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info@vhkw.com
Key West Time
June 16th
4:20am · 84°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 hideaway
special rates available

2BR 1.5BA

July 7 - Aug 31

Monthly $4700



Standard Rates: $4500 - $9675 per month

2BR 1.5BA
Sleeps 2 - 4
Limited Edition 2-Story Condo
2 Streets from Historic Seaport
Private Porches and Courtyard Garden
Hidden from View in Heritage Building

Magic happened when this Key West wooden heritage building was redesigned. Now offers limited-edition condominiums. A case in point is this 2BR 1.5BA Seaport Hideaway. Architecturally intriguing. Epic historic atrium stairwell. Masterfully tucked away on Fleming Street. A special residence ideally located 2 short blocks from the docks, at the Key West Historic Seaport neighborhood.

 


elegant key west tree house
special rates available

2BR 1BA

June 14- July 31

Monthly $4500


Standard Rates: $4200 - $8025 per month

2BR 1BA
Overlooks large historic Meditation Garden
Quiet living
One Set of Stairs
Close to Higgs Beach

Discretely built back off the street to quietly overlook an historic tropical garden, this Elegant Key West Tree House, encompasses the entire 2nd floor of a beautifully renovated 1930’s building. Perched among mature tropical trees, the 1200 square foot 2nd floor flat is situated on a quiet road in the exclusive Old Town Casa Marina neighborhood. With a wide wooden covered porch spanning the front of the house, every room still has the original casement windows providing a fabulous look-down view of different garden scenes.


serenity now
New
special rates available

2 BR 2.5 BA

Monthly

July 13 - Aug 31

Monthly $6200


Standard Rates: $6200 - $17100 per month

2BR 2.5BA - Sleeps 4
Located in Small Gated Enclave w/in Truman Annex Neighborhood
Large Shared Heated Pool and Jacuzzi
Private Gate is Steps to Downtown Old Town
Short stroll to Truman Waterfront Park and Ft. Zacharay Taylor Beach

Close your eyes for a moment and take a deep breath ...  Now imagine yourself on an extraordinary Old Town Key West vacation. This luxury townhome vacation rental stands on a serene street, tucked in a tiny enclave called Key West Porter Court. A bit of a secret, it’s nicely hidden within the stunning neighborhood of Truman Annex where the gated grounds are park-like and immaculate. It’s as if you’re in a dream.


sunset sonnet luxury villa
New
special rates available

2BR 3BA

Aug 1 - Sept 30

Monthly $9400


Standard Rates: $9500 - $21300 per month

2BR + Office 3 BA
Sleeps 4
Private Roof Top Viewing Deck
White Sandy Beaches
Garden Oasis Swimming Pool
Private Tropical Resort Island

Sunset Sonnet Luxury Villa provides an exclusive private island experience with all the amenities of resort living. A colonial - modern 2-story private luxury home. Wrap around porches overlooking pool gardens. Manicured beaches, tennis, award winning restaurant close by, 5-Star amenities. Experience the peace of  living on a tiny island with no cars. To stay on Sunset Key is to be in secluded surroundings, just a 15-minute ferry ride from downtown Key West.

 


rooftop renaissance
New
special rates available

1 BR 2 BA

Aug 1- Sept 30

Monthly $4500


Standard Rates: $4900 - $9150 per month

1BR 2BA
Sleeps 2 - 4
Stunning 2-Story Luxury Condo
Hidden in a Heritage Victorian
Private open-air deck
Shared Zen-pool and spa
2 Streets from Historic Seaport

Rooftop Renaissance falls into a unique architectural category of Heritage Victorian - Meets Modern Luxury. This one-of-a-kind monthly rental is situated on the 2nd and 3rd level of a historic Victorian house on Caroline Street. An exquisite 1BR 2BA luxury accommodation, it was redesigned to offer all the accoutrements of a 5-Star condominium.

 


admirals gold private key west luxury villa
New
special rates available

4 BR 3.5 Baths

July 5- July 12
Weekly $5500




Standard Rates: $5420 - $12570 per week

4BR 3.5BA - Sleeps 8
Located in Truman Annex Neighborhood
Waterfront Park Amphitheater
Shared Heated Pool
Short Walk to Beach

Elegant tropical luxury home with impeccable attention to detail. Situated in Key West’s prestigious gated community of Truman Annex! Short walk to Fort Zachary Taylor and Truman Waterfront. Just out the gate to downtown Old Town Key West and Duval Street.


little digs key west
special rates available

1BR 1BA

June 14- July 31

Monthly $4,100


Standard Rates: $3600 - $6000 per month

1 BR 1 BA
Sleeps 2 - 3
Luxury Interior Upgrades
Solares Hill Neighborhood
Center of Old Town
5 Minute Walk to Duval Street

Diminutive in size but huge in style, Little Digs Key West, authenticates how ‘big things’ really do happen in small spaces. Spacious design. A complete luxury makeover of this 1933 historic cottage. It sits in proud harmony with other historic residential cottages, on a narrow one-way lane in the middle of Old Town Key West. 


key west poolside loft
special rates available

2BR 2BA

Monthly

Sept 1- Sept 30

Monthly $4700


Standard Rates: $4725 - $9200 per month

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

You know that adage … An unexpected turn can lead to hidden treasures. If there were ever a place that meets that description, it's this 2BR 2BA Key West Poolside Loft. Cleverly tucked away, here you’re in a unique loft-style Key West cottage, with a private deck and beautiful down-look poolside view.


hidden story book cottage
special rates available

1BR 1BA

June 14- July 31

Monthly $3,975


Standard Rates: $3700 - $6175 per month

1 BR 1 BA
Sleeps 2 - 3
Free-Standing Story-Book Cottage
Gorgeous Interior Upgrades
On a Hidden Walking Path
5 Minute Walk to Duval Street

Tucked away down a short walking path in the Center of Old Town Key West, this precious 1BR 1BA Hidden Story-Book Cottage is completely hidden from the street. Comfortable as it is adorable, it even offers a fenced in yard. Perfect for one or two people, here you can set up home and live as a local for a month or more - or settle in to work remotely.

 


villa corazon
New
special rates available

3BR 3.5BA

June 14 - July 31

Monthly $ 6850


Standard Rates: $7900 - $17500 per month

3BR 3BA
Private garden with heart-shaped pool
Luxury renovation with upscale furnishings
Private Guest Cottage in Garden
Casa Marina Neighborhood
Close to Higgs Beach

There’s lots to love about the luxurious 3BR 4BA Villa Corazonit even has a heart shaped pool. Experience ultimate resort style living in this private home retreat. A perfect pairing of a renovated Key West gingerbread cottage with an elegant free-standing cottage that are seamlessly joined with a tropical pool-garden.The interior is a harmonious sweet spot between modern aesthetics and laid-back Caribbean. 


tropical chill
special rates available

2BR 2BA

June 14 - June 30
Weekly $2100


Standard Rates: $2230 - $4260 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

May 29 - June 6
June 14 - June 30

Weekly $2900
Nightly $575


Standard Rates: $2580 - $6200 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

June 13 - June 17
June 22- July 1

Nightly $475
Weekly $2500





Standard Rates: $2095 - $4760 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.'

 


butterfly garden
special rates available

1BR !BA

June 14- July 31

Monthly $3900


Standard Rates: $3975 - $6300 per month

1BR 1BA - Sleeps 1-2
Historic meditation garden.
Quiet Living Exclusive Casa Marina neighborhood.
Close to Higgs Beach

Completely hidden from the street, this historic Butterfly Garden flat provides you with two private entrances off the large gated meditation garden. A private covered sitting porch outside your front door beckons you to sit in the freshness of the garden and watch for the butterflies.


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

3BR 2BA

June 19- June 23

Nightly $525
Weekly $2500


Standard Rates: $2580 - $5775 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.


exclusive key west beach front
special rates available

2BR 3BA

July 7 - July 19

Weekly $2550


Standard Rates: $2530 - $5775 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 ...

 


sweet sunshine garden flat
special rates available

2BR 1BA

July 2- July 13
Weekly $1800


Standard Rates: $1800 - $3675 per week

2BR 1BA - Sleeps 4
Truman Annex Neighborhood
Steps to Truman Waterfront Park
Shared Heated Pool w/ Caribbean Cabana
2 Blocks from Duval Street
10 minute walk to the waters' edge of Ft. Zachary Taylor Beach

Sweet Sunshine Garden Flat is perfectly situated for a week near the beach and downtown Old Town Key West. Looking north, you’re less than two blocks from downtown old town – looking south you’re less than two blocks from the Truman Waterfront Park and Fort Zachary Taylor State Park and Beach. 


old town caribbean estate
New
special rates available

10BR 7.5 BA

June 16 - June 22
June 29 - July 2
July 27 - Aug 3
Nightly $2400
Weekly $11500


Standard Rates: $11800 - $25220 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.


island interlude
special rates available

2BR 2.5BA


June 14 - July 31

Monthly $5350


Standard Rates: $4800 - $9825 per month

2BR 2.5BA - Sleeps 4
Upscale Town home in gated bricked pool-garden courtyard
Shared Dipping pool with waterfall
Around the corner from trendy Petronia Street where you find Blue Heaven
Short Street from entrance to Fort Zachary Taylor Beach

Aspirational, luxurious, well appointed, and whimsical, are four attributes that make this courtyard townhome a lovely place to call home in Key West. Aptly named, Island Interlude, this 2-story property is situated around the corner from one of the most popular transitional urban scenes of Key West. 


on hemingways rounds
New
special rates available

2 BR 2 BA

Aug 1- Aug 31

Monthly $5900


Standard Rates: $6500 - $14650 per month

2BR 2BA - Sleeps 4
Beautifully Renovated 1920 Bungalow
Private Swimming Pool & Sun Deck
Upscale Amenities
On Famous Whitehead St.
1 Block off Duval Street

On Hemingway's Rounds, is an inspired renovation of a classic circa 1920 American Bungalow redone Key West style. Private swimming pool garden and deck in the fenced back yard. Historic front porch with comfy chairs to relax and watch Key west go by. Interior design is imaginative and elegant. Less than one block from the Hemingway Home and Museum. 

 


havana moon over duval
special rates available

2BR 2BA

June 30 - July 15
Nightly $550
Weekly $2600


Standard Rates: $2475 - $5820 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.

 


island elegance
special rates available

3BR 3BA

Sept 1- Sept 30

Monthly $5950


Standard Rates: $6350 - $13800 per month

3BR 3BA - Sleeps 6
NEW Swimming Pool Garden with Spacious Deck installed Fall 2021
Timeless Historic Features
Split-bedroom Design
Tropical Landscaping
Bricked Private Driveway
Close to Key West Beaches on the South Shore

Channeling the island spirit in oft-missed mid-town, this pool-garden home makes an enviable Key West hideaway. Timeless craftsman-colonial architecture. New swimming pool with spacious sun deck. Lush mature tropical landscaping.

Here you live removed from the hubbub, yet close enough to beaches and Old Town. With a luxuious outdoor poolside living room, you may even find yourself making new island rituals of reading, and sipping Cuban coffee or your favorite cocktail on the deck.


villa deja vu key west
special rates available

4BR 3BA

June 13 - June 22
June 28 - July 2
July 15 - July 31
Nightly $975
Weekly $5300


Standard Rates: $5250 - $11075 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.


private pool garden villa
special rates available

3BR 2.5BA

June 13- June 17
June 27 - July 6
July 21 - July 27
Nightly $725
Weekly $3900


Standard Rates: $720 - $6950 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.


classic key west estate
special rates available

7BR 5.5BA

June 16 - June 22
June 29 - July 2
July 27 - Aug 3
Nightly $1900
Weekly $10400


Standard Rates: $1080 - $19050 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. 


key west wabi sabi
special rates available

4BR 3.5BA

June 17 - July 11
July 16 - July 23

Nightly $875
Five nights $3950
Weekly $4400


Standard Rates: $4650 - $9950 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.


island cosmopolitan cottage
special rates available

3 BR 2 BA

July 1- July 31

Monthly $6900


Standard Rates: $6900 - $15200 per month

3 BR 2 BA
Sleeps 4 - 6
Historic Cottage
Upscale Renovation and Interior Design
Large Lap-Swimming Pool
Quiet Neighborhood close to White St.
Easy walk to Higgs Beach

An upscale renovation with elegant furnishings, this heritage cottage has all the luxuries you could want and still enjoy the ambiance of staying in an historic Key West property. Mixing a dash of contemporary style with selected cottage pieces, the designer created a unique island style cosmopolitan hide-away in the White Street Gallery district of Old Town Key West. 


the caroline house
special rates available

5BR 3BA

June 8- June 13
June 27 - July 6

Nightly $1250
Weekly $6500


Standard Rates: $6645 - $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

June 13 - June 30
July 7 - July 14
Nightly $875
Weekly $4500


Standard Rates: $4650 - $9950 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

June 15 - June 21
June 24 - July10

Nightly $975
Weekly $5300


Standard Rates: $5250 - $11075 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

June 12 - June 15
July 8 - July 18
Nightly $550


Standard Rates: $2445 - $5650 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. 

 


tropical tranquility
special rates available

4BR 4BA

June 30 - July 6

Nightly $1050
6 Nights $5800


Standard Rates: $5420 - $12570 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.

 


key west island village cottage
special rates available

1 1/2 BR 1BA

Monthly

July 8 - Aug 31
Monthly $4975


Standard Rates: $4750 - $11300 per month

2BR 1.5 BA - Sleeps 2-6
Award Winning Historic Cottage
Private Dipping Pool in Tropical Garden
Great For Small Family
Historic Seaport Neighborhood
5 Minute Walk to Seaport Docks

Story-book charm, originally built in 1860, a restoration won it the coveted Star Award by the Historic Florida Keys Foundation, in 1995. Situated on famous Southard St., in the Historic Seaport neighborhood, its unique character has so captured lovers of Key West homes and gardens, that it’s been featured in two books - Mary Emmerling’s American Country Cottages, 1993, and again in Key West Gardens and Their Stories, Frawley-Holler, 2000.


pavilion villa
special rates available

4BR 3BA

June 16 - June 19
July 6 - July 18

Nightly $925
Weekly $4900



Standard Rates: $5250 - $11075 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

June 24 - June 29
July 8 - July 14
July 19 - July 25
Nightly $475


Standard Rates: $2390 - $5550 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

June 21 - June 29
July 6- July 18
Nightly $625
Weekly $3325


Standard Rates: $2580 - $6250 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.

 


twice as nice on duval street
special rates available

4BR 4BA

June 30 - July 15
Nightly $925


Standard Rates: $5245 - $10500 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.

 


key west dreamin
special rates available

2BR 2BA

June 17 - June 20
July 4 - July 7
July 12- July 18

Nightly $650
Weekly $3100


Standard Rates: $3035 - $7170 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.

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