Key West Time
August 22nd
2:47am · 82°F
August 22nd
2:47am · 82°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.
** Trip Insurance Special: Promotional credit is currently available for purchasing trip insurance for stays between Aug 10 and Oct 20.
2-3 Bedroom - $25 credit per night
4-5 Bedroom - $50 credit per night
6-7 Bedroom - $75 credit per night
11 Bedroom - $125 credit per night
There are no special deals at this time.
Aug 26- Aug 29
Nightly $775
Sept 2- Sept 21
Weekly $4250
Standard Rates: $3950 - $8325 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.
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.
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!
Aug 22 - Oct 14
Weekly $1300
Standard Rates: $1400 - $2550 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.
Aug 22- Aug 30
Weekly $1875
Nightly $350
Sept 15- Sept 30
Weekly $1875
Standard Rates: $1700 - $3325 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.'
Aug 22- Aug 29
Sept 5- Sept 26
Weekly $3500
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.
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.
Aug 22- Aug 31
Weekly $1650
Sept 1- Sept 30
Weekly $1550
Mar 7- Apr 4/2020
4 weeks $7350
Standard Rates: $1500 - $2950 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.
Aug 22 Sept 30
Monthly $4800
Standard Rates: $5400 - $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.
Aug 24- Aug 30
6 nights $1800
nightly $400
Sept 7- Sept 14
Sept 20- Oct 2
Weekly $1975
Standard Rates: $1800 - $4025 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.
Aug 22- Aug 29
Sept 14- Sept 19
Sept 23- Sept 26
Weekly $3975
Nightly $750
Standard Rates: $3750 - $7600 per week
4BR 3.5BA - Sleeps 10
(4BR, 4BA, effective Nov 1)
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."
Aug 22- Aug 31
Weekly $2100
Sept 1- Sept 16
Weekly $1950
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.
Sept 10- Sept 25
Weekly $1775
Fantasy Fest
Weekly $2900
Standard Rates: $1925 - $3625 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.
Aug 24- Aug 30
Sept 7- Sept 17
Weekly $3500
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.
Fantasy Fest
Weekly $5300
Standard Rates: $2600 - $6300 per week
3BR 2.5BA - Sleeps up to 5
Stroll to the Beach
Truman Annex residence with Ocean View from Bedroom Balconies
Short Walk to all Downtown Old Town Key West Features
Rent this Key West Luxury Home and Experience a Remarkable Piece of American Architectural History. A renovated 'Truman Treasure', in one of the most desirable Ocean Front Old Town Key West locations.
Aug 22- Sept 14
Weekly $3975
Nightly $700
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.
Aug 22 - Aug 29
Weekly $2300
Nightly $450
Sept 2- Sept 6
Sept 9- Sept 25
Weekly $2100
Nightly $450
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.
Aug 25- Sept 8
weekly $1750
Standard Rates: $1900 - $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.’
Aug 25- Sept 6
Sept 9- Sept 20
Weekly $6225
Nightly $1500
Standard Rates: $6375 - $12500 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.
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.
Aug 22- Aug 29
Sept 2- Sept 24
Weekly $7550
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.
Aug 16 - Aug 21
Nightly $400
Aug 25- Sept 4
Weekly $1950
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."
Sept 2- Sept 14
Weekly $4550
Standard Rates: $3900 - $8675 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.
Aug 22- Aug 29
Sept 5- Sept 26
Weekly $1750
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.
Aug 22- Aug 31
Weekly $1950
Sept 15- Sept 26
Weekly $1950
Fantasy Fest
Weekly $3200
4 nights $2400
Standard Rates: $1900 - $4000 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.
Aug 26- Aug 29
Weekly $3975
Sept 21- Sept 25
Nightly $700
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.
Aug 26- Aug 31
Sept 9- Sept 21
Weekly $2100
Nightly $450
Standard Rates: $1800 - $4025 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 ...
Aug 22- Aug 29
Sept 5- Sept 26
Weekly $1750
Nightly $375
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.
Aug 22- Aug 30
Weekly $3975
Sept 15- Sept 26
Weekly $3975
Standard Rates: $3750 - $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.
Aug 22- Aug 29
Sept 2- Sept 18
Sept 22- Sept 30
Weekly $1975
Standard Rates: $1850 - $3845 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.
Standard Rates: $1675 - $2975 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.
Standard Rates: $2050 - $3550 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.
Aug 22- Sept 30
Weekly $1750
Fantasy Fest
Weekly $2900
Standard Rates: $1900 - $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.
Aug 25 - Aug 30
Nightly $975
Sept 11- Sept 28
Weekly $4950
Standard Rates: $4500 - $9500 per week
5BR 3BA Classic Victorian House - Sleeps 10
Plus 2BR 1/2 story Caribbean Bungalow
Heated Pool
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.
Aug 23- Aug 29
Six nights $3650
Sept 2- Sept 15
Weekly $4150
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.
Aug 25- Aug 29
Nightly $400
Sept 2- Sept 30
Weekly $1975
Fantasy Fest
weekly $3100
4 nights $2400
Standard Rates: $1750 - $3845 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."
Aug 22- Aug 31
Weekly $2700
Sept 1- Sept 13
Sept21- Oct 9
Weekly $2450
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.
Aug 25- Aug 29
Nightly $650
Sept 2- Sept 5
Sept 8- Sept 17
Weekly $3500
Nightly $700
Standard Rates: $3600 - $6700 per week
Large Private Swimming Pool
with Spacious Outdoor Cabana
4BR 3.5BA Main house plus Studio Cottage
Sleeps 8
During the months of May through January 2, this genuine Key West combo of our Private Pool Garden Villa plus a classy private studio cottage that adjoins the property can be your very own get-away.
