard Rates: $4200 - $14760 per week

6BR- Sleeps 12+
Attached 1BR Cottage-style Suite
Overlooks Large Tropical Garden & Large Shared Pool.
Boho style. Great value.
Easy walk to Higgs Beach

Boho beautiful, the free-spirited presence of the Key West Flower Power House has much more in common with the 'real Key West'  than the shiny hotels around town. Off the beaten path but close to everything.

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dancing palms villa
special rates available



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Standard Rates: $1855 - $6870 per week

2BR 2BA - Sleeps 4
Manicured Tropical Swimming Pool Garden
Shared Heated Pool
Walk to Duval St. in 3 minutes

Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs. This is what you’ll experience as you make your entrance to this beautiful Bahamian ‘eyebrow’ style home, nestled away in private back corner of the small Old Town Key West gated community of Windward Park.

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key west wabi sabi
special rates available

Oct 18 - Oct 23

Weekly $3800
Nightly $800

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Standard Rates: $3500 - $12340 per week

4BR 3.5BA - Sleeps 8
Custom Interior Design
Heated Pool - Sun Deck
Steps from Duval St.

Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic cottage style island living. More spacious than you may think. 2nd floor bedroom and private bath. Each bedroom has a bathroom. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof.

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heavenly hideout at rainbows end
special rates available


Oct 16 - Oct 24

Nightly $800

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Standard Rates: $3500 - $12340 per week

4BR 4BA - Sleeps 8
Famous Mile 0 Location
1 block off Duval Street.
Custom Interior Design
Private Heated Pool
Sun deck on ground level

Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time.  But when you rent this Heavenly Hideout Key West penthouse, you’re spot on, and you can do exactly that.

 

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designer octagon house of key west

Standard Rates: $20000 - $35000 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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amelias hideaway
special rates available

Oct 19 - Oct 23


Nightly $850

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Standard Rates: $4060 - $13490 per week

4BR 4BA - Sleeps 10
Heated Pool
Expansive Roof-Top Deck
Steps from Upper Duval Street

"In-the-know" travelers who return to Key West love to choose the more elegant area of Upper Duval St. as their favorite area to stay ... "Amelia's Hideaway."

 

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belle maison du port

Standard Rates: $13000 - $29650 per month

3BR 3.5BA
Victorian Home + Private Guest Cottage
Situated in Private Gated Estate
Available from May through October
Large Private Heated Pool
Premier location - Hidden But Only Steps from Historic Seaport Boardwalk!

Extraordinary French Caribbean style Victorian home, Belle Maison du Port (Fine Harbor House), is available as a monthly vacation rental from May through November. Situated on the grounds of the Seaport Treasure Estate. It is comprised of a stunningly renovated 2–Story Victorian home, plus an adjoining one-bedroom guest cottage. Large private resort-style swimming pool with spacious sunning deck..

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tropical tranquility

Standard Rates: $4490 - $15365 per week

4BR 3.5BA - Sleeps 8
Heated Oasis Swimming Pool
Private Manicured Pool Garden
Little lane in the Heart of Old Town Key West

Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real.

 

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pavilion villa
special rates available



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Standard Rates: $4060 - $13490 per week

4BR 3BA - Sleeps 10
Unique 2 Cottage Design
Heated Pool - Sun Deck
Deck + Balconies
1/2 Block Off Duval Street

A Private Tropical Paradise... is the feeling you get when you enter the pavilion of this extraordinary award winning villa just a half block off Duval St. in Old Town Key West. Close to shops, restaurants, museums, Mallory Square. 

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duval street fantasy resort villa

Standard Rates: $4045 - $13470 per week

3BR 3BA - Sleeps 8
Just Off Upper Duval Street
Private Adjoining Cottages
with 2 Private Pools

Rare one-of-a-kind property, on Duval Street, yet hidden from the street. Two cottages jointed with a bricked courtyard and swimming pool create a secret resort residence. 

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twice as nice on duval street

Standard Rates: $3465 - $12960 per week

4BR 4BA Sleeps 8-10
Heated Pool
2 Sun Decks
2 Kitchens
On Upper Duval St. - 1 min. walk to South Beach

"Two is definitely better than One!" A rare set of early 1900's twin-cigar maker's cottages are both adorable and elegant and a perfect solution for a discerning group who want to lodge together in luxury but require maximum privacy.

 

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key west dreamin
special rates available

Oct 22 - Oct 25

Nightly $500

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Standard Rates: $2415 - $9595 per week

2BR 2BA - Sleeps 4-6
Heated Pool
Private Bricked Courtyard
Lush Landscaping

This Old Town Key West premier rental home offers all the luxury amenities, including a privateback yard pool garden. Situated in a charming Upper Duval neighborhood, a stroll through the neighborhood is to rendezvous with an important part of our island's rich cigar and rum history.

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amandas dream suites

Standard Rates: $3360 - $11590 per week

5BR (Den) 3BA - Sleeps 10-12
Bohemian Design and Decor
Large Shared Pool in Tropical Garden
Expansive Porches
Easy Walk to Higgs Beach

Originally built in 1938, this charming large wooden home has two full stories with deep porches which overlook the garden and shared swimming pool. The floor plan was redesigned with an exterior staircase so it can also be utilized as two separate units.

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