Key West Weekly Vacation Rentals
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September 24th
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Key West ~ Weekly Vacation Rentals

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Below are Weekly Rentals with no specified number of bedrooms

Key West weekly rentals hold a special City of Key West transient license which allows these properties to be rented weekly or nightly. Most weekly rentals have a minimum stay of 3 to 5 nights and during some months require a week minimum stay.

Weekly rentals are decorated Key West island style, reflecting the unique tastes of property owners. Some are furnished luxuriously, and some more simply. All are equipped with essential amenities and conveniences of home, including internet, TV, linens, and kitchenware. Read our property descriptions to learn the details.

* PLEASE NOTE: Some properties displayed may not be available for rent due to other inquires and pending reservation. Please contact our office to be sure of availability. info@vhkw.com or 305-294-7358 ext. 1

There are no properties available that fit all of your search options. Please contact our office if you would like assistance. info@vhkw.com or 305-294-7358 ext. 1


island rendezvous

Standard Rates: $5500 - $11575 per week

6BR 5BA - Sleeps 14
2 heated swimming pools
3 Cottage Compound (2-cottage villa plus a cottage).
Less than 1/2 block off Duval Street

Get together for an 'Island Rendezvous' in Key West in this Award Winning Villa and Caribbean Style Cottage side-by-side steps from Duval St. and 3.5 Blocks from Mallory Square. Perfect solution for a gathering of family or friends for a week in paradise.


flower power house

Standard Rates: $3950 - $8100 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.


truman treasure
New

Standard Rates: $2600 - $5600 per week

3BR 2.5BA - Sleeps up to 5
Stroll to the Beach
Truman Annex residence with Ocean View from Bedroom Balconies
Short Walk to all Downtown Old Town Key West Features

Rent this Key West Luxury Home and Experience a Remarkable Piece of American Architectural History. A renovated 'Truman Treasure', in one of the most desirable Ocean Front Old Town Key West locations.


heavenly hideout at rainbows end
special rates available


Sept 19- Oct 5
Oct 8- Oct 17
Weekly $3900
Nightly $675

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Standard Rates: $2900 - $6700 per week

4BR 4BA - Sleeps 8
Famous Mile 0 Location
1 block off Duval Street.
Custom Interior Design
Private Heated Pool starting August 1, 2017
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.

 


the meeting point   key west

Standard Rates: $10350 - $20170 per week

11BR 11BA - Sleeps up to 24
2 heated swimming pools (1 with Spa Jets)
Steps from the 500 block of Duval Street
3-story historic Victorian home plus new 4 BR villa

"Let's stay together ... for a week or more." Start calling your family and make a plan. If you’re looking for luxury and plenty of room, The Meeting Point Key West is the grandest vacation rental licensed to rent weekly in Key West, both in stature and style. 7 BR 7 Full BA elegant Victorian Mansion plus 4 BR 4 Full BA luxury villa. 


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


Oct 22-Oct 29
Weekly $2250

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Standard Rates: $1800 - $3900 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.


key west mile zero suite

Standard Rates: $1500 - $4000 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 starting August 1, 2017
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!


island brownstone
New

Standard Rates: $1900 - $3900 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.’


amelias hideaway
special rates available


Sept 16- Sept 27
Weekly $3900
Nightly $800

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Standard Rates: $3600 - $7400 per week

4BR 3.5BA - 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."

 


family reunion

Standard Rates: $5700 - $11770 per week

9BR + Dens 6.5BA - Sleeps 22
Large swimming pool in tropical garden. Walk to Higgs Beach and stylish White St. gallery neighborhood. Boho beautiful main house plus renovated condo. Great value.

"Family's who play together, stay together." This is a spacious Key West rental for your family reunion vacation. Property includeds a main house and attached cottage suite decorated with a bohemian shabby chic flair, plus a renovated condo. Why not gather in a gated complex with a home, plus private attached cottage, and town home situated in a spacious garden, and large swimming pool.


cockadoodle cottage
special rates available


Sept 8- Oct 4
Weekly $1900
Nightly $325

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Standard Rates: $1700 - $3225 per week

2BR 2BA (with Jacuzzi Bath Tub) - Sleeps 4-6
On Upper Duval St. - 1 min walk to South Beach.
Great for 2 couples or small family.

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.'

 


dancing palms villa
special rates available

Sept 16- Sept 30
Weekly $1650.00

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Standard Rates: $1850 - $3475 per week

2BR 2BA - Sleeps 4
Manicured Tropical Swimming Pool Garden
Shared Heated Pool
Walk to Duval St. in 3 minutes

I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. 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.

 


original poolside pad

Standard Rates: $1762 - $3151 per week

1BR 1BA - Sleeps 2-3
Private Back Deck and garden
Shared Pool
Special Resort Amenities Gratis

Beautifully situated in a significant wooden red Cyprus wood building which is an accurate replica of the 1880’s Alfonso Cigar Factory, this Original Poolside Pad is not only rich in history but big on service amenities and comfort.


key west wabi sabi
special rates available


Sept 11- Sept 15
Sept 23- Oct 5
Weekly $3900
Nightly $700

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Standard Rates: $3500 - $6700 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.


penthouse on duval

Standard Rates: $2900 - $6000 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.
Adult Location

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.


private key west sunset

Standard Rates: $3800 - $7000 per week

3BR 3BA
Private Balcony - Key West Sunset View

Key West sunsets are famous ... holding a perfect perch overlooking the entrance to Key West Harbor, this spacious luxury condominium gives you a wonderful balcony to celebrate sunset in private.


caribbean cottage ~ duval street key west
special rates available


Sept 4- Sept 10
Oct 17- Oct 22
Weekly $2100
Nightly $375

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Standard Rates: $1850 - $3800 per week

2BR 2BA
Duval Street
Private Heated Pool and Bricked Courtyard
Sleeps 2-5
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 feel plus a private pool with bricked courtyard, with original wood planked polished floors, vintage hand-hewned 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. 

 


exclusive key west beach front
special rates available


Sept 2- Sept 20
Weekly $1900
Nightly $450





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Standard Rates: $1800 - $3900 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 ...

 


villa deja vu key west
special rates available


Sept 4-Sept 9
Sept 16-Sept 23
Sept 30- Oct 5
Oct 9- Oct 22
Weekly $3900
Nightly $750

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Standard Rates: $3500 - $7400 per week

4BR 3BA - Sleeps 8
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.


down island digs
special rates available



Oct 27- Oct 30
$1500

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Standard Rates: $1900 - $4175 per week

2BR 2BA - Sleeps 2-6
1/2 block off Duval Street
Unique large private manicured pool-side garden.

Everything about "Down Island Digs" adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street.

 


key west spa villa
special rates available



Sept 17- Sept 22
Weekly $3900
Nightly $700

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Standard Rates: $3600 - $7400 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.


tropical tranquility
special rates available


Sept 17- Sept 23
Weekly $4500
Nightly $1000

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Standard Rates: $3900 - $8500 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.

 


private pool garden villa

Standard Rates: $3200 - $5100 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.


vintage luxury cottage
special rates available



Oct 7-Oct 12
Weekly $1950
Nightly $375

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Standard Rates: $1800 - $3725 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. "Best Kept Key West Secret."


a tropical tradition
special rates available


Sept 17- Sept 28
Oct 16- Oct 22
Nightly $375
Weekly $1800

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Standard Rates: $1750 - $3670 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.


pavilion villa
special rates available



Sept 24 -Oct 1
Oct 14-Oct 20
Weekly $3900
Nightly $700

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Standard Rates: $3600 - $7400 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.


classic key west estate
special rates available


Oct 15- Oct 21
Nightly $1100
Weekly $6200

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Standard Rates: $5400 - $12100 per week

7BR 5BA - 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.


secret courtyard cottage quartet

Standard Rates: $1475 - $2800 per week

2BR 1BA - Sleeps 2-5
Private Renovated Cottage
Private Jacuzzi Tub
Steps from Duval St.

Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this hideaway, you'll never know you're right in the center of Old Town Key West.

 


foundry on the waterfront

Standard Rates: $1800 - $3900 per week

2BR 2.5BA - Sleeps 4-6

A striking tri-level condominium situated in Key West's most historic gated waterfront luxury neighborhood offers a beautiful combination of classic historic charm and refined modern ambience.

 


grande dame key west   the watson house

Standard Rates: $6750 - $12920 per week

7BR 7BA - Sleeps 16
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.


tropical luxury
special rates available


Sept 18- Sept 22

Nightly $700
Weekly $3900

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Standard Rates: $3500 - $6700 per week

4BR 3BA - Sleeps 7-8
Heated Free-Form Pool - Sun Deck
Heart of Old Town Key West - Preferred Heart of Old Town neighborhood

Old-world charm meets modern tropical luxury in this wonderful historic island home. Built of original glistening heart pine from floor to ceiling, the interior rooms radiate a warm and magical feel. The grounds offer a classic front sitting porch, and generous size resort style back deck with custom free-form swimming pool.  


havana moon
special rates available

Sept 12- Oct 4
Weekly 2150
Nightly $400

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Standard Rates: $1900 - $4175 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

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.

 


fantasy resort villa

Standard Rates: $3600 - $7400 per week

3BR 3BA - Sleeps 8
Just Off Upper Duval Street
Private Adjoining Cottages
with 2 Private Pools

This one-of-a-kind island villa perfectly blends two charming historic cottages right into a little bit of Old Town Key West island heaven. Your own private tropical resort is the feeling you get when you enter the bricked courtyard.


carriage house cottage

Standard Rates: $2028 - $3700 per week

2BR 1BA - Sleeps 2-5
Private Front Porch
Shared Pool
Special Resort Amenities Gratis

If you’ve been to Key West, chances are you’ve passed by the Carriage House Cottage without taking notice. But that’s not for lack of artistic charm or historic interest. Rather, it is the ubiquitous arch framing the 1800’s horse carriage pass-through that would have caught your eye.


cocos poolside retreat

Standard Rates: $1750 - $3670 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."


twice as nice
special rates available

Sept 12- Oct 4
Weekly $3900
Nightly $750

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Standard Rates: $3600 - $7400 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.

 


city island view

Standard Rates: $1500 - $3500 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.


rooftop renaissance

Standard Rates: $1629 - $3152 per week

1BR 1BA - Sleeps 2 - 3
Grand Private Front Porch with Bird’s Eye View
Shared Swimming Pool
Special Resort Amenities Gratis

Rooftop Renaissance cottage flat creates the special feeling of being hidden away in secret quarters. Tucked up in the tree tops on the end of a grand historic building, there is no way you would know there was a charming one bedroom cottage with a deep room-size private porch extending the entire width of the building.


starlight siesta
special rates available


Oct 15- Oct 21
Weekly $1750
Nightly $350

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Standard Rates: $1500 - $3500 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.


villa nouveau key west
special rates available


Oct 8- Oct 13
Weekly $3900
Nightly $750

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Standard Rates: $3600 - $7400 per week

4BR 4BA - Sleeps 8
Heated Pool
Private Sun Deck
Steps from Duval St.

A moden 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.

 


tree tops

Standard Rates: $1675 - $2855 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.


garden suite

Standard Rates: $1975 - $3419 per week

3BR 2BA - Sleeps 6
Garden Suite
Vacation Rental
Large covered porch steps to large tropicial garden with very large shared pool. Boho style. 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.


key west dreamin

Standard Rates: $2300 - $4800 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.


the caroline house

Standard Rates: $4500 - $9250 per week

5BR 3BA Classic Victorian House - Sleeps 10
Plus 2BR 1/2 story Caribbean Bungalow
Heated Pool
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.


lazy iguana
special rates available


Sept 24- Oct 13
Nightly $650
Weekly $3900

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Standard Rates: $3500 - $6600 per week

Large Private Swimming Pool
with Spacious Outdoor Cabana
4BR 3.5BA Main house plus Studio Cottage
Sleeps 8

During the months of May through January 2,  this genuine Key West combo of our Private Pool Garden Villa plus a classy private studio cottage that adjoins the property can be your very own get-away.


amandas dream suites

Standard Rates: $550 - $6275 per week

4-5BR (Den) 3BA - Sleeps 8-12
Bohemian Design and Decor
Large Shared Pool in Landscaped Garden
Expansive Porches
Easy Walk to Higgs Beach

Originally built in the 1938, this charming large wooden home has two full stories with deep porches which overlook the garden and pool. The floor plan was redesigned with an exterior staircase so it can also be utilized as two separate units.

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