Key West Time
November 26th
9:15pm · 77°F
November 26th
9:15pm · 77°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.
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.
Dec 2 - Dec 12
Weekly $1900
Nightly $400
Standard Rates: $1900 - $4375 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.
Nov 28 - Dec 3
Dec 6 - Dec 12
Nightly $750
Dec 27 - Dec 30
Nightly $800
Standard Rates: $3850 - $8190 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.
Dec 2 - Dec 12
Weekly $2900
Standard Rates: $3120 - $6315 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.
Standard Rates: $1900 - $4375 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 ...
Dec 19 - Jan 19
Monthly $14,250
Standard Rates: $7500 - $17000 per month
4BR 3BA - Sleeps 8
Modernistic 3BR Home + Studio Cottage
Premier Resort-Style Living
Upscale Minimalist Interior
Private Heated Pool
Multi-level decks / bricked courtyard
Rooftop with panoramic views
Avant-garde home melds flawlessly with a free-standing luxury studio cottage via private pool-garden. Minimalist interiors, floor to ceiling windows, architectural ceilings, sleek built-in cabinetry, Viking chef’s kitchen, all enhance the clean modernistic design. A unique signature to Key West resort-style contemporary living.
Nov 29 - Dec 11
Weekly $3750
Nightly $800
Dec 19 - Dec 25
6 nights = $5500
Standard Rates: $3850 - $7800 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.
Nov 23 - Nov 30
Dec 4 - Dec 14
Weekly $1200
Nightly $275
Standard Rates: $1400 - $2800 per week
1 BR 1 BA
Sleeps 2 - 4
(maximum of 2 adults and 2 children)
Secluded Free-Standing Cottage
Private Sun / Dining deck
Exclusive gated pool garden w/ 7 other cottages
10 Minute Walk to Duval Street
Whether you are looking for a secluded getaway with a central base to explore, or the perfect location for a romantic get-away, this pool-side cottage will be home away from home. So, close your eyes for a few moments, and imagine tropical Key West, and this charming cottage just waiting for you.
Dec 2 - Dec 12
Weekly $1100
Standard Rates: $1295 - $2660 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.
Dec 19 - Dec 23
Nightly $900
Standard Rates: $3500 - $7140 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.
Nov 26 - Dec 5
Weekly $4000
Nightly $875
Standard Rates: $4175 - $9135 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.
Feb 10 - Feb 13 = $6000
Standard Rates: $7050 - $13685 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.
Nov 20 - Nov 28
Weekly $1800
Standard Rates: $1855 - $3710 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.
Nov 21- Nov 30
Weekly $1800
Dec 19 - Dec 26
Weekly $2900
Standard Rates: $1575 - $3500 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.'
Dec 9 - Dec 18
Weekly $3200
nightly $700
Dec 19-Dec 26
Weekly $5900
Standard Rates: $3500 - $7140 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.
Dec 13 - Dec 18
Nightly $1000
Standard Rates: $6575 - $12810 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.
Dec 16 - Dec 19
Nightly $375
Dec 19 - Dec 26
weekly $3500
Standard Rates: $1900 - $4410 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.
Dec 1 - Dec 11
Dec 14 - Dec 18
Weekly $3900
Nightly $800
Standard Rates: $3850 - $8190 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."
Standard Rates: $1470 - $3640 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.
Jan 5- Jan 30
Weekly $2600
Standard Rates: $1800 - $4130 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."
Dec 1 - Dec 11
Weekly $1600
Standard Rates: $1750 - $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.’
Nov 20 - Nov 30
Dec 13 - Dec 20
Weekly $1200
Nightly $315
Standard Rates: $1470 - $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.
Dec 19 - Dec 26
Weekly $3400
Standard Rates: $1890 - $4200 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.
Dec 19 - Dec 26
Weekly $6300
Standard Rates: $3465 - $7715 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.
Nov 20 - Nov 30
Weekly $4150
Nightly $850
Standard Rates: $3850 - $7805 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.
Dec 5 - Dec 12
Weekly $1800
Nightly $375
Standard Rates: $1950 - $4340 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.
Dec 2 - Dec 12
Weekly $1600
Standard Rates: $1750 - $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.
Dec 4 - Dec 12
Weekly $1800
Nightly $375
Standard Rates: $1950 - $4340 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."
