Key West Time
October 6th
9:08am · 82°F
October 6th
9:08am · 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.
There are no special deals at this time.
2BR 2Ba
Oct 15- Oct 22
Weekly $3150
Oct 22- Oct 29
Weekly $3500
Standard Rates: $2535 - $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.
2BR 1BA
Oct 5- Nov 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.
1BR 1BA
Oct 25 - Nov 30
Rental $3900
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.
10BR 7.5 BA
Dec 23 - Dec 26
$9900
Jan 2 - Jan 12
Weekly $13500
Jan 16- Jan 19
Nightly $2750
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.
2BR 2BA
Oct 5- Oct 14
Oct 17 - Oct 23
Nightly $475
Weekly $1900
Oct 22- Oct 30
Weekly $2875
Nightly $650
Standard Rates: $1895 - $4420 per week
2BR 2BA
Sleeps 4
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.'
2BR 2BA
Oct 5- Oct 13
Oct 16 - Oct 20
Weekly $2700
Nightly $550
Standard Rates: $2230 - $5315 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!
1BR !BA
Monthly $3600
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.
3BR 2BA
Oct 12 - Oct 15
Weekly $2500
Nightly $550
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.
2BR 3BA
Sept 5 - Oct 15
Weekly $2100
Standard Rates: $2115 - $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 ...
2BR 1BA
Nov 22- Nov 29
Weekly $1700
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.
7BR 5.5BA
Dec 23- Dec 26
$7900
Jan 2 - Jan 12
Weekly $11330
Jan 16- Jan 19
Nightly $2350
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.
6BR 4BA
Oct 8 - Oct 13
Oct 16 - Oct 21
Nov 6- Nov 12
Dec 17- Dec 19
Weekly $5600
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.
5BR 3BA
Oct 11 - Oct 24
Dec 10 - Dec 22
Weekly $6450
Nightly $1175
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.
4BR 3BA
Oct 9 - Oct 13
Oct 29 - Nov 1
Dec 3- Dec 10
Nightly $975
Weekly $4850
Nov 20 - Nov 27
Weekly $6400
Nightly $1200
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.
2BR 2.5BA
Dec 1 - Dec 31
Monthly $5250
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.
2BR 2BA
Oct 9 - Oct 14
Nov 7- Nov 10
Weekly $2600
Nightly $525
Standard Rates: $2190 - $5315 per week
2BR 2BA - Sleeps 4
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.
2BR 2BA
Oct 22 - Oct 30
Weekly $3300
Standard Rates: $1855 - $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.’
2BR 2BA
Oct 16 - Oct 23
Nov 26 - Nov 29
Dec 6 - Dec 9
Nightly $550
Weekly $2600
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.
4BR 3.5BA
Oct 8 - Oct 13
Oct 17 - Oct 21
Nov 22 - Nov 25
Dec 3- Dec 5
Dec 12- Dec 19
Weekly $4650
Nightly $825
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.
2BR 2BA
Oct 8 - Oct 13
Oct 16 - Oct 21
Nov 6- Nov 12
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.
4BR 4BA
Oct 5- Oct 13
Oct 16 - Oct 20
Nov 14 - Nov 20
Nov 27 - Dec 1
Dec 5 - Dec 10
Dec 15- Dec 21
Weekly $4650
Nightly $825
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.
3BR 2BA
Oct 8 - Oct 13
Oct 16 - Oct 21
Nov 6 - Nov 12
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.
1BR 1BA
Oct 10 - Oct 13
Nightly $450
Oct 22- Oct 30
4- 8 nights $2800
Nov 5- Nov 7
Nov 14- Nov 19
Nov 26 - Nov 29
Dec 16 - Dec 20
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 Duval. Romantic 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.
3BR 2.5BA
Oct 15 - Oct 20
Weekly $2650
Nightly $575
Oct 24 - Oct 31
Weekly $3600
Nightly $700
Oct 31 - Nov 9
Dec 14- Dec 18
Weekly $2650
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.
4BR 4BA
Oct 10 - Oct 13
Dec 12 - Dec 20
Weekly $5200
Nightly $975
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."
2BR 2BA
Oct 17 - Oct 22
Nightly $550
Weekly $2650
Nov 18- Nov 26
Weekly $3600
Nightly $650
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.
3BR 2.5BA
Oct 10 - Oct 16
Oct 30 - Nov 4
Weekly $2650
Nightly $575
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."
4BR 4BA
Oct 17 - Oct 23
Nov 14 - Nov 19
Dec 3 - Dec 8
Nightly $975
Weekly $5200
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.
4BR 4BA
Oct 10 - Oct 14
Nov 7 - Nov 10
Nightly $975
Weekly $5200
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.
2BR 2BA
Oct 17 - Oct 23
Nov 27 - Dec 1
Weekly $2975
Nightly $650
Nov 20 - Nov 27
Weekly $3400
Nightly $700
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.
