Key West ~ Vacation Villas

Below are Weekly & Monthly Rentals with no specified number of bedrooms and no specified arrival or departure date.

* PLEASE NOTE: Some properties displayed may not be available for rent due to other inquires and pending reservation. 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. However, if you are able to adjust your arrival or departure date we may be able to make it work. Please contact our office and let us do the work for you. info@vhkw.com or 305-294-7358 ext. 1

There is a minimum stay requirement of 30 days or 1 calendar month for monthly rentals. If you are having trouble finding an available rental please contact our office and let us do the work for you. info@vhkw.com or 305-294-7358 ext. 1


4BR 3BA - Sleeps 8-10
Heated Pool - Sun Deck
Lush Pool Garden
Just Off Upper Duval St.

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.

Weekly Rental Rates:
Winter - $5700 / wk - Shoulder - $5100 / wk - Summer - $4500 / wk

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villa deja vu key west

4BR 3.5BA - Sleeps 10
Heated Pool
Expansive Roof-Top Deck
Steps from Upper Duval St.

"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."

 

Weekly Rental Rates:
Winter - $5700 / wk - Shoulder - $5100 / wk - Summer - $4500 / wk

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amelias hideaway

4BR 3BA - Sleeps 10
Unique 2 Cottage Design
Heated Pool - Sun Deck
Deck + Balconies

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.

Weekly Rental Rates:
Winter - $5700 / wk - Shoulder - $5100 / wk - Summer - $4500 / wk

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pavilion villa

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.  

Weekly Rental Rates:
Winter - $5100 / wk - Shoulder - $4500 / wk - Summer - $4100 / wk

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tropical luxury

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

This one-of-a-kind island villa perfectly blends two charming historic cottages right into a little bit of Old Town Key West island heaven. Your own private tropical resort is the feeling you get when you enter the bricked courtyard.

Weekly Rental Rates:
Winter - $5700 / wk - Shoulder - $5100 / wk - Summer - $4500 / wk

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fantasy resort villa

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.

Weekly Rental Rates:
Winter - $5100 / wk - Shoulder - $4500 / wk - Summer - $4100 / wk

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key west wabi sabi

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.

Monthly Rental Rates:
Winter - $9000 / mo - Shoulder - $7500 / mo - Summer - $6000 / mo

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new property
the qm ~ quartermaster house key west

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

I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. 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.

 

Weekly Rental Rates:
Winter - $2500 / wk - Shoulder - $2150 / wk - Summer - $1850 / wk

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dancing palms villa

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.

Special Promotion ~ Extended Summer Rates ~ June 5 – Dec. 14, 2015

Monthly Rental Rates:
Winter - $8800 / mo - Shoulder - $6500 / mo - Summer - $5500 / mo

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on hemingways rounds

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.

Weekly Rental Rates:
Winter - $6500 / wk - Shoulder - $6050 / wk - Summer - $4950 / wk

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flower power house

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

A moden 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.

 

Weekly Rental Rates:
Winter - $5700 / wk - Shoulder - $5100 / wk - Summer - $4500 / wk

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villa nouveau key west

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

The cottage that grew into a villa ... This proud 1890's 'cigar maker's cottage' has been newly transformed into a stylish contemporary spa-garden 4 BR 4 BA Villa. Captivated by the weirdly wild yet wonderfully elegant Key West life-style, the owner created a fabulous balance of opposites.

Weekly Rental Rates:
Winter - $5700 / wk - Shoulder - $5100 / wk - Summer - $4500 / wk

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key west spa villa

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.

Weekly Rental Rates:
Winter - $3750 / wk - Shoulder - $3250 / wk - Summer - $2950 / wk

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key west dreamin

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.

 

Weekly Rental Rates:
Winter - $5700 / wk - Shoulder - $5100 / wk - Summer - $4500 / wk

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twice as nice

3BR 2BA - Sleeps 2-8
Outdoor Spa Room
Close to Higgs Beach

Strikingly set in the oft-missed Key West Beachside neighborhood, we find Island Elegance ~ Near the Beach, making a seriously smart curbside statement showing a tall white privacy wall topped with shimmering green louvers. Completely renovated in summer 2012, to modern luxury standards, this island home is a fabulous display of tropical-modern with the perfect touch of Caribbean-Colonial architectural detail.

Monthly Rental Rates:
Winter - $7250 / mo - Shoulder - $6250 / mo - Summer - $5250 / mo

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island elegance ~ near the beach

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.

 

Weekly Rental Rates:
Winter - $6850 / wk - Shoulder - $5900 / wk - Summer - $4800 / wk

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tropical tranquility

4-5BR (Den) 3BA - Sleeps 8-12
Bohemian Design and Decor
Large Shared Pool in Landscaped Garden
Expansive Porches
Easy Walk to Higgs Beach

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

Weekly Rental Rates:
Winter - $4800 / wk - Shoulder - $4450 / wk - Summer - $3650 / wk

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amandas dream suites

2BR 2BA - Sleeps 2-4
Heated Pool - Sun Deck
Historic Seaport neighborhood - Steps from the Harbor

Located steps from the Historic Seaport property is in one of the most charming and interesting Old Town residential neighborhoods of Key West. A low-key curb appeal makes a huge surprise when walk in and see the great room open to the fabulous swimming pool and deck in the back yard. 

Monthly Rental Rates:
Winter - $8500 / mo - Shoulder - $7200 / mo - Summer - $5550 / mo

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port side perfection

4BR 3BA + Library-Office
Swimming Pool
Spacious Private Back Deck and Courtyard
Center of Old Town Key West. Close to Dvual St.

Neatly situated between a fashionably narrow island street and a hidden lane, this "house-plus-guest-cottage" villa displays a West Indies design that smoothly melds a sophisticated British Colonial gracefulness with a carefree Caribbean flare. The overall effect both warms the heart and tickles the soul with a fanciful-folly-of-charm.

Monthly Rental Rates:
Winter - $10500 / mo - Shoulder - $8500 / mo - Summer - $8500 / mo

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key west indies

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

A luxury cottage in an idyllic retreat settng where you have the use of a manicured garden and swimming pool.  Perfectly Renovated and Immaculate Neighborhood.

Monthly Rental Rates:
Winter - $5800 / mo - Shoulder - $5100 / mo - Summer - $4600 / mo

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governors retreat

3BR 2.5BA - Sleeps 6
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.

Monthly Rental Rates:
Winter - $8000 / mo - Shoulder - $6300 / mo - Summer - $5250 / mo

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mediterranean caribbean villa

3BR (+Den) 3.5BA - Sleeps 6-7
Free-form heated pool - spacious sun deck
Close to Higgs beach in stylish White Street Gallery neighborhood

Live in the lap of luxury in this stunningly renovated Key West classic "Eyebrow House." An esteemed Key West renovation builder assembled a creative team of elite woodworkers, masons, local craftspeople, and an internationally known traveling artist sailor to execute his plans.

Monthly Rental Rates:
Winter - $9000 / mo - Shoulder - $7500 / mo - Summer - $6000 / mo

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