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COVID-19 INFO
Key West Time
May 20th
2:46am · 79°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.


dancing palms villa
special rates available

2BR 2Ba

June 18- June 25
Weekly $3150


Standard Rates: $2300 - $5145 per week

2BR 2BA - Sleeps 4
Manicured Tropical Swimming Pool Garden
Shared Heated Pool
Walk to Duval St. in 3 minutes

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.


elegant key west tree house
special rates available

2BR 1BA

May 15- June 30

Monthly $4200


Standard Rates: $3750 - $7350 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.


seaport hideaway
New
special rates available

2BR 1.5BA

June 1- June 30

Monthly $4500


Standard Rates: $4750 - $8850 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.

 


hidden story book cottage
special rates available

1BR 1BA

May 15 - June 30

Monthly $3750


Standard Rates: $3200 - $5700 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.

 


old town caribbean estate
New
special rates available

10BR 7.5 BA

May 21 - May 26
May 31 - June 8
Weekly $9800
Nightly $1700


Standard Rates: $10080 - $22200 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.


key west poolside loft
New
special rates available

2BR 2BA

May 15 - June 30

Monthly $4150


Standard Rates: $4500 - $8400 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.


cockadoodle cottage on duval
special rates available

2BR 2BA

May 31- June 11

Nightly $475
Weekly $2550



Standard Rates: $1895 - $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.'

 


butterfly garden
special rates available

1BR !BA

May 15- June 30

Monthly $3800


Standard Rates: $3300 - $5750 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

May 20 - May 29
June 2 - June 15
Weekly $2900
Nightly $575


Standard Rates: $2115 - $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.


exclusive key west beach front
special rates available

2BR 3BA

June 4 - June 11
June 18 - June 25
Weekly $2800


Standard Rates: $2030 - $5355 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 !BA

June 2 - June 18
Weekly $1800


Standard Rates: $1485 - $3390 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. 


island elegance
special rates available

3BR 3BA

May 15- June 30

Monthly $6250


Standard Rates: $5000 - $12800 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.


flower power house
special rates available

6BR 4BA

May 15- May 20
June 19 - June 25

Weekly $5900
Nightly $975


Standard Rates: $4750 - $11065 per week

6BR 4BA- 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.


villa deja vu key west
special rates available

4BR 3BA


May 25- May 28

Nightly $975


Standard Rates: $4345 - $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.


island interlude
special rates available

2BR 2.5BA

June 13- July 19
Monthly $4975


Standard Rates: $3950 - $8950 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. 


private pool garden villa
special rates available

3BR 2.5BA


May 14- May 21
June 22- July 16
Weekly $4100
Nightly $750


Standard Rates: $3710 - $6915 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.


island brownstone
special rates available

2BR 2BA

May 22- June 4
June 11- June 20

Weekly $2475


Standard Rates: $1760 - $5255 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.’


caribbean cottage ~ duval street key west
special rates available

2BR 2BA


June 4- June 8
June 12- June 22
Nightly $550
Weekly $3100


Standard Rates: $2190 - $5220 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. 

 


key west wabi sabi
special rates available

4BR 3.5BA

June 18 - June 30

Weekly $4975


Standard Rates: $4195 - $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.


classic key west estate
special rates available

7BR 5.5BA

May 21- May 26
May 31 - June 7
Weekly $7500
Nightly $1500


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. 


tree tops
special rates available

2BR 2BA

May 15- May 20
June 11- June 25
Nightly $450
Weekly $2500


Standard Rates: $2060 - $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.


heavenly hideout at rainbows end
special rates available

4BR 4BA

June 4- June 30

Weekly $4975


Standard Rates: $4195 - $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.

 


vintage luxury cottage on duval
special rates available

1BR 1BA

May 24- May 27
June 3 - June 8
Nightly $450


Standard Rates: $1970 - $5120 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.  


little red pool garden cottage
special rates available

2BR 2BA

May 15 - June 30

Monthly $4800


Standard Rates: $3850 - $12100 per month

2 BR 1 BA
Sleeps 2 - 4
Private Pool
Idyllic Pool-Garden Island Cottage
Close to the Beach
Quiet Neighborhood on lane less traveled

‘Heads Up’ to all of you incurable romantics who are looking for the perfect Old Town Key West garden cottage retreat close to the beach. Dream worthy and authentic, it’s a little bit like ‘Little Red Riding Hood’s cottage merges with a ‘Fantasy Island’s’ private pool garden,’ and the two are seamlessly blended.


garden suite
special rates available

3BR 2BA

May 15- May 20
June 19 - June 25
Weekly $2800
Nightly $525


Standard Rates: $2375 - $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.


amelias hideaway
special rates available

4BR 4BA

June 11 - June 25
Weekly $5875


Standard Rates: $4345 - $10100 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."

 


down island digs
special rates available

2BR 2BA


May 16 - May 20
May 27 -June 1
June 9 - June 26
Nightly $550
Weekly $3100


Standard Rates: $2230 - $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.

 


tropical tranquility
special rates available

4BR 4BA

May 29 - June 2
June 13- June 19

Nightly $1075


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.

 


a tropical tradition
special rates available

3BR 2.5BA

May 22 -May 25
May 29- June 1

Nightly $575


Standard Rates: $2265 - $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.


the caroline house
special rates available

5BR 3BA

May 28 - June 4

Weekly $6875
Nightly $1275


Standard Rates: $5345 - $12625 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.


pavilion villa
special rates available

4BR 4BA

May 22 - May 26
May 30 - June 4
June 8 - June 11
Nightly $950


Standard Rates: $4345 - $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. 


cocos poolside retreat
special rates available

3BR 2.5BA

May 22- May 25
May 29 - June 2
June 11- June 15

Weekly $2800
Nightly $600


Standard Rates: $2265 - $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."


key west dreamin
special rates available

2BR 2BA

May 31- June 5
June 17 - June 26
Weekly $3500
Nightly $650


Standard Rates: $2600 - $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.

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