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COVID-19 INFO
Key West Time
November 27th
11:53am · 73°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.
   2-3 Bedroom - $25 credit per night
   4-5 Bedroom - $50 credit per night
   6-7 Bedroom - $75 credit per night
   11 Bedroom - $125 credit per night

There are no special deals at this time.


destination duval  a premier key west penthouse
New
special rates available

Dec 23 - Dec 26
Nightly $1100

Jan 15 - Jan 23
Weekly $5800
Nightly $1100


Standard Rates: $4130 - $12820 per week

4BR 4.5 BA - Sleeps 8
2450 SQ FT Premier 2-Level Penthouse
Uptown Duval Street Neighborhood
2 Private Covered Outdoor Porch Rooms
Shared Expansive Rooftop Deck and Heated Pool
Secured Covered Parking
Duval Square Vacation Rental

If you’re looking for a perfect Key West vacation rental that’s on Duval St, yet the ideal distance away from the bustle, you’re bound to love our– Destination Duval – A Premier Key West Penthouse. Strategically built on top of Duval Street, up here you’re in the cat bird’s seat, but at the same time invisible to the world below.


key west mile zero suite
special rates available

Dec 12 - Dec 19
Weekly $2200


Standard Rates: $2125 - $6155 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!


villa nouveau key west
special rates available

Dec 18 - Dec 26
Weekly $6750

Jan 2 - Jan 8
Six Nights $5560
Nightly $1200


Standard Rates: $4270 - $10100 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.

 


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


Standard Rates: $2030 - $5355 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 on duval
special rates available

Dec 19 - Dec 26
Weekly $2750

Jan 15 - Jan 19
Nightly $500


Standard Rates: $1575 - $4420 per week

2BR 2BA
Sleeps 4 - 6
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.'

 


villa deja vu key west
special rates available

Jan 8 - Jan 13
Nightly $975


Standard Rates: $4060 - $10100 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.


grande dame key west   the watson house
special rates available

Nov 27 - Dec 1
Nightly $1600


Standard Rates: $7560 - $17735 per week

7BR 7BA - Sleeps 14
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.


flower power house
special rates available

Jan 8 - Jan 13
Jan 17 - Jan 21
Nightly $1075


Standard Rates: $4200 - $11065 per week

6BR- Sleeps 12+
Attached 1BR Cottage-style Suite
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. Off the beaten path but close to everything.


key west wabi sabi
special rates available

Jan 2- Jan 6
Nightly $985

Jan 16 - Jan 24
Weekly $5700
Nightly $985


Standard Rates: $3500 - $9205 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.


havana moon over duval
special rates available

Nov 29 - Dec 2
Dec 7 - Dec 11
Nightly $450


Standard Rates: $1890 - $5315 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.

 


heavenly hideout at rainbows end
special rates available

Nov 28 - Dec 3
Nightly $750

Dec 12- Dec 19
Weekly $4100
Nightly $775

Jan 9 - Jan 15
Six Nights $4900
Nightly $885


Standard Rates: $3500 - $9205 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.

 


classic key west estate
special rates available

Nov 29 - Dec 2
Dec 9- Dec 13
Nightly $1400

Jan 4- Jan 8
Nightly $1775


Standard Rates: $6615 - $16610 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.


tree tops
special rates available

Jan 8 - Jan 13
Jan 17 - Jan 21
Nightly $485


Standard Rates: $1680 - $3955 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.


tropical tranquility
special rates available

Dec 4 - Dec 8
Dec 12- Dec 15
Nightly $900


Standard Rates: $4490 - $11535 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.

 


pavilion villa
special rates available

Jan 2- Jan 5
Jan 10 - Jan 14
Nightly $975


Standard Rates: $4060 - $10100 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. 


garden suite
special rates available

Jan 8 - Jan 13
Jan 17 - Jan 21
Nightly $525


Standard Rates: $1890 - $4720 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.


a tropical tradition
special rates available

Feb 2- Feb 5
Nightly $575


Standard Rates: $1995 - $5110 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.


down island digs
special rates available

Dec 12- Dec 15
Nightly $450


Standard Rates: $2100 - $5720 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.

 


key west dreamin
special rates available

Jan 11 - Jan 15
Feb 12 - Feb 16
Nightly $725


Standard Rates: $2415 - $6550 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.


cocos poolside retreat
special rates available

Jan 18 - Jan 25
Weekly $3550
Nightly $600


Standard Rates: $1995 - $5110 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."

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