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info@vhkw.com
Key West Time
October 21st
4:36pm · 88°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.

** Trip Insurance Special: Promotional credit is currently available for purchasing trip insurance for stays between Aug 10 and Oct 20.
   2-3 Bedroom - $25 credit per night
   4-5 Bedroom - $50 credit per night
   6-7 Bedroom - $75 credit per night

There are no special deals at this time.


flower power house
special rates available


Nov 4- Nov 7
Nov 26- Nov 29
Nightly $800
Weekly $4900


Standard Rates: $3950 - $8225 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.


suite cottage key west
New
special rates available


Oct 29- Nov 3
Weekly $2400
Nightly $425


Standard Rates: $1900 - $4250 per week

2BR 2BA - Sleeps 4
Private Heated Pool
Private Sun Deck
Less than 1 Block from Duval St.

An artistic fusion of past meets present provides a decidedly refreshing and modern interpretation of a classic Key West style. On Simonton St., only one short street from the 500 block of Duval Street, on historic Simonton Street, this could be your perfect spot. Rent separate or with Villa Nouveau Key West or Grande Dame Key West - The Watson House estate.

 

heavenly hideout at rainbows end
special rates available


Oct 28- Nov 1
Nov 20- Nov 23
Nov 30- Dec 4
Dec 12- Dec 23
Weekly $3500
Nightly $700


Standard Rates: $3500 - $6825 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.

 


key west mile zero suite
special rates available


Oct 28- Nov 1
Nov 20 - Nov 23
Nov 30 - Dec 4
Dec 12- Dec 23
Weekly $2200
Nightly $400


Standard Rates: $2500 - $4000 per week

2BR 2BA - Sleeps 4
2nd FL Condo Suite plus private back deck on ground level
Downtown - 1 block off 500 block of Duval Street near Margaritaville
Private Heated Pool
Sun deck on ground level

When taking a selfie at the iconic Key West Mile Marker 0 just isn’t enough, now you can luxuriously live right next to this famous landmark ... in luxury and style!


tropical chill
New
special rates available

Nov 24-Dec 20
Weekly $1500

Dec 20- Dec 27
Weekly $1800


Standard Rates: $1500 - $2900 per week

2BR 2BA - Sleeps 4
Overlooks Tropical Swimming Pool Garden
Shared Heated Pool w/ Caribbean Cabana
Truman Annex Neighborhood
Gates lead to Ft. Zachary Taylor Beach, Truman Waterfront, and Downtown Old Town Key West

If you’re looking for a place to chill-out in the tropical warmth of Key West, this cottage-style flat is a wonderful place to relax and take a breather from everyday life. 


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

12/23-12/27
4 nights $1800


Standard Rates: $1800 - $3975 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.


cockadoodle cottage
special rates available

Nov 18- Nov 23
Nov 30 - Dec 3
Dec 10- Dec 16
Weekly $1800
Nightly $375

Jan 2- Jan 8
Jan 20- Jan 24
6 nights $1800
Nightly $400


Standard Rates: $1700 - $3275 per week

2BR 2BA
Sleeps 4 - 6
Great for 2 Couples or Small Family
Jacuzzi Bath Tub
Charming Upper Duval St. Neighborhood
1 minute walk to South Beach.

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.'

 


penthouse on duval
special rates available

Nov 24- Dec 1
Dec 15- Dec 19
Weekly $3400
Nightly $675

Jan 7- Jan 11
4 Nights $2400
Nightly $725


Standard Rates: $2900 - $6100 per week

4BR 4BA + (2 1/2 BA) - Sleeps 8
2 Kitchens
Entire 2nd + 3rd floors of the building
Porch overlooks Duval Street in the 700 Block.
Spacious deck in the back.
Adult Location

Perfectly staged on Duval Street Key West, this unique downtown Key West rental received a major renovation to become the  fabulous "Penthouse On Duval." Stroll to South Beach and Mallory Square. Plenty of room to spread out. Enviable Fantasy Fest location!  Mallory Square and the beach.


dancing palms villa
special rates available


Nov 20- Dec 1
Weekly $1825


Standard Rates: $1850 - $3525 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. 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.


amelias hideaway
special rates available

Oct 30- Nov 2
Nov 18- Nov 23
Dec 10- Dec 13
Nightly $700
Weekly $3700

Jan 3- Jan 9
Six Nights $4200
Nightly $900

Jan 13- Jan 18
5 nights $3500
Nightly $900


Standard Rates: $3600 - $7500 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."

 


caribbean cottage ~ duval street key west
special rates available

Nov 13- Nov 17
Nov 24- Nov 28
Dec 12- Dec 15
Nightly $400


Standard Rates: $1850 - $3850 per week

2BR 2BA
Sleeps 2 - 5
Charming Upper Duval Street
Private Heated Pool and Bricked Courtyard
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. 

 


island oasis garden home
New
special rates available

Oct 20- Oct 30
Fantasy Fest
weekly $1700

Nov 13- Nov 20
Weekly $1700


Standard Rates: $1675 - $3500 per week

2BR 2BA - Sleeps 2-4
1 Block from Duval Street
Oasis pool and hidden courtyard garden.
Private off-street parking

Just as you're inspired by an island oasis, so is this tropical island garden town home, cleverly hidden in the heart of Old Town Key West.

 

key west wabi sabi
special rates available


Oct 28 Nov 1
Dec 16- Dec 22
Weekly $3500
Nightly $700


Standard Rates: $3500 - $6825 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.


island brownstone
special rates available


Jan 9- Jan 19
weekly $2800
10 nights $3500


Standard Rates: $1900 - $3950 per week

2BR 2.5BA - Sleeps 4-6
Stroll to downtown Old Town Key West
Short walk to Fort Zachary Taylor Park and beach

An exclusive island style brownstone town home offers a dramatic and spacious layout with features and details that include extra high ceilings, artistic crown molding, lots of windows and French doors. It is perfectly nestled in Key West’s most prominent gated waterfront neighborhood known as ‘Truman Annex.’


villa deja vu key west
special rates available

Nov 18- Nov 23
Dec 9- Dec 13
Weekly $3850
Nightly $700

Dec 16- Dec 26
Weekly $5700
4 Nights $4400

Jan 12- Jan 16
Jan 23- Jan 26
4 nights $3000
nightly $900


Standard Rates: $3500 - $7500 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.


down island digs
special rates available

Nov 18- Nov 22
Dec 17- Dec 21
Weekly $2300
Nightly $400

Dec 28- Jan 5
Weekly $4000
Jan 12- Jan 18
6 nights $2500


Standard Rates: $1900 - $4250 per week

2BR 2BA
Sleeps 2 - 6
1/2 block off Duval Street
Traditional Key West Cottage-Style Charm
Hidden Large Back Yard Rare for Downtown Location
Private Manicured Pool-Side Garden.

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

 


classic key west estate
special rates available


Nov 26- Nov 29
Dec 11- Dec 21
Weekly $6000
Nightly $1200

Jan 5- Jan 9
Jan 16- Jan 19
Nightly $1200


Standard Rates: $5900 - $12100 per week

7BR 5BA + 1 half BA - 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.


key west spa villa
special rates available


Nov 24- Nov 28
Dec 15- Dec 19
Weekly $3900
Nightly $700


Standard Rates: $3600 - $7500 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.


grande dame key west   the watson house
special rates available


Nov 13- Nov 17
Nov 24- Dec 1
Dec 15- Dec 20
Nightly $1400
Weekly $7500


Standard Rates: $6750 - $13145 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.


vintage luxury cottage
special rates available


Nov 19- Nov 28
Dec 5- Dec 8
Dec 15- Dec 22
Weekly $1800
Nightly $350


Jan 6- Jan 12
Jan 23- Jan 26
6 nights $2300
Nightly $450

Jan 23- Jan 27


Standard Rates: $1800 - $3800 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 in hidden courtyard. "Best Kept  Key West Secret."


tropical tranquility
special rates available

Nov 14- Nov 18
Dec 15- Dec 22
Weekly $3900
Nightly $1100

Jan 5- Jan 9
Jan 23- Jan 26
4 nights $3900
Nightly $1100


Standard Rates: $3900 - $8575 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.

 


exclusive key west beach front
special rates available


Oct 22- Oct 26 fantasy fest
Nov 13- Nov 17
Dec 8- Dec 11
Nightly $400
Wekkly $2025

Jan 4- Jan 8
Nightly $475


Standard Rates: $1800 - $3975 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 ...

 


city island view
special rates available


Nov 12- Nov 15
Nov 24- Dec 1
Weekly $1550
Nightly $350

Jan 4- Jan 8

Nightly $400


Standard Rates: $1550 - $3600 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.


havana moon
special rates available

Nov 18- Nov 23
Nov 30- Dec 8
Weekly $1950
Nightly $425

Dec 23- Dec 26
$1800


Standard Rates: $1900 - $4075 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

Originally built in the late 1800’s as a 'cigar makers’ cottage, the authentic exterior of this turn-of-the-century cottage is protected by historic preservation rules and today stands renovated to form, to be proud and handsome. But the interior of Havana Moon, is an entirely different story. Inside the owners had creative license to redesign in order to bring the cottage upscale modern vacation standards, with all the luxurious accoutrements. The cottage also has a swimming pool and large deck for lounging and sunning. 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.

 


pavilion villa
special rates available

Jan 12- Jan 17
5 nights $3500
3/4 nights $3000


Standard Rates: $3600 - $7500 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

Dec 15- Dec 26
weekly $2100
4 nights $1700

Jan 7- Jan 11
Nightly $400


Standard Rates: $1500 - $3600 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.


a tropical tradition
special rates available


Oct 28- Oct 31
Nov 24- Nov 30
Dec 14- Dec 21
Weekly $1850
Nightly $375


Standard Rates: $1750 - $3770 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.


twice as nice
special rates available

Nov 18- Nov 23
Nov 30 - Dec 3
Weekly $3900
Nightly $800

Dec 23- Dec 26
$3000

Jan 2- Jan 8
6 nights $4300
Nightly $900


Standard Rates: $3600 - $7250 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.

 


cocos poolside retreat
special rates available


Nov 22- Dec 1
Dec 8- Dec 22
Weekly $1850
Nightly $375


Standard Rates: $1750 - $3770 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."


garden suite
special rates available


Nov 4- Nov 7
Nov 26- Nov 29
Nightly $400


Standard Rates: $1975 - $3500 per week

3BR 2BA - Sleeps 6
Garden Suite
Vacation Rental
Large covered porch steps to large tropicial garden with very large shared pool. Boho style. Great value.

The allure of the bohemian style Garden Suite vacation rental comes from its one-of-a-kind architectural design, the original wood it is built with, the fun decor, and its authentic Key West pool garden setting. Garden Suite offers over 1200 square feet of living space and features a large living room with cathedral ceilings.


the caroline house
special rates available


Oct 30 - Nov 5
Nov 16- Nov 27
Dec 4 - Dec 7
Dec 15- Dec 22
Weekly $4900
Nightly $1100


Standard Rates: $4500 - $9375 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


Oct 29- Nov 3
Nov 19- Nov 28
Dec 10- Dec 20
Weekly $4500
Nightly $750

Jan 21- Jan 24
Nightly $800


Standard Rates: $3600 - $7500 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 25- Nov 28
Dec 11- Dec 15
Nightly $450
Weekly $2500


Standard Rates: $2300 - $4875 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




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.

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