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COVID-19 INFO
Key West Time
February 8th
4:45am · 82°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.


tropical chill
special rates available

2BR 2BA

Mar 4- Mar 11
Weekly $2975


Standard Rates: $2165 - $4140 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. 


key west mile zero suite
special rates available

2BR 2BA

Feb 24- Mar 4
Nightly $675
Weekly $4150


Standard Rates: $2230 - $6030 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!


cockadoodle cottage on duval
special rates available

2BR 2BA

Jan 31 - Feb 4
Feb 11 - Feb 16
Feb 21- Feb 25
Mar 16 - Mar 19
Nightly $525



Standard Rates: $1895 - $4640 per week

2BR 2BA
Sleeps 4
Great for 2 Couples or Small Family
Jacuzzi Bath Tub
On Charming Upper Duval St.
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.'

 


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

3BR 2BA

Feb 10 - Feb 15
Feb 22- Feb 26
Mar 19- Mar 24
Nightly $685


Standard Rates: $2115 - $5625 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.


old town caribbean estate
New
special rates available

10BR 7.5 BA

Feb 6- Feb 9
Feb 28 - Mar 9
Mar 17 - Mar 23
Nightly $2600
Weekly $15000


Standard Rates: $10080 - $23420 per week

10 BR 7.5 BA - Sleeps 18 - 21
Heated Pool
7 BR Main House + 3 BR Guest House
Lush Tropical Gardens
Famous Historic Seaport neighborhood
Stroll to Duval St.

Spacious. Luxurious. Exotic. Old Town Caribbean Estate is a masterful combination of a classic Key West Victorian home with an exotic Caribbean-style guest house. A remarkable place for family and friends to stay together in a Key West weekly rental.


havana moon over duval
special rates available

2BR 2BA

Mar 11- Mar 14
Nightly $600


Standard Rates: $2190 - $5600 per week

2BR 2BA - Sleeps 4
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.

 


villa deja vu key west
special rates available

4BR 3BA

Feb 9 - Feb 17
Mar 17 - Mar 26
Weekly $6975
Nightly $1150

April 8- April 12
Nightly $1150


Standard Rates: $4345 - $10650 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.


tree tops
special rates available

2BR 2BA

Jan 31- Feb 8
Feb 19 - Feb 24

Nightly $550
Weekly $2800


Standard Rates: $2060 - $4170 per week

2BR 1BA - Sleeps 6
Overlooks large tropical garden with very large shared pool.
Boho style. Great value.

The Tree Tops Suite vacation rental is has a classic undying Key West charm that exudes a real down-island vacation feel. Approximately 750 square feet of living space offering an open floor plan joining the beamed ceiling living room and galley kitchen.


classic key west estate
special rates available

7BR 5.5BA

Feb 6- Feb 9
Nightly $2350

Feb 28 - Mar 9
Mar 17 - Mar 23
Nightly $2350
Weekly $12700


Standard Rates: $7310 - $20100 per week

7 BR 5.5 BA - Sleeps 14 - 16
Heated Pool
Lush Tropical Gardens
Famous Historic Seaport neighborhood
Stroll to Duval St.

Classic Key West Estate is a grand centurion home in the Historic Seaport neighborhood. It offers a spacious two-story Victorian home and a private pool side cottage. It's ideally located two blocks from the famous Historic Seaport. 


garden suite
special rates available

3BR 2BA

Jan 31- Feb 8

Weekly $3400
Nightly $650


Standard Rates: $2375 - $5170 per week

3BR 2BA - Sleeps 6
Situated in Gated Tropical Garden
Expansive covered porch
Very Large Pool.
Boho Style Decor
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.


key west wabi sabi
special rates available

4BR 3.5BA

Feb 9- Feb 11
April 8- April 11
April 18 - April 22
Nightly $1000

Mar 25 - April 1
Weekly $6475


Standard Rates: $4195 - $9700 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. More spacious than you may think. 2nd floor bedroom and private bath. Each bedroom has a bathroom. 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.


a tropical tradition
special rates available

3BR 2.5BA

Mar 2- Mar 8
Six nights $3675
Nightly $795


Standard Rates: $2265 - $5390 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.


the caroline house
special rates available

5BR 3BA

Feb 6- Feb 11
Feb 27 - Mar 2
Mar 5- Mar 9
Mar 26 - Mar 30
Nightly $1500


Standard Rates: $5345 - $13310 per week

5BR 3BA Classic Victorian Estate
Sleeps 10
3 BR Main House plus
2.5 BR Caribbean Bungalow
Heated Pool
In-ground 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.


heavenly hideout at rainbows end
special rates available

4BR 4BA

Jan 31- Feb 4
Nightly $975

Feb 9 - Feb 17
Feb 24- Mar 4
Weekly $5775
Nightly $975


Standard Rates: $4195 - $9700 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.

 


amelias hideaway
special rates available

4BR 4BA

Jan 31 - Feb 4
Mar 24- Mar 26
Apr 8- Apr 10
Apr 14- Apr 19
Nightly $975


Standard Rates: $4345 - $10650 per week

4BR 4BA - 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

2BR 2BA

Mar 9 - Mar 13
Mar 25- Mar 31
Nightly $685


Standard Rates: $2190 - $5500 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 ambience plus a private pool with bricked courtyard. Historic construction with original wood planked polished floors, vintage hand-hewn 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. 

 


cocos poolside retreat
special rates available

3BR 2.5BA

Feb 18- Feb 22
Mar 15 - Apr 1
Apr 8 - Apr 12
Weekly $3900
Nightly $650


Standard Rates: $2265 - $5390 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."


pavilion villa
special rates available

4BR 4BA

Mar 4- Mar 11
April 8- April 11
Weekly $6475
Nightly $1050


Standard Rates: $4345 - $10650 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. Close to shops, restaurants, museums, Mallory Square. 


vintage luxury cottage on duval
special rates available

1BR 1BA

Mar 17 - Mar 21
Mar 28 - Apr 1
Apr 8 - Apr 11
Nightly $650


Standard Rates: $1970 - $5400 per week

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

Vintage Luxury Cottage on DuvalRomantic hideaway. Completely hidden from the street! Private Heated Pool in charming bricked courtyard garden. Expansive covered porches. Nothing else like this extraordinary cottage in Key West.  


down island digs
special rates available

2BR 2BA

Mar 28- Apr 1
Nightly $650


Standard Rates: $2230 - $6030 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.

 

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