Key West Duval Street Vacation Rentals
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  • (305) 294-7358
info@vhkw.com
Key West Time
March 22nd
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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
special rates available

June 15- June 22
weekly $2200

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Standard Rates: $1800 - $3850 per week

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

Vintage Luxury Cottage - An elegant Cottage with Private Heated Pool in hidden courtyard. "Best Kept  Key West Secret."


island rendezvous

Standard Rates: $5600 - $11925 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.


heavenly hideout at rainbows end
special rates available

March 30- Apr 6
April 6- April 13
April 13-April 20
weekly $3900
Nightly $775

May 27- June 1
June 8- June 13
Nightly $750

June 17- July 25
Weekly $3975

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Standard Rates: $3500 - $6925 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.

 


the meeting point   key west

Standard Rates: $10500 - $20820 per week

11BR 11BA - Sleeps up to 22
2 heated swimming pools (1 with Spa Jets)
Steps from the 500 block of Duval Street
3-story historic Victorian home plus new 4 BR villa

"Let's stay together ... for a week or more." Start calling your family and make a plan. If you’re looking for luxury and plenty of room, The Meeting Point Key West is the grandest vacation rental licensed to rent weekly in Key West, both in stature and style. 7 BR 7 Full BA elegant Victorian Mansion plus 4 BR 4 Full BA luxury villa. 


cockadoodle cottage
special rates available

Apr 6- Apr 13
weekly $2250

June 10- July 20
Weekly $2025

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Standard Rates: $1700 - $3325 per week

2BR 2BA
Sleeps 4 - 6
Great for 2 Couples or Small Family
Jacuzzi Bath Tub
Charming Upper Duval St. Neighborhood
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.'

 


penthouse on duval
special rates available

Apr 20-Apr 25
Nightly $700

May 28- June 4
Nightly $675

June 15- June 23
Weekly $1900



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Standard Rates: $3000 - $6200 per week

4BR 4BA + (2 1/2 BA) - Sleeps 8
2 Kitchens
Entire 2nd + 3rd floors of the building
Porch overlooks Duval Street in the 700 Block.
Spacious deck in the back.
Adult Location

Perfectly staged on Duval Street Key West, this unique downtown Key West rental received a major renovation to become the  fabulous "Penthouse On Duval." Stroll to South Beach and Mallory Square. Plenty of room to spread out. Enviable Fantasy Fest location!  Mallory Square and the beach.


amelias hideaway
special rates available

May 12- May 15
Nightly $750

May 19- May 26
June 17- June 28
July 7- July 20
Weekly $4575

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Standard Rates: $3600 - $7600 per week

4BR 3.5BA - 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

Mar 30 Apr 5
six nights
$2600
Nightly $475

May 18- May 26
June 2- July 15
Weekly $2350

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Standard Rates: $1850 - $3925 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

April 20- April 26
Six nights $3500
Nightly $775

May 10= May 13
Nightly $700

May 27- June 3
June 16- June 29
July 6- July 20
Weekly $3975

Dec 24- Dec 28
4 nights $3500

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Standard Rates: $3500 - $6925 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. 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.


down island digs
special rates available

Apr 6- Apr 13
Weekly $2850

May 17- June 1
Weekly $2500

June 26- June 29
Nightly $400

Oct 25 - Oct 28
Fantasy Fest
$1950

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Standard Rates: $1950 - $4300 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.

 


villa deja vu key west
special rates available

Mar 30 - Apr 4
5 nights $4100
Nightly $875

April 12- April 24
weekly $5100
Nightly $875

May 11- May 18
weekly $4575

June 6- June 12
Six nights $3900

June 23- July 13
Weekly $4575

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Standard Rates: $3750 - $7600 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

Mar 31- Apr 4
Nightly $1750

Apr 7- Apr 13
Nightly $1750
Six nights $8750

May 12- May 19
Weekly $8250

June 2- June 5
Nightly $1500

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Standard Rates: $6900 - $13345 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.


key west spa villa
special rates available

Mar 30- Apr 6
Apr 13- Apr 20
Weekly $5250

April 20- April 27
Weekly $4700

May 270 June 2
Six nights $3900

June 9- June 13
Nightly $700

June 19- June 29
Weekly 44575

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Standard Rates: $3600 - $7600 per week

4BR 4BA - Sleeps 8
Dipping Pool w/ Waterfall
Large Hot Tub
Sun Deck
Just off Upper Duval Street

This proud 1890's 'cigar maker's cottage, just off Duval Street, has been lovingly transformed into a stylish 4 bedroom, 4 bathroom spa villa. Captivated by the uninhibited yet wonderfully elegant Key West island life-style, the designer created a fabulous balance of opposites.


havana moon
special rates available

Mar 30- Apr 6
weekly $2800
Nightly $500

Apr 20 Apr 26
Nightly $450

May 11- May 18
June 15- June 30
Weekly $2250

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Standard Rates: $1900 - $4075 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.

 


city island view
special rates available

Apr 9- Apr 13
Apr 20-Apr 25
Nightly $400
5 nights $1800

May 28- June 4
Nightly $375

June 15- June 23
weekly $1900

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Standard Rates: $1550 - $3650 per week

2BR 2.5BA - Sleeps 4
Best for Adults
Great view of Duval St. below in the 700 block.

Perched just above the fun and frolic of Duval Street you're sure to capture the "island beat" that stirs this tiny tropical island of Key West, Florida. Easy stroll to Mallory Square and South Beach.


pavilion villa
special rates available

Apr 29- May 2
May 29- June 1
May 6- May 9
May 12- May 16
Nightly $625

July 1- July 6
Five nights $3425

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Standard Rates: $3600 - $7600 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.


starlight siesta
special rates available

Mar 27- Mar 30
Apr 9- Apr 13
Apr 20-Apr 25
Nightly $400

May 28- June 4
Nightly $375

June 15- June 23
weekly $1900

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Standard Rates: $1500 - $3650 per week

2BR 2.5BA - Sleeps 4
Private back deck at end of lane off Duval St. in the 700 block. Island urban. Best for Adults.

Cleverly staged in the island's city center, this downtown Key West rental is located in the 700 block of Duval Street, at the end of a narrow urban 'dead end' lane. Completely hidden from view on the 2nd and 3rd levels, spacious and creative renovation. Easy stroll to Mallory Square and South Beach.


fantasy resort villa

Standard Rates: $3600 - $7600 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
special rates available

June 15- June 30
Weekly $4275

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Standard Rates: $3600 - $7300 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.

 


on hemingways rounds

Standard Rates: $4500 - $9300 per month

3BR 2BA - Sleeps 6
Private Spa Garden with Pool & Waterfall
1/2 block off Duval St.

On Hemingway's Rounds, is an inspired renovation of a classic 1930's ‘American Bungalow’ redone Key West style.  While the street side remains true to the original casual arts-and-crafts form, the interior now boasts an elegant simplicity that meets even the most discerning of modern tastes.

 


villa nouveau key west
special rates available

Mar 30- Apr 6
Weekly $4900
Apr 29- May 2
May 7- May 11
May 18- May 23
June 2- June 8
Nightly $800

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Standard Rates: $3600 - $7600 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.

 


key west dreamin
special rates available

May 30- June 5
Six nights $2550

June 23- July 20
Weekly $2950

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Standard Rates: $2300 - $4925 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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