Key West Time
October 3rd
6:01am · 82°F
October 3rd
6:01am · 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.
2 BR 3BA
Sept 30 - Nov 30
Monthly $8500
Dec 1 - Jan 7
Monthly $14000
Standard Rates: $9500 - $20500 per month
2BR + Office 3 BA
Sleeps 4
Private Roof Top Viewing Deck
White Sandy Beaches
Garden Oasis Swimming Pool
Private Tropical Resort Island
Sunset Sonnet Luxury Villa provides an exclusive private island experience with all the amenities of resort living. A colonial - modern 2-story private luxury home. Wrap around porches overlooking pool gardens. Manicured beaches, tennis, award winning restaurant close by, 5-Star amenities. Experience the peace of living on a tiny island with no cars. To stay on Sunset Key is to be in secluded surroundings, just a 15-minute ferry ride from downtown Key West.
1BR 1BA
Sept 30 - Nov 30
Monthly $3700
Standard Rates: $3600 - $5975 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.
2BR 2BA
Sept 29- Oct 10
Oct 31 - Nov 16
Weekly $2100
Standard Rates: $2165 - $4140 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.
2BR 2BA
Sept 21 - Oct 10
Nightly $500
Weekly $2575
Standard Rates: $2230 - $6030 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!
2BR 2BA
Sept 26 - Oct 20
Nightly $450
Weekly $1900
Oct 27 - Oct 31
Nightly $675
Standard Rates: $1895 - $4640 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.'
6BR 4BA
Oct 1- Oct 5
Oct 8 - Oct 12
Oct 16- Oct 21
Oct 28 - Nov 5
Weekly $4900
Nightly $900
Standard Rates: $4750 - $11670 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.
1BR !BA
Sept 30- Nov 30
Monthly $3850
Standard Rates: $3700 - $6050 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
Sept 24 - Oct 10
Nightly $550
Weekly $2400
Oct 25 - Oct 30
Fantasy Fest
Nightly $635
Oct 30 - Nov 6
Nightly $550
Weekly $2400
Standard Rates: $2580 - $5625 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 21 - Oct 7
Oct 30 - Nov 6
Weekly $2500
Oct 21- Oct 29
Fantasy Fest
Weekly $3500
Standard Rates: $2530 - $5625 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
Sept 21 - Oct 9
Weekly $1700
Oct 25 - Nov 1
Fantasy Fest
Weekly $2600
Standard Rates: $1485 - $3575 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.
10BR 7.5 BA
Oct 6 - Oct 14
Nov 11 - Nov 18
Nightly $1900
Weekly $8900
Oct 28 - Nov 4
Fantasy Fest
Nightly $2200
Weekly $11000
Dec 23- Dec 27
Four nights $12900
Standard Rates: $10080 - $23420 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 2- Oct 6
Weekly $2200
Nightly $550
Oct 27 - Nov 1
Nightly $750
Standard Rates: $2190 - $5600 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 16 - Oct 23
Weekly $2350
Standard Rates: $2500 - $5520 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.’
3BR 3BA
Nov 1 - Nov 30
Monthly $6500
Standard Rates: $5750 - $13400 per month
3BR 3BA - Sleeps 6
NEW Swimming Pool Garden with Spacious Deck installed Fall 2021
Timeless Historic Features
Split-bedroom Design
Tropical Landscaping
Bricked Private Driveway
Close to Key West Beaches on the South Shore
Channeling the island spirit in oft-missed mid-town, this pool-garden home makes an enviable Key West hideaway. Timeless craftsman-colonial architecture. New swimming pool with spacious sun deck. Lush mature tropical landscaping.
Here you live removed from the hubbub, yet close enough to beaches and Old Town. With a luxuious outdoor poolside living room, you may even find yourself making new island rituals of reading, and sipping Cuban coffee or your favorite cocktail on the deck.
3BR 4BA
Sept 30 - Nov 30
Monthly $16500
Standard Rates: $15000 - $29500 per month
3BR + Media Room 4BA
Sleeps 6
Private Swimming Pool w/ fenced gardens
Private porches off each BR
Private Roof-Top Lookout Deck
White Sandy Beaches
Private Tropical Resort Island
Imagine the ultimate Key West dream home that feels like a faraway oasis - where you can watch crowning tropical sunsets from a private rooftop deck. Someplace truly extraordinary, elegant yet also comfortable – a sojourn on a private island surrounded by sparkling turquoise waters and balmy breezes.
4BR 3BA
Sept 28- Oct 14
Oct 17 - Oct 22
Oct 30 - Nov 6
Nightly $950
Weekly $4900
Oct 22- Oct 30
Fantasy Fest
Nightly $1250
Weekly $6400
Standard Rates: $5250 - $10650 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.
3BR 2.5BA
Oct 8 - Oct 13
Oct 20 - Oct 23
Oct 30 - Nov 8
Nightly $725
Weekly $3900
Standard Rates: $4245 - $6950 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.
2BR 2BA
Oct 1- Oct 5
Oct 8 - Oct 12
Oct 16-Oct 21
Nightly $450
Weekly $1900
Standard Rates: $2060 - $4170 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.
7BR 5.5BA
Oct 6 - Oct 14
Nov 11 - Nov 18
Nightly $1700
Weekly $7900
Oct 28 - Nov 4
Fantasy Fest
Nightly $1800
Weekly $9000
Dec 23- Dec 27
Four nights $12000
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.
3BR 2BA
Oct 1- Oct 5
Oct 8 - Oct 12
Oct 16-Oct 21
Weekly $2550
Nightly $500
Standard Rates: $2375 - $5170 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.
4BR 3.5BA
Sept 26 - Oct 11
Oct 15 - Oct 20
Nightly $775
Weekly $4500
Nov 19 - Nov 27
Nightly $985
Weekly $5500
Standard Rates: $4195 - $9700 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.
5BR 3BA
Oct 1- Oct 7
Oct 14 - Oct 23
Nightly $1175
Weekly $5950
Standard Rates: $5345 - $13310 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 4BA
Sept 28 - Oct 10
Weekly $4500
Nightly $775
Nov 6 - Nov 17
Nov 20 - Nov 27
Nightly $985
Weekly $5500
Standard Rates: $4195 - $9700 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.
4BR 4BA
Sept 28 - Oct 3
Oct 17 - Oct 22
Nightly $875
Weekly $4900
Oct 27 - Nov 5
Fantasy Fest
Nightly $1025
Weekly $5900
Standard Rates: $4345 - $10650 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
Sept 30 - Oct 7
Oct 15 - Oct 22
Oct 29 - Nov 6
Nightly $525
Weekly $2375
Standard Rates: $2190 - $5500 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 4BA
Dec 16 - Dec 21
Five Nights $4500
Nightly $1025
Jan 12- Jan 15
Nightly $1375
Standard Rates: $4490 - $12170 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.
3BR 2.5BA
Sept 30 - Oct 4
Oct 16- Oct 22
Oct 29 - Nov 5
Nightly $525
Weekly $2500
Standard Rates: $2265 - $5390 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 3BA
Sept 30 - Oct 5
Nightly $875
Weekly $4900
Dec 23- Dec 26
Nightly $1325
Standard Rates: $4345 - $10650 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.
1BR 1BA
Oct 21-Oct 29
Fantasy Fest
Weekly $3500
Nightly $685
Oct 30 - Nov 4
Nightly $525
Standard Rates: $1970 - $5400 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.
2BR 2BA
Sept 30 - Oct 6
Oct 17 - Oct 21
Nightly $525
Weekly $2375
Standard Rates: $2230 - $6030 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.
4BR 4BA
Oct 27 - Nov 1
Nightly $1475
Standard Rates: $4400 - $10150 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
Sept 30 - Oct 4
Nov 20 - Nov 24
Nightly $600
Weekly $2875
Standard Rates: $2600 - $6900 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.
