Key West Vacation Villas
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  • (305) 294-7358
Key West Time
April 18th
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Key West ~ Vacation Villas

Vacation Villas - Private 'free standing' single family homes which vary 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. 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

flower power house
special rates available

May 19 - June 1
weekly $5175
Nightly $1000

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Standard Rates: $3950 - $8325 per week

5-6BR (Sleeping Porch) - Sleeps 12+
Attached 1BR Cottage
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.

heavenly hideout at rainbows end
special rates available

May 27- June 1
June 8- June 13
Nightly $750

June 17- July 25
Weekly $3975

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Standard Rates: $3500 - $6925 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.


ocean view luxury villa

Standard Rates: $5400 - $7400 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..

key west sunset sojourn

Standard Rates: $10000 - $17000 per month

2BR + Office 3BA - Sleeps 6
Private Tropical Resort Island
Roof Top Viewing Deck
White Sandy Beaches
Oasis Swimming Pool

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. 

island elegance

Standard Rates: $5400 - $9500 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.

amelias hideaway
special rates available

May 12- May 15
Nightly $750

May 19- May 26
June 17- June 28
July 6- July 13
Weekly $4575

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Standard Rates: $3600 - $7600 per week

4BR 3.5BA - 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."


dancing palms villa
special rates available

May 11- June 30
Weekly $1975

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Standard Rates: $1925 - $3625 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.

key west wabi sabi
special rates available

April 20- April 26
Six nights $3500
Nightly $775

May 10= May 13
Nightly $700

June 23 June 29
July 6- July 20
Weekly $3975

Dec 24- Dec 28
4 nights $3500

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Standard Rates: $3500 - $6925 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. 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.

avant garde key west luxury home

Standard Rates: $4950 - $9700 per month

2BR 2.5BA
Sleeps 4
Classic Exterior Architecture
Upscale Minimalist Interior
Premier Heart of Old Town neighborhood
Private Heated Pool

Extraordinary upscale renovation. Traditional Key West architecture is flawlessly melded with a minimalist contemporary interior. Exotic and calming, this unique home offers all the best features of classic and modern island living.

villa deja vu key west
special rates available

April 17- April 24
weekly $5100
Nightly $875

May 11- May 18
weekly $4575

June 23- July 2
July 20- July 27
Weekly $4575

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Standard Rates: $3750 - $7600 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.

belle maison du port

Standard Rates: $13000 - $25000 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..

key west spa villa
special rates available

April 22- April 27
Nightly $800

June 9- June 13
Nightly $700

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Standard Rates: $3600 - $7600 per week

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

This proud 1890's 'cigar maker's cottage, just off Duval Street, has been lovingly transformed into a stylish 4 bedroom, 4 bathroom spa villa. Captivated by the uninhibited yet wonderfully elegant Key West island life-style, the designer created a fabulous balance of opposites.

tropical tranquility
special rates available

May 21- May 24
Nightly $1000

June 22- July 3
Weekly $5300

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Standard Rates: $3900 - $8675 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.


private pool garden villa

Standard Rates: $3200 - $5200 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.

pavilion villa
special rates available

Apr 29- May 2
May 29- June 1
May 6- May 9
May 12- May 16
Nightly $625

July 1- July 6
Five nights $3425

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Standard Rates: $3600 - $7600 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.

tropical luxury

Standard Rates: $3500 - $6700 per week

4BR 3BA - Sleeps 7-8
Heated Free-Form Pool - Sun Deck
Heart of Old Town Key West - Preferred Heart of Old Town neighborhood

Old-world charm meets modern tropical luxury in this wonderful historic island home. Built of original glistening heart pine from floor to ceiling, the interior rooms radiate a warm and magical feel. The grounds offer a classic front sitting porch, and generous size resort style back deck with custom free-form swimming pool.  

duval street fantasy resort villa

Standard Rates: $3750 - $7600 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. 

twice as nice on duval street
special rates available

June 15- June 30
Weekly $4275

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Standard Rates: $3750 - $7300 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.


the qm ~ quartermaster house key west

Standard Rates: $5500 - $10500 per month

3BR 2BA - Sleeps 6-7
Private Back Deck and garden
Shared Pool
Special Resort Amenities Gratis

Born in 1925, the Key West Quartermaster House may have found its way from the Bahamas, ‘lock stock and barrel’, during one of the most colorful points in Key West maritime history. Located in the Historic Seaport Neighborhood, today it offers all the comforts of home plus gratis resort amenities.

on hemingways rounds

Standard Rates: $4500 - $9300 per month

3BR 2BA - Sleeps 6
Private Spa Garden with Pool & Waterfall
1/2 block off Duval St.

On Hemingway's Rounds, is an inspired renovation of a classic 1930's ‘American Bungalow’ redone Key West style.  While the street side remains true to the original casual arts-and-crafts form, the interior now boasts an elegant simplicity that meets even the most discerning of modern tastes.


villa nouveau key west
special rates available

Apr 29- May 2
May 7- May 11
May 18- May 23
May 28= June 1
Nightly $800

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Standard Rates: $3600 - $7600 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.


key west dreamin
special rates available

May 30- June 5
Six nights $2550

June 30- July 1
Nightly $425

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Standard Rates: $2300 - $4925 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.

lazy iguana
special rates available

May 18- May 26
weekly $4300

June 2- June 7
June 21- June 24
Nightly $750

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Standard Rates: $3500 - $6700 per week

Large Private Swimming Pool
with Spacious Outdoor Cabana
4BR 3.5BA Main house plus Studio Cottage
Sleeps 8

During the months of May through January 2,  this genuine Key West combo of our Private Pool Garden Villa plus a classy private studio cottage that adjoins the property can be your very own get-away.

amandas dream suites

Standard Rates: $550 - $6500 per week

4-5BR (Den) 3BA - Sleeps 8-12
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.

governors retreat

Standard Rates: $5000 - $6700 per month

2BR 2BA - Sleeps 4
Serene setting - Large Lap Pool
Manicured Gardens
Old Town Key West Neighborhood -
The Meadows
Easy Stroll to Historic Seaport

A Key West luxury cottage in an idyllic retreat setting situated in a manicured garden and swimming pool. Perfectly Renovated and immaculate Key West neighborhood, known as The Meadows. Easy walk to Key West Historic Seaport. 

mediterranean caribbean villa

Standard Rates: $5500 - $9000 per month

2BR 2.5BA - Sleeps 4
Free-form heated pool - large sun deck
Manicured Tropical Gardens
Close to Higgs Beach and stylish White St.Gallery neighborhood

Tucked behind a breathtaking tropical garden wall and located along one of Key West's most desirable residential streets, this spectacular home reflects a dynamic blend of contemporary Mediterranean and Caribbean architectural design.

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