Key West Time
January 17th
8:50pm · 70°F
January 17th
8:50pm · 70°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.
1 BR 2 BA
Mar 1- Mar 31
Monthly $8150
Standard Rates: $4900 - $9150 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.
1BR 1BA
Mar 1- Mar 31
Monthly $5200
Standard Rates: $3750 - $6180 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.
2BR 2 Bath
Mar 1 - Mar 31
Monthly $15500
Standard Rates: $7500 - $18500 per month
2BR 2BA - Sleeps 4
Award Winning Historic Cottage
Gorgeous Interior Re-design
Swimming Pool
First impressions are everything. And its love at first glance with this Old Town Key West cottage. The 2BR 2BA Casa Bella Petite le Bleu is a luxurious charming pool-garden home. Situated on the quiet upper end of famous Elizabeth Street, this stylish house is filled with authentic charm.
The impressive renovation of this 18th Century wooden cottage earned it the coveted Historic Florida Keys Foundation Preservation Award. It provides off-street bricked parking with a Tesla charging station.
An ideal cottage for 2 to 4 people, if more people decide to join you in Key West - No Problem! Right across the street is the extraordinary 5BR 5.5 BA Bella Grand Premier Estate.
2BR 2BA
Jan 26- Jan 31
Feb 9 - Feb 14
Weekly $4200
Nightly $850
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 2 - Mar 15
Nightly $650
Weekly $3400
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
Jan 26 - Jan 30
Feb 2 - Feb 5
Feb 14 - Feb 22
Nightly $1400
Weekly $6500
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
Jan 28 - Feb 4
Nightly $650
Weekly $3500
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 1BA
Mar 15-Mar 22
Weekly $2700
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
Feb 10 - Mar 1
Nightly $2800
Weekly $15500
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 2BA
Mar 8 - Mar 12
Nightly $650
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.
4BR 3BA
Jan 26- Feb 6
Feb 10 - Feb 14
Nightly $1200
Weekly $5900
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.
2 BR 1 BA
Jan 26 - Jan 30
Feb 2 - Feb 5
Feb 14- Feb 22
Nightly $450
Weekly $2100
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
Feb 10 - Mar 1
Nightly $2600
Weekly $13000
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.
3 BR 2 BA
Jan 26- Jan 30
Feb 2- Feb 5
Feb 14- Feb 22
Nightly $625
Weekly $2900
Standard Rates: $2800 - $5580 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
Jan 25- Jan 27
Nightly $875
Feb 8 - Feb 15
Nightly $975
Weekly $5650
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
Mar 23- Mar 30
Weekly $9900
Nightly $1800
Standard Rates: $6645 - $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
Jan 26- Jan 31
Feb 9 - Feb 14
Weekly $6500
Nightly $1100
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
Feb 2- Feb 6
Feb 10 - Feb 15
Feb 22- Mar 1
Nightly $1200
Weekly $5900
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
Jan 27 - Jan 30
Mar 3- Mar 8
Nightly $575
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
Jan 27 - Jan 30
Nightly $650
Feb 9 - Feb 15
Feb 22 - Feb 28
Nightly $750
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."
1 1/2 BR 1BA
Standard Rates: $4875 - $11600 per month
2BR 1.5 BA - Sleeps 2-6
Award Winning Historic Cottage
Private Dipping Pool in Tropical Garden
Great For Small Family
Historic Seaport Neighborhood
5 Minute Walk to Seaport Docks
Story-book charm, originally built in 1860, a restoration won it the coveted Star Award by the Historic Florida Keys Foundation, in 1995. Situated on famous Southard St., in the Historic Seaport neighborhood, its unique character has so captured lovers of Key West homes and gardens, that it’s been featured in two books - Mary Emmerling’s American Country Cottages, 1993, and again in Key West Gardens and Their Stories, Frawley-Holler, 2000.
4BR 3BA
Feb 16- Feb 20
Nightly $1100
Feb 24- Mar 1
Nightly $1200
5 nights $5400
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
Mar 2 - Mar 8
Mar 15 - Mar 18
Nightly $750
Six Nights $3850
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.
2BR 2BA
Jan 25 - Jan 28
Jan 30 - Feb 1
Nightly $675
Standard Rates: $2580 - $6435 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.
2BR 2BA
Mar 1- Mar 10
Weekly $5200
Nightly $875
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.
