pinterest facebook instagram twitter youtube google my business
  • (305) 294-7358
COVID-19 INFO
Key West Time
July 30th
3:26pm · 89°F
 
 

Vacation Rental Discounts and Special Rates

* 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.


hidden story book cottage
special rates available

July 22 - Aug 31

Monthly $3375


Standard Rates: $3200 - $5600 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.

 


penthouse on duval
special rates available

Aug 23 - Aug 26
Aug 30 - Sept 3
Sept 19 - Sept 22

Nightly $700


Standard Rates: $2940 - $7915 per week

4BR 4BA + (2 1/2 BA) - Sleeps 8
2 Kitchens
Entire 2nd + 3rd floors of the building
Porch overlooks Duval Street in the 700 Block.
Spacious deck in the back.

Perfectly staged on Duval Street Key West, this unique downtown Key West rental received a major renovation to become the  fabulous "Penthouse On Duval." Stroll to South Beach and Mallory Square. Plenty of room to spread out. Enviable Fantasy Fest location!  Mallory Square and the beach.


key west spa villa
special rates available

Aug 10 - Sept 7
Weekly $4200
Nightly $850


Standard Rates: $3900 - $10225 per week

4BR 4BA - Sleeps 8
Dipping Pool w/ Waterfall
Over-size Hot Tub
Private Sun Deck
Just off Upper Duval Street

Relax, Rejuvenate, Revive. When you rent this 'Key West Spa Villa,' outdoor lounging beside this unique spa garden deck puts a whole new spin on things. And when you're ready to take in Duval St., all you need to do is walk around the corner.

 


by the beautiful sea ~ a key west beach front condo
special rates available

Aug 20 - Aug 27
Sept 2- Sept 11

Weekly $2000
Nightly $450


Standard Rates: $2030 - $5190 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.


villa nouveau key west
special rates available

Aug 21- Aug 26
Aug 30- Sept 2
Sept 11- Sept 16

Nightly $850


Standard Rates: $4270 - $10220 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.

 


cockadoodle cottage on duval
special rates available

Aug 28 - Sept 7
Weekly $1800
Nightly $400


Standard Rates: $1575 - $4310 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.'

 


sweet sunshine garden flat
special rates available

September 5 - October 5
Monthly $4455


Standard Rates: $1295 - $3345 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. 


villa deja vu key west
special rates available

Aug 21- Aug 25
Aug 28- Sept 3
Sept 7- Sept 11
Sept 15- Sept 18

Nightly $850


Standard Rates: $4060 - $10220 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.


private pool garden villa
special rates available

Aug 15- Aug 31
Weekly $3400
Nightly $725


Standard Rates: $3120 - $6660 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.


grande dame key west   the watson house
special rates available

Aug 21- Aug 26
Aug 30- Sept 2
Sept 13- Sept 16

Nightly $1675


Standard Rates: $7560 - $17220 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.


flower power house
special rates available

Aug 22- Aug 26
Aug 29- Sept 3

Nightly $875


Standard Rates: $4200 - $10730 per week

6BR- 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.


dancing palms villa
special rates available

Aug 14- Aug 21
Aug 21- Aug 28
Aug 28- Sept 4
Sept 18- Sept 25

Weekly $2275


Standard Rates: $1855 - $4995 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.


key west wabi sabi
special rates available

Aug 15 - Aug 20
Aug 24 - Aug 31

Weekly $3800
Nightly $800


Standard Rates: $3500 - $8970 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.


city island view of duval street
special rates available

Aug 23 - Aug 26
Aug 30 - Sept 3
Sept 19 - Sept 22

Nightly $400


Standard Rates: $1470 - $4575 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.


island brownstone
special rates available

Aug 21 - Aug 28
Weekly $1800


Standard Rates: $1760 - $4970 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.’


heavenly hideout at rainbows end
special rates available

Sept 4 - Sept 10
Sept 14 - Sept 18
Six Nights $3650
Nightly $800


Standard Rates: $3500 - $8970 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.

 


starlight siesta on duval st lane
special rates available

Aug 23 - Aug 26
Aug 30 - Sept 3
Sept 19 - Sept 22

Nightly $400


Standard Rates: $1470 - $4585 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.


pavilion villa
special rates available

Aug 28 - Sept 2
Sept 20 - Sept 23

Nightly $850


Standard Rates: $4060 - $10220 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. 


the caroline house
special rates available

Sept 20- Sept 24
Nightly $1000


Standard Rates: $5075 - $12760 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.


key west dreamin
special rates available

Aug 7-Aug 10
Aug 31- Sept 3

Nightly $500


Standard Rates: $2415 - $6975 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.


cocos poolside retreat
special rates available

Aug 14 - Aug 19

Nightly $450


Standard Rates: $1995 - $4975 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."

Sort Properties


Rental Period



Vacation Rentals

Rentals For
Social Distancing

rentals for social distancing

Sunset Key

sunset key

Villas

villas

Cottages

cottages

Condos

town houses and condos

Compounds

compounds

Penthouses

penthouses

Estates

estates

Truman Annex

truman annex

Golf Club Vacation Rentals

key west golf club