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Key West Time
November 24th
4:24am · 74°F
 
 

Vacation Rental Discounts and Special Rates

* PLEASE NOTE: The following special rates are a one time offer for the properties listed below. The rates and terms are subject to change without notice. For more information on terms and pricing please see our Rental Policies And Procedures. For faster response & more details please call 305-294-7358 ext. 1 or e-mail info@vhkw.com.

There are no special deals at this time.


seaport treasure estate
special rates available

January

Now available due to recent cancellation at a reduced rate of $21000


Standard Rates: $18000 - $26000 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!


flower power house
special rates available


Nov 25- Nov 29
Dec 10- Dec 14
Nightly $800


Standard Rates: $3950 - $8100 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

Nov 28 -Dec 7
Dec 11- Dec 23
Weekly $3500
Nightly $675

Jan 6- Jan 13
Jan 13- Jan 20
Weekly $4000


Standard Rates: $2900 - $6700 per week

4BR 4BA - Sleeps 8
Famous Mile 0 Location
1 block off Duval Street.
Custom Interior Design
Private Heated Pool starting August 1, 2017
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.

 


by the beautiful sea ~ a key west beach front condo
special rates available



Dec 16- Dec 26
Weekly $2700


Standard Rates: $1800 - $3900 per week

3BR 2BA - Sleeps up to 6
Private Ocean-View Terrace
Resort-Style Shared Pool

If you’re craving a Key West beach accommodation with a bona fide front-line view to the sea, you can instantly gratify this need with a stay in this pretty vacation rental condominium, By The Beautiful Sea.


bella grand premier
special rates available


Dec 1- Jan 2
$16500

Jan 2-Jan 31
$17500


Standard Rates: $12000 - $21500 per month

5BR + Den 5BA - Sleeps 12
Extraordinary swimming pool gardens
Famous Elizabeth St. in Historic Seaport Neighborhood
Stroll to Duval Street

Refined and Elegant. Displaying a perfected cosmopolitan flair, the designer has artfully intertwined a look-back into architectural history with a sophisticated contemporary Caribbean charm. Situated on renowned Elizabeth Street, in the historic seaport neighborhood of Old Town, this home is steeped in a colorful lore and seafaring history – so much so, it is sometimes referred to as “the pirate house.”


cockadoodle cottage
special rates available


Nov 30 - Dec 9
Dec 16- Dec 23
Weekly $1700
Nightly $325


Standard Rates: $1700 - $3225 per week

2BR 2BA (with Jacuzzi Bath Tub) - Sleeps 4-6
On Upper Duval St. - 1 min walk to South Beach.
Great for 2 couples or small family.

Key West cottage architecture has been time-tested in island life and culture in this infamous little wooden 'cigar maker's' cottage located on famous Duval Street, at the 'classier upper-end.'

 


key west sunset sojourn
New
special rates available

Dec 1- Jan 1
$11250


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. 


caribbean cottage ~ duval street key west
special rates available



Nov 24- Nov 29
Dec 13- Dec 23
Weekly $1900
Nightly $375


Standard Rates: $1850 - $3800 per week

2BR 2BA
Duval Street
Private Heated Pool and Bricked Courtyard
Sleeps 2-5
2 min. walk to South Beach.
Great for 2 couples + or small family

Just steps from Duval Street, this unique Key West cottage has an authentic Caribbean feel plus a private pool with bricked courtyard, with original wood planked polished floors, vintage hand-hewned beams, bright blue tile kitchen and Bahama style wooden window shutters. One of the oldest houses in Key West, exudes authentic charm with all the comforts of home. 

 


amelias hideaway
special rates available


Nov 25- Nov 28
Dec 10- Dec 22
Nightly $700
Weekly $3600

Jan 6- Jan 13
Weekly $4500
Jan 13- Jan 20
Weekly $4800


Standard Rates: $3600 - $7400 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."

 


exclusive key west beach front
special rates available

Dec 4 - Dec 10
Dec 17- Dec 22
Weekly $1900
Nightly $400






Standard Rates: $1800 - $3900 per week

2BR 3BA
Designer Condominium Overlooking Key West Ocean Sanctuary

You can see for miles & miles & miles ... South over the turquoise ocean the White Street Pier stretches out in the near distance. Fresh Caribbean Breeze, great white herons wade in clear shallows below, relaxing on the balcony, southern sunrise, full moon rising ...

 


dancing palms villa
special rates available

Dec 9- Dec 23
Weekly $1650.00

Jan 13- Jan 20
Weekly $2575


Standard Rates: $1850 - $3475 per week

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.

 


key west wabi sabi
special rates available


Dec 13- Dec 23
Weekly $3500
Nightly $700

Power boat races
Nov 9- Nov 13
Nightly $800


Standard Rates: $3500 - $6700 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.


down island digs
special rates available

Dec 2- Dec 6
Dec 13 Dec 16

Weekly $1900
Nightly $400


Standard Rates: $1900 - $4175 per week

2BR 2BA - Sleeps 2-6
1/2 block off Duval Street
Unique large private manicured pool-side garden.

Everything about "Down Island Digs" adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street.

 


vintage luxury cottage
special rates available



Nov 22- Dec 3

Weekly $1800
Nightly $375


Standard Rates: $1800 - $3725 per week

1BR 1BA - Sleeps 2-4
Duval Street
Hidden pool and courtyard.
2 min. walk to South Beach. Perfect couples retreat.

Vintage Luxury Cottage - An elegant Cottage with Private Heated Pool. "Best Kept Key West Secret."


villa deja vu key west
special rates available


Dec 2- Dec 9
Weekly $3600
Nightly $700

Dec 16- Dec 26
Weekly $5100


Standard Rates: $3500 - $7400 per week

4BR 3BA - Sleeps 8
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.


a tropical tradition
special rates available


Nov 25-Dec 7
Dec 10- Dec 14
Nightly $375
Weekly $1750


Standard Rates: $1750 - $3670 per week

3BR 2.5BA - Sleeps 6

A lush private tropical garden complete with large 40' X 16' swimming pool is the main focus of this unique island setting, and this traditional Key West town-home home is situated at the "pool-side" of the garden.


classic key west estate
special rates available



Dec 11- Dec 20
Nightly $1100
Weekly $5900


Standard Rates: $5400 - $12100 per week

7BR 5BA - Sleeps 12-14
Heated Pool
Lush Tropical Gardens
Famous Historic Seaport neighborhood
Stroll to Duval St.

Classic Key West Estate is one of the few grand centurion wooden estate homes plus pool-side cottage, with private deck and swimming pool, licensed to rent weekly in the Historic Seaport neighborhood. It is located on famous Fleming St. with beautiful curb side appeal.


grande dame key west   the watson house
special rates available

Nov 26- Dec 2
6 nights $5900
Nightly $1400

Jan 18- Jan 27
Weekly $8950


Standard Rates: $6750 - $12920 per week

7BR 7BA - Sleeps 16
Amazing Historic Luxury Mansion
Heated Pool - Private Sun Deck
Steps from Duval St.

This award winning renovation of a 3 - story Key West mansion is by far one the rarest private estate Key West rentals offered as a single-family vacation home available by the week. Steps from Duval Street.


havana moon
special rates available


Nov 22- Nov 29
Dec 20- Dec 23
Weekly 1900
Nightly $400

Jan 13- Jan 20
Weekly $2600


Standard Rates: $1900 - $4175 per week

2BR 2BA - Sleeps 4-6
Private Swimming Pool
On Upper Duval St. - 1 min. walk to South Beach.
Great for 2 couples or small family

Open the front door of this hand crafted Key West cottage and look south toward Havana Cuba and you'll catch a view of the ocean where the full moon rises with a soft salt southern breeze.

 


cocos poolside retreat
special rates available


Nov 27- Dec 19
Nightly $375
Weekly $1750

Jan 2- Jan 27
Weekly $2550


Standard Rates: $0 - $3670 per week

3BR 2.5BA - Sleeps 6-8

The artist-owner of this sun-lit pool-side town-home has created a delightful living space that welcomes you to an authentic tropical life-style in a unique Key West "pool garden compound."


tropical tranquility
special rates available


Jan 2- Jan 13
Weekly $5750


Standard Rates: $3900 - $8500 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.

 


city island view
special rates available

Nov 22- Nov 25
Dec 4- Dec 6
Dec 13- Dec 23
Weekly $1500
Nightly $350


Standard Rates: $1500 - $3500 per week

2BR 2.5BA - Sleeps 4
Best for Adults
Great view of Duval St. below in the 700 block.

Perched just above the fun and frolic of Duval Street you're sure to capture the "island beat" that stirs this tiny tropical island of Key West, Florida. Easy stroll to Mallory Square and South Beach.


private pool garden villa
special rates available

Jan 15- Jan 27
weekly $3700
nightly $650


Standard Rates: $3200 - $5100 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



Nov 27- Nov 30
Dec 13- Dec 16
Dec 20- Dec 23
Weekly $3600
Nightly $700

Jan 6- Jan 13
Jan 13- Jan 20
Weekly $4800


Standard Rates: $3600 - $7400 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.


starlight siesta
special rates available


Nov 22- Nov 25
Dec 4- Dec 6
Dec 13- Dec 16
Weekly $1500
Nightly $350

Jan 15- Feb 3
Weekly $1900


Standard Rates: $1500 - $3500 per week

2BR 2.5BA - Sleeps 4
Private back deck at end of lane off Duval St. in the 700 block. Island urban. Best for Adults.

Cleverly staged in the island's city center, this downtown Key West rental is located in the 700 block of Duval Street, at the end of a narrow urban 'dead end' lane. Completely hidden from view on the 2nd and 3rd levels, spacious and creative renovation. Easy stroll to Mallory Square and South Beach.


twice as nice
special rates available



Dec 16- Dec 23

Weekly $3600
Nightly $700


Standard Rates: $3600 - $7400 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 caroline house
special rates available


Nov 25- Nov 30
Dec 3- Dec 7

Weekly $4500
Nightly $1000

Jan 6- Jan 27
Weekly $5900


Standard Rates: $4500 - $9250 per week

5BR 3BA Classic Victorian House - Sleeps 10
Plus 2BR 1/2 story Caribbean Bungalow
Heated Pool
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.


villa nouveau key west
special rates available


Dec 1- Dec 6
Dec 13- Dec 19
Weekly $3900
Nightly $750

Jan 2- Jan 13
Weekly $4800


Standard Rates: $3600 - $7400 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

Nov 22- Nov 25
Weekly $1900
Nightly $400

12/2-12/12
Weekly $2100


Standard Rates: $2300 - $4800 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


Nov 25- Dec 6
Nightly $650
Weekly $3500

Dec 30- Jan 6
Weekly $4900

Jan 6- Jan 12
Nightly $750
Six nights $3800


Standard Rates: $3500 - $6600 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.

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