Key West Time
December 8th
11:07am · 78°F
December 8th
11:07am · 78°F
* 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.
Apr 1- Apr 30
$4100
Standard Rates: $3400 - $6025 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.
Nov 30- Dec 4
Nightly $400
Dec 8- Dec 21
weekly $1900
Standard Rates: $400 - $4000 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!
January 2- January 31
$5900
Standard Rates: $3500 - $7700 per month
3BR 1 BA Sleeps 4
Historic Seaport Location
Expansive Porch overlooks Pool
Exclusive Use of Pool
A delightfully renovated three-bedroom one-bathroom hideaway, with swimming pool, that encompasses the entire 2nd floor of a historic Key West wooden house. From this location you’re only four streets from the famous wharf where the old schooners, charter boats, and luxury yachts dock. A testimony to its vintage, this charming 19th century seaport building displays an intriguing sawtooth roof - a succession of three gable roofs with valleys in between - which accentuates the historic relevance of the house.
Mar 21- Mar 28
Weekly $1975
Standard Rates: $1350 - $2650 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.
Nov 20- Nov 24
Weekly $4250
Nightly $775
Dec 16- Dec 21
Nightly $700
Jan 8- Jan 11
Nightly $800
Feb 2- Feb 8
Weekly $6475
Feb 29- Mar 7
Weekly $6475
Standard Rates: $4100 - $8525 per week
5-6BR (Sleeping Porch) - Sleeps 12+
Attached 1BR Cottage
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.
Nov 30 - Dec 4
Nightly $650
Dec 8- Dec 21
Weekly $3500
Nightly $700
Jan 4- Jan 10
Nightly $775
6 nights $3750
Jan 20- Jan 25
Nightly $900
5 nights $3700
Standard Rates: $3600 - $7125 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.
Nov 30- Dec 7
Dec 14- Dec 18
Weekly $3500
Nightly $675
Jan 11- Jan 15
Nightly $700
Standard Rates: $3000 - $6300 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.
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.
Dec 12- Dec 21
Weekly $1550
8/9 Nights $1700
Standard Rates: $1500 - $3100 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.
Jan 4- Jan 10
Six Nights $2100
Jan 22- Jan 25
Nightly $400
Standard Rates: $1850 - $4125 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.
Dec 13- Dec 20
Weekly $6225
Nightly $1300
Jan 4- Jan 8
Jan 13- Jan 16
Nightly $1500
Feb 2- Feb 8
Six nights $8600
Standard Rates: $6375 - $12800 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.
Nov 23- Nov 26
Weekly $1875
Nightly $375
Standard Rates: $1700 - $3425 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.'
Apr 1- Apr 30
Monthly $4900
Standard Rates: $4700 - $9500 per month
3BR 3BA - Sleeps 6
Timeless Historic Features
Split-bedroom Design
Spacious Front Porch
Tropical Landscaping
Bricked Private Driveway
Close to Key West Beaches on the South Shore
Channeling the island spirit in oft-missed mid-town, this home makes a classical curbside statement. Timeless craftsman-colonial architecture, lush mature tropical landscaping.Here you live away from the hubbub, yet close enough to beaches and Old Town. With many places to place a hammock, you may even find yourself making a new daily island ritual of swinging, reading, and sipping wine.
Nov 21- Nov 24
Dec 1-Dec 4
Dec 9- Dec 21
Weekly $7050
Nightly $1500
Jan 4- Jan 8
Jan 12- Jan 17
Nightly $1800
Jan 21- Jan 28
Weekly $9400
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.
Nov 20- Nov 24
Dec 1- Dec 5
Weekly $3975
Nightly $750
Jan 4- Jan 7
Nightly $800
Feb 3- Feb 8
Five nights $4425
Standard Rates: $3750 - $7800 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."
Dec 28- Jan 3
Six nights $8000
Feb 2- Feb 10
7 or 8 nights available
Standard Rates: $4650 - $9700 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.
Nov 14- Nov 18
Nov 24- Nov 27
Dec 9- Dec 12
Weekly $3500
Nightly $675
Jan 11- Jan 18
Jan 25- Feb 1
Weekly $3900
Mar 7- Mar 14
Weekly $4950
Standard Rates: $3600 - $7125 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.
Nov 28- Dec 4
Weekly $1900
Nightly $400
Jan 12- Jan 16
Nightly $400
Mar 21- Mar 28
Weekly $3100
Standard Rates: $1850 - $4025 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.
Dec 1- Dec 12
7/8 nights $1500
Standard Rates: $1800 - $3725 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.
Jan 9- Jan 19
Weekly $2700
10 Nights $3350
Standard Rates: $1750 - $3950 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.’
Nov 18- Nov 22
Nov 30- Dec 5
Dec 9- Dec 12
Nightly $700
Weekly $3975
Jan 20- Jan 25
Nightly $900
5 nights $3900
Jan 25- Feb 1
Mar 21- Mar 28
Weekly $5600
Mar11-Mar 15
Nightly $850
Standard Rates: $3750 - $7800 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.
Nov 20- Nov 26
Weekly $3850
Nightly $875
Jan 5- Jan 8
Jan 12- Jan 17
Jan 21- Jan 25
Nightly $850
Feb 29- Mar 7
Weekly $5600
Standard Rates: $3750 - $7800 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.
Nov 30- Dec 5
Nightly $425
Weekly $1900
Jan 23- Jan 25
2 Nights $725
Standard Rates: $1950 - $4400 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.
Nov 30- Dec 7
Dec 14- Dec 21
Weekly $1750
Nightly $375
Jan 11- Jan 15
Nightly $400
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.
Nov 20- Nov 23
Nightly $1000
Standard Rates: $3900 - $8875 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.
Dec 14- Dec 20
5/6 Nights $1600
Nightly $400
Jan 19- Jan 25
Six nights $2200
Jan 25- Feb 1
Weekly $2600
Standard Rates: $1800 - $3950 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."
Dec 17- Dec 21
Weekly $2100
Nightly $450
Standard Rates: $1850 - $4125 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 ...
Feb 29- Mar 6
Six Nights
$3650
Standard Rates: $3300 - $5300 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.
Jan 4- Jan 9
Nightly $900
5 nights $3600
Standard Rates: $3750 - $7800 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.
Nov 30- Dec 7
Dec 14- Dec 18
Weekly $1750
Nightly $375
Jan 11- Jan 15
Nightly $400
Standard Rates: $1550 - $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.
Nov 23- Nov 26
Nightly $400
Standard Rates: $1900 - $4100 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.
Nov 23- Nov 26
Weekly $3975
Nightly $750
Standard Rates: $3750 - $7500 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.
Nov 20- Nov 23
Dec 8- Dec 12
Dec 16- Dec 21
Weekly $1950
Nightly $400
Jan 4- Jan 6
Feb 18- Feb 22
Nightly $525
Standard Rates: $1850 - $3945 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.
Nov 11- Nov 24
Weekly $1700
also available to book now
Jan 8- Jan 11
Nightly $400
Jan 18- Jan 26
Weekly $2350
Standard Rates: $1750 - $3075 per week
2BR 1BA - Sleeps 4-6
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.
Dec 16- Dec 21
Weekly $1900
Nightly $400
Jan 8- Jan 11
Nightly $425
Standard Rates: $2050 - $3650 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.
Nov 20 - Dec 21
Weekly $1750
Jan 8- Jan 18
Weekly $2900
10 Nights $3500
Standard Rates: $1750 - $3950 per week
2BR 2.5BA - Sleeps 4
Contemporary Interior Design Built in Historic Brick Architecture
Shared Pool in Gated Garden
Short Walk to Fort Zachary Beach
Close to Key West Water Park
Stroll to Downtown Old Town
A striking tri-level condominium situated in Key West's most historic gated Truman Annex waterfront luxury neighborhood, offers a beautiful combination of classic historic charm and refined modern ambience. Perfect location to enjoy the Truman Waterfron Park Ampitheater.
Nov 20- Dec 4
Dec 8- Dec 12
Dec 16- Dec 21
Weekly $1950
Nightly $400
Jan 4- Jan 9
Nightly $450
Jan 13- Jan 26
nightly $500
Weekly $2300
Feb 2- Feb 8
six nights $2800
Standard Rates: $1850 - $3945 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."
January 2-January 31
$7900
Standard Rates: $4600 - $9600 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.
Nov 18- Nov 24
Six nights $3900
Nightly $800
Dec 1- Dec 5
Dec 17- Dec 21
Nightly $800
Jan 11- Jan 17
Six Nights $4300
Feb 2- Feb 8
Six Nights $5300
Mar 14- Mar 21
Weekly $5650
Standard Rates: $3750 - $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.
May 8- May 15
Weekly $2950
Standard Rates: $2300 - $5025 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.
