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.


the meeting point   key west
special rates available

7/30-8/11
weekly $12450


Standard Rates: $10350 - $20170 per week

11BR 11BA - Sleeps up to 24
2 heated swimming pools (1 with Spa Jets)
Steps from the 500 block of Duval Street
3-story historic Victorian home plus new 4 BR villa

"Let's stay together ... for a week or more." Start calling your family and make a plan. If you’re looking for luxury and plenty of room, The Meeting Point Key West is the grandest vacation rental licensed to rent weekly in Key West, both in stature and style. 7 BR 7 Full BA elegant Victorian Mansion plus 4 BR 4 Full BA luxury villa. 


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

July 8-July15
Aug 11- Aug 18
weekly $2100


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.


dancing palms villa
special rates available

July 8 - August 5
Weekly $1850.00


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.

 


amelias hideaway
special rates available


June 18-June 22
nightly $600

June 29- July 8
July 15- July 22
weekly $4000
Nightly $800


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."

 


cockadoodle cottage
special rates available

June 14 - June 17
Aug 12-Aug 26
July 3-July 13
July 20-July 27
weekly $1900
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 wabi sabi
special rates available

June 23- June 27
July 15- July 25
Aug 15- Aug 24
weekly $3900
nightly $700


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.


penthouse on duval
special rates available

June 18- June 23
July 3 - July 6
July 9 - July 20
weekly $3400
nightly $675


Standard Rates: $2900 - $6000 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.


caribbean cottage ~ duval street key west
special rates available

June 20- June 24
June 30 - July 3
July 15 - July 21
weekly $2100
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. 

 


villa deja vu key west
special rates available

June 21- June 24

July 1 - July 9
July 18 - July 22
Aug 12 - Aug 23
weekly $3900
nightly $750


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.


exclusive key west beach front
special rates available

Aug 12 - Aug 26
weekly $2100
nightly $450


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 ...

 


key west spa villa
special rates available

July 2 - July 13
July 16- July 22
July 29 - Aug 10
Aug 13 - Aug 27
weekly $3900


Standard Rates: $3600 - $7400 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.


down island digs
special rates available

July 17 - July 22
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.

 


tropical tranquility
special rates available

July 15 - July 22
Aug 12 - Aug 19

weekly $4800
nightly $1000


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.

 


vintage luxury cottage
special rates available

July 7-July 22

weekly $1950
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."


private pool garden villa
special rates available

July 5 - July 20

weekly $3300


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.


a tropical tradition
special rates available

July 22- July 25
nightly $375


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


June 24- June 28
July 15- July 19
July 23- July 26
Nightly $1100


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.


tropical luxury
special rates available

June 27- July 1
nightly $600


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.  


grande dame key west
special rates available

7/30-8/11
weekly $7950


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

June 14- June 17
July 10- July 13
July 20- July 27
Aug 12- Aug 26
weekly 2150
nightly $450


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.

 


twice as nice
special rates available

July 20 - July 27
Aug 12- Aug 26

weekly $4100


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.

 


starlight siesta
special rates available

June 18- June 23
July 3- July 6
July 9 - July 20
Aug 15- Aug 25
weekly $1750
Nightly $350


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.


key west dreamin
special rates available


July 9- July 14
Aug 12- Aug 26
$450/night
Weekly $2550


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.


the caroline house
special rates available

July 9 - July 22
Aug 15- Aug 30
weekly $5200


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.


lazy iguana
special rates available

June 17- June 21
July 5- July 20

nightly $650
weekly $3900


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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