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August 13th
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Key West ~ Duval Street Vacation Rentals

Key West vacation rentals on Duval street offer a unique opportunity to stay on Duval Street or within a few minutes' walk away. Duval Street Key West is a world-famous roadway that spans from the Atlantic Ocean to the Gulf of Mexico, in only 1.25 miles! With Key West South Beach at one end, Mallory Square at the other, and acclaimed restaurants, iconic bars, boutique shopping, museums, historic churches, and live entertainment in between - it's all here nearly right out your door.

Choose from our special inventory of Duval Street Vacation rentals, including cottages, villas, penthouses, flats, even a fine luxury estate. Either Key West vacation rentals on Duval Street, or properties just around the corner, are an excellent choice for travelers looking to spend their time near the most famous area of Key West.

* PLEASE NOTE: Some properties displayed may not be available for rent due to other inquiries and pending reservations. Please contact our office to be sure of availability. info@vhkw.com or 305-294-7358 ext. 1


vintage luxury cottage on duval
special rates available

1BR 1BA

Aug 17 _ Aug 24
Aug 28 - Sept 17
Sept 11- Sept 17
Sept 24- Sept 30
Nightly $450
Weekly $2275

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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.  


island rendezvous

Standard Rates: $6455 - $15850 per week

6BR 5BA - Sleeps 14
2 heated swimming pools
3 Cottage Compound (2-cottage villa plus a cottage).
Less than 1/2 block off Duval Street

Get together for an 'Island Rendezvous' in Key West in this Award Winning Villa and Caribbean Style Cottage side-by-side steps from Duval St. and 3.5 Blocks from Mallory Square. Perfect solution for a gathering of family or friends for a week in paradise.


the grand marshall
New

Standard Rates: $11700 - $32800 per month

5BR 4.5 BA - Sleeps 10
2 Heated Swimming Pools
2 Upscale Renovated Houses w/ Fenced Backyards that border each other.
1/2 Block from the Hemingway House & Museum
1 block off Duval Street

If you plan to stay with your family or friends, but treasure your own place to retreat,The Grand Marshall offers the perfect layout. A back-to-back combination of 2 upscale renovated and beautifully decorated historic homes. Around the corner from the Hemingway Home and Museum, one block off Duval St. Settle in for a month or more and become thoroughly relaxed and ‘islandized.’


governors retreat

Standard Rates: $6500 - $19000 per month

3BR 2.5BA - Sleeps 6
Upscale renovation of Historic Home on Picturesque Lane
Private Swimming Pool w/ Sun Deck
1st & 2nd FL Covered Porches
Expansive Porch Room off Master BR
Off-Street Parking
1 Block Off Duval

Governor's Retreat is situated on a less-traveled lane that exudes sought after charm and character. Pictorial 1900’s historic home with upscale renovations and amenities. Exquisite and imaginative décor. Private pool and deck in fenced tropical garden. Multiple sitting porches in the front and back of the house. A block from the Hemingway Home and Museum.  

 


cockadoodle cottage on duval
special rates available

2BR 2BA


Aug 9 - Sept 30
Nightly $475
Weekly $1900




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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.'

 


on hemingways rounds
New

Standard Rates: $5200 - $13800 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. 

 


villa deja vu key west
special rates available

4BR 3BA

Aug 28 - Sept 8
Sept 12 - Sept 24

Nightly $975
Weekly $4850

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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.


havana moon over duval
special rates available

2BR 2BA

Aug 14 - Aug 19
Aug 23 - Sept 3
Sept 12- Sept 16
Sept 20 - Sept 30
Weekly $2600
Nightly $525

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Standard Rates: $2190 - $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.

 


caribbean cottage ~ duval street key west
special rates available

2BR 2BA

Aug 17 - Aug 21
Sept 6 - Sept 9
Sept 16- Sept 30
Nightly $550
Weekly $2600

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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

Aug 14 - Aug 26
Aug 31 - Sept 30

Weekly $4650
Nightly $825

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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.


heavenly hideout at rainbows end
special rates available

4BR 4BA

Aug 12- Sept 30
Weekly $4650
Nightly $825

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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.

 


amelias hideaway
special rates available

4BR 4BA

Aug 8 - Aug 13
Aug 20 Aug 25
Aug 28 - Sept 2
Sept 6 - Sept 12
Sept 18- Sept 23
Weekly $5200
Nightly $975

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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

Aug 14 - Aug 18
Aug 22 - Sept 12
Sept 25 - Sept 30

Nightly $550
Weekly $2650

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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.

 


pavilion villa
special rates available

4BR 4BA

Aug 9 - Aug 13
Aug 22 - Aug 25
Aug 29 _ Sept 7
Sept 14 - Sept 22
Sept 25 - Sept 30
Nightly $975
Weekly $5200

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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. 


duval street fantasy resort villa

Standard Rates: $4350 - $10100 per week

3BR 3BA - Sleeps 8
Just Off Upper Duval Street
Private Adjoining Cottages
with 2 Private Pools

Rare one-of-a-kind property, on Duval Street, yet hidden from the street. Two cottages jointed with a bricked courtyard and swimming pool create a secret resort residence. 


twice as nice on duval street
special rates available

4BR 4BA

Aug 14 - Aug 19
Aug 23 - Sept 3
Sept 20 - Sept 30

Nightly $975
Weekly $5200

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Standard Rates: $4400 - $9705 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

Aug 14 - Aug 20
Aug 27 - Sept 9

Weekly $2975
Nightly $650

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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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