Key West Time
April 3rd
2:41am · 81°F
April 3rd
2:41am · 81°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 1.5BA
May 6 - June 17
Monthly $4500
Standard Rates: $4500 - $10309 per month
2BR 1.5BA
Sleeps 2 - 4
Limited Edition 2-Story Condo
2 Streets from Historic Seaport
Private Porches and Courtyard Garden
Hidden from View in Heritage Building
Magic happened when this Key West wooden heritage building was redesigned. Now offers limited-edition condominiums. A case in point is this 2BR 1.5BA Seaport Hideaway. Architecturally intriguing. Epic historic atrium stairwell. Masterfully tucked away on Fleming Street. A special residence ideally located 2 short blocks from the docks, at the Key West Historic Seaport neighborhood.
2BR 1BA
May 1- May 31
Monthly $4450
Standard Rates: $4200 - $8553 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.
2BR 3BA
May 1- May 31
Monthly $11000
Standard Rates: $9900 - $22686 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.
1 BR 2 BA
Apr 20 - May 31
Monthly $4625
Standard Rates: $4625 - $9466 per month
1BR 2BA
Sleeps 2 - 4
Stunning 2-Story Luxury Condo
Hidden in a Heritage Victorian
Private open-air deck
Shared Zen-pool and spa
2 Streets from Historic Seaport
Rooftop Renaissance falls into a unique architectural category of Heritage Victorian - Meets Modern Luxury. This one-of-a-kind monthly rental is situated on the 2nd and 3rd level of a historic Victorian house on Caroline Street. An exquisite 1BR 2BA luxury accommodation, it was redesigned to offer all the accoutrements of a 5-Star condominium.
3 BR 3.5 Baths
May 1- May 31
Monthly $24000
Standard Rates: $20000 - $47374 per month
2BR 2.5BA Sunset Key Villa
Sleeps 4-7
Private Pool
Faces West for sunset
Private beach access
Private resort island
Beautiful nautical themed resort villa on Sunset Key private island. Situated on the western shore for perfect unobstructed view for sunset. Garden gate provides direct access to a white sand private swimming beach.
Welcome to this exeptional nautical themed beach house villa on the private island of Sunset Key. Owned by a world champion sailor the curated decor is reminiscent of cruising the open sea in ultimate comfort. This 2BR 2.5BA home faces west for spectacular evening sunset viewing. It boasts a large private heated swimming pool, direct access to a private swimming beach reserved for only the neighboring few homes, covered outdoor dinint porch and true nautical Key West charm.
4 BR 3.5 Baths
May 10 - May 23
Weekly $6150
Standard Rates: $5500 - $12900 per week
4BR 3.5BA - Sleeps 8
Located in Truman Annex Neighborhood
Waterfront Park Amphitheater
Shared Heated Pool
Short Walk to Beach
Elegant tropical luxury home with impeccable attention to detail. Situated in Key West’s prestigious gated community of Truman Annex! Short walk to Fort Zachary Taylor and Truman Waterfront. Just out the gate to downtown Old Town Key West and Duval Street.
3 BR 3.5 Baths
May 1- May 31
Monthly $12250
Standard Rates: $12000 - $34097 per month
3BR 4BA
Sleeps 6 - 8
Luxury Vacation Villa
Private Pool and Spa
Located in the Heart of Old Town
Beautifully furnished, complete with modern amenities and coastal charm. Each bedroom offers ample space and privacy, with en-suite bathrooms ensuring convenience for all guests. Fully-equipped kitchen, perfect for entertaining.
5BR 5.5Baths
Apr 1- May 31
Monthly $22000
Standard Rates: $23000 - $40345 per month
5BR 5.5BA - Sleeps 10
Grand Luxury Estate on 7,500 Sq Ft Lot
2-Story Guest House + 2-Story Main House
Deluxe Zen-Garden Pool with Pool Bridges
Steinway Upright Piano
Premier Street in Center of Old Town
Gated and Private
5-Star Quality Experience
Deluxe Old Town Key West estate with a new twist on history. Premier custom design reflects the historic neighborhood, while reinventing the Key West luxury lifestyle. Zen-garden swimming pool, trickling tiled waterfalls and a spa. Wide stone bridges built over the pool sleekly connect the houses together. A remarkable home to experience with family and friends.
1BR 1BA
May 1- May 31
Monthly $3900
Standard Rates: $3750 - $6393 per month
1 BR 1 BA
Sleeps 2 - 3
Luxury Interior Upgrades
Solares Hill Neighborhood
Center of Old Town
5 Minute Walk to Duval Street
Diminutive in size but huge in style, Little Digs Key West, authenticates how ‘big things’ really do happen in small spaces. Spacious design. A complete luxury makeover of this 1933 historic cottage. It sits in proud harmony with other historic residential cottages, on a narrow one-way lane in the middle of Old Town Key West.
2 BR 2 BA
June 1- June 30
Monthly $11500
Standard Rates: $9900 - $22686 per month
2BR + Office 2.5 BA
Sleeps 4 - 6
Private Roof Top Viewing Deck
White Sandy Beaches
Garden Oasis Swimming Pool
Private Tropical Resort Island
You’re one click closer to a private island paradise. Sunset Serenade can put you right there. Here you’re softly serenaded with the sounds of the surrounding sea and rustling fronds of the palm trees, while you chill-out on your own private rooftop deck to enjoy the changing colors of the tropical sky.
1BR 1BA
May 1- May 31
Monthly $3900
Standard Rates: $3850 - $6579 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.
2 BR 1 Bath
May 1- May 31
Monthly $4900
Standard Rates: $4500 - $10138 per month
2BR 1BA
Sleeps 2 - 4
Upscale Renovation
Colorful Caribbean Ambience
Adorable Curb Appeal
Most Requested Old Town Key West Neighborhood
Close to Historic Seaport
Beautiful and imaginative one-and-a-half-story shot-gun cottage ideally situated in Old Town Key West. Enchanting as can be, feng shui elements were also used in both the renovation and decorating, to achieve a calming and relaxing ambience.
2BR 2BA
Mar 30 - Apr 2
Apr 14- Apr 19
Nightly $680
Standard Rates: $2580 - $6350 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
Mar 30 - Apr 4
Apr 8 - Apr 22
Nightly $535
Weekly $2695
Standard Rates: $2095 - $4900 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
Apr 1- Apr 10
Apr 20- Apr 25
Nightly $900
Weekly $4900
Standard Rates: $5900 - $12620 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.
3BR 2BA
Mar 15- Mar 17
Apr 10 - Apr 14
Apr 18- Apr 22
Apr 27 - Apr 30
Nightly $625
Standard Rates: $2580 - $5950 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
April 19 - May 31
Weekly $3100
Standard Rates: $2580 - $5950 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
May 8 - May 24
Weekly $1900
Standard Rates: $1800 - $3785 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
Mar 22 - Apr 3
Apr 6- Apr 12
Apr 20 - Apr 24
Nightly $2500
Weekly $13000
Standard Rates: $12390 - $25975 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 2.5BA
Apr 1- May 13
May 19 - June 30
Monthly $5100
Standard Rates: $4900 - $10474 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.
2 BR 2 BA
May 1- May 31
Monthly $7400
Standard Rates: $6500 - $15786 per month
2BR 2BA - Sleeps 4
Beautifully Renovated 1920 Bungalow
Private Swimming Pool & Sun Deck
Upscale Amenities
On Famous Whitehead St.
1 Block off Duval Street
On Hemingway's Rounds, is an inspired renovation of a classic circa 1920 American Bungalow redone Key West style. Private swimming pool garden and deck in the fenced back yard. Historic front porch with comfy chairs to relax and watch Key west go by. Interior design is imaginative and elegant. Less than one block from the Hemingway Home and Museum.
2BR 2BA
Apr 9 - Apr 12
Apr 26 - Apr 29
May 2 - May 5
Nightly $575
Weekly $2900
Standard Rates: $2475 - $5995 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.
3BR 3BA
May 1- May 31
Monthly $6850
Standard Rates: $6450 - $14690 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.
4BR 4BA
May 1 - May 31
Monthly $19000
Standard Rates: $18000 - $36000 per month
4BR 4BA
Sleeps 8
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
Apr 6 - Apr 19
Apr 27 - May 1
Nightly $975
Weekly $5500
Standard Rates: $5250 - $11405 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
May 3 - May 11
May 21 - May 26
Weekly $4400
Nightly $825
Standard Rates: $4245 - $7415 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.
2 BR 1 BA
Apr 1- Apr 10
Apr 20 - Apr 24
Nightly $500
Weekly $2300
Standard Rates: $2200 - $4480 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.
7BR 5.5BA
Mar 22- Apr 3
Apr 6- Apr 12
Apr 20 - Apr 24
Nightly $2300
Weekly $11000
Standard Rates: $9190 - $25975 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.
4BR 3.5BA
Apr 11 - Apr 16
Nightly $975
Weekly $5700
Standard Rates: $1025 - $9950 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
Apr 2- Apr 11
Weekly $7500
Nightly $1400
Standard Rates: $6645 - $13710 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
Mar 30- Apr 2
Apr 6- Apr 9
Apr 14- Apr 19
Nightly $925
Weekly $5500
Standard Rates: $1025 - $9950 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
Apr 5 - Apr 16
Apr 20 - Apr 24
Nightly $975
Weekly $5500
Standard Rates: $5250 - $11405 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
Apr 6- Apr 12
Nightly $650
Standard Rates: $2445 - $5820 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.
3BR 2.5BA
Apr 7 - Apr 9
Apr 22- May 2
Nightly $625
Weekly $3200
Standard Rates: $2695 - $5830 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
Apr 21 - Apr 23
Nightly $900
Standard Rates: $5250 - $11405 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
Apr 5- Apr 11
Nightly $580
Six Nights $2850
Standard Rates: $2390 - $5700 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.
4BR 4BA
Apr 9 - Apr 12
May 11 - May 16
Nightly $850
Standard Rates: $5245 - $10800 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
May 5 - May 14
Nightly $725
Weekly $3900
Standard Rates: $3035 - $7385 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.
