Key West Vacation Rentals
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info@vhkw.com
Key West Time
December 15th
10:14pm · 67°F
 
 

Key West ~ Vacation Rentals

Choose from our inventory of Key West vacation rentals. We offer something for everyone; from charming cottages, to beachfront condos, to luxury estates, to tropical pool-garden homes.

* 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


seaport treasure estate
special rates available

January

Now available due to recent cancellation at a reduced rate of $21000

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Standard Rates: $18000 - $26000 per month

6BR 6.5BA - Sleeps 12
Luxurious Estate ~ 2 Houses plus Guest Cottage = Private Residential Resort
Gated and Grand
Premier Historic Seaport location! Steps from the boardwalk.

A whole vacation experience for the entire family. Rent this estate and live in luxury in the most requested Historic Seaport location in Key West. Three historic dwellings are seamlessly joined to become one private luxury Key West rental estate. A combination of unique design elements impart that elusive je ne sais quoi of island architectural history. Rent the best of Key West!


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
special rates available


Dec 10- Dec 14
Nightly $800

Jan 31- Feb 6
6 nights $5000
Nightly $ 1000

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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


Dec 11- Dec 23
Weekly $3500
Nightly $675

Jan 6- Jan 13
Jan 13- Jan 20
Weekly $3750
Jan 20- Jan 27
Weekly $4000

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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. 


elegant key west tree house

Standard Rates: $3800 - $5650 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.


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



Dec 16- Dec 26
Weekly $2700

Jan 2- Jan 6
Nightly $500

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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
special rates available

Jan 6- Jan 13
Weekly $2550

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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.’


viva la links
New

Standard Rates: $3100 - $6000 per month

3BR 2BA - Sleeps 6
View of the Golf Course Greens
Indoor - Outdoor Great-Room
Private Garden Deck
2 Shared Swimming Pools
Lush Tropical Landscaping
Wild Life Viewing
15 minutes from Old Town

On the Links with a beautiful view, creating a vibrant backdrop for your Key West indoor-outdoor lifestyle experience. Inside, joyful colors from sunshine yellow, to crimson red, to myriad shades of Caribbean Blue, dial in a playful and light-hearted tone. 


island village cottage
New

Standard Rates: $3300 - $5500 per month

2BR 1BA - Sleeps 2-4
Ground to Roof Designer Renovation
High-End Amenities
Original Artwork
Private Bricked Porch
Tropical Landscaping

Enchanting as can be, this impeccably renovated Key West shot-gun cottage is imaginatively decorated to detail - achieving an authentic colorful Caribbean ambience with calming feng shui elements. Situated in the Heart of Old Town neighborhood, it is just a stroll away from the famous docks lined with restaurants, bars, and shops amidst the schooner yachts and fishing boats.


family reunion

Standard Rates: $5700 - $15440 per week

12BR + Dens 8 Full BA and 2 Half BA - Sleeps 28
Large swimming pool in tropical garden. Walk to Higgs Beach and stylish White St. gallery neighborhood. Boho beautiful main house and two town homes. 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, and two town homes situated in a spacious garden, and large swimming pool.


bella grand premier
special rates available

Dec 15- Jan 31
$17500

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Standard Rates: $12000 - $21500 per month

5BR + Den 5BA - Sleeps 12
Extraordinary swimming pool gardens
Famous Elizabeth St. in Historic Seaport Neighborhood
Stroll to Duval Street

Refined and Elegant. Displaying a perfected cosmopolitan flair, the designer has artfully intertwined a look-back into architectural history with a sophisticated contemporary Caribbean charm. Situated on renowned Elizabeth Street, in the historic seaport neighborhood of Old Town, this home is steeped in a colorful lore and seafaring history – so much so, it is sometimes referred to as “the pirate house.”


little red pool garden cottage
New

Standard Rates: $4000 - $5800 per month

2 BR 1 BA
Private Pool
Idyllic Pool-Garden Island Cottage
Close to the Beach on a Lane
Quiet Neighborhood
Sleeps 2 - 4

‘Heads Up’ to all of you incurable romantics who are looking for the perfect Old Town Key West garden cottage retreat close to the beach. Dream worthy and authentic, it’s a little bit like ‘Little Red Riding Hood’s cottage merges with a ‘Fantasy Island’s’ private pool garden,’ and the two are seamlessly blended.


ocean view luxury villa
New

Standard Rates: $5400 - $7900 per week

3BR 4BA – Sleeps 6-8
Ocean View - Walk to Fort Zachary Taylor Beach
Heating Swimming Pool – Sun Deck
Exclusive Truman Annex Neighborhood

If you've been searching for a Key West Ocean View Luxury Home, this could be the place for you! Holding an enviable spot in Key West’s gated community of Truman Annex, this classic home offers an open water view, easy beach access, and is a short walking distance to downtown Old Town.


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.


cockadoodle cottage
special rates available


Dec 16- Dec 23
Weekly $1700
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.'

 


key west sunset sojourn
New
special rates available

Dec 15- Jan 31
$14000

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Standard Rates: $10000 - $17000 per month

2BR + Office 3BA - Sleeps 6
Private Tropical Resort Island
Roof Top Viewing Deck
White Sandy Beaches
Oasis Swimming Pool

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. 


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.


hidden story book cottage

Standard Rates: $3200 - $4350 per month

1 BR 1 BA
Free-Standing Story-Book Cottage
Gorgeous Interior Upgrades
On a Hidden Walking Path
5 Minute Walk to Duval Street
Sleeps 2 – 3

As I stand on the front porch of this little Hidden Story-Book Cottage in the Old Town Key West, I could swear I’m in a neighborhood in the Bahamas on Green Turtle Cay. But as diminutive as it is, impressive interior upgrades that give it a proportionately larger and luxurious feel.


amelias hideaway
special rates available


Dec 10- Dec 22
Nightly $700
Weekly $3600

Jan 6- Jan 13
Weekly $4250
Jan 13- Jan 20
Weekly $4600

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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."

 


butterfly garden

Standard Rates: $3200 - $4100 per month

1BR 1BA - Sleeps 1-2
Historic meditation garden.
Quiet Living Exclusive Casa Marina neighborhood.
Close to Higgs Beach

Completely hidden from the street, this historic Butteryfly Garden flat provides you with two private entrances off the large gated meditatiion garden. A private covered sitting porch outside your front door beckons you to sit in the freshness of the garden and watch for the butterflies.


caribbean cottage ~ duval street key west
special rates available


Dec 13- Dec 23
Weekly $1900
Nightly $375

Jan 17- Jan 27
weekly $2375

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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

Dec 7 - Dec 10
Dec 17- Dec 22
Weekly $1900
Nightly $400





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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 ...

 


dancing palms villa
special rates available

Dec 9- Dec 23
Weekly $1650.00

Jan 13- Jan 20
Weekly $2375

Jan 20- Jan 27
Jan 27- Feb 3
Weekly $2675

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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.

 


key west wabi sabi
special rates available

Dec 13- Dec 23
Weekly $3500
Nightly $700

Jan 16- Feb 3
Weekly $4100

Feb 3- Feb 10
Weekly $5000

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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.


avant garde key west luxury home

Standard Rates: $4950 - $9500 per month

2BR 2.5BA
Sleeps 4
Premier Heart of Old Town neighborhood
Classic architecture / upscale minimalist interior renovation
Private Heated Pool

Extraordinary upscale renovation. Traditional Key West architecture is flawlessly melded with a minimalist contemporary interior. Exotic and calming, this unique home is offers all the best features of classic and modern island living.


villa on the green

Standard Rates: $3100 - $6000 per month

3BR 2BA - Sleeps 6
View of Golf Course
Private Covered Back Deck
2 Shared Swimming Pools
Lush Tropical Landscaping
Wild Life Viewing
15 minutes from Old Town

When you awaken each day, and ponder your plans …

To tee, or not to tee: that is the question.

Whether ‘tis nobler to gaze at the peaceful scenery,

Or to take swings at golf balls on a sea of greens,

And by opposing end them?

To relax: To live the Key West dream. 


down island digs
special rates available


Dec 13 Dec 16

Weekly $1900
Nightly $400

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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.

 


a tropical tradition
special rates available


Dec 10- Dec 14
Nightly $375
Weekly $1750

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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.


villa deja vu key west
special rates available


Dec 16- Dec 26
Weekly $5100

Jan 6-Jan 12
6 nights $3900
Jan 19- Jan 27
8 Nights $4600
Jan 27- Feb 3
Weekly $5075
Feb 3- Feb 10
Weekly $5375

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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.


classic key west estate
special rates available

Dec 11- Dec 20
Nightly $1100
Weekly $5900

Jan 10-Jan 27
Weekly $7875
Jan 27- Feb 3
weekly $8300

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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.


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.

 


belle maison du port

Standard Rates: $13000 - $25000 per month

3BR 3.5BA
Victorian Home + Private Guest Cottage
Available to rent separate from the estate from May through October
Gated and Grand
Large Private Heated Pool
Premier Historic Seaport location. Steps from the boardwalk!

Extraordinary French Caribbean style Victorian home, Belle Maison du Port (Fine Harbor House), is available as a monthly vacation rental from May through November. Situated on the grounds of the Seaport Treasure Estate. Comprised of a stunningly renovated 2 – Story Victorian home, plus an adjoining one-bedroom guest cottage, and large private resort-style swimming pool.


grande dame key west   the watson house
special rates available


Jan 7- Jan 11
Nightly $1400
Jan 18- Jan 27
Weekly $8950
Jan 27- Feb 10
Weekly $9500

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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.


vintage luxury cottage
special rates available


Jan 3- Jan 6

Nightly $350

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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."


key west spa villa
special rates available


Jan 13- Jan 20
Jan 20- Jan 27
Weekly $4600

Jan 27- Feb 7
Weekly $4900

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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.


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.

 


cocos poolside retreat
special rates available

Dec 7- Dec 19
Nightly $375
Weekly $1750

Jan 2- Jan 12
Jan15- Jan 27
Weekly $2550
Nightly $450
Jan 31 - Feb 17
Weekly $2800

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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."


tropical tranquility
special rates available

Jan 2- Jan 13
Weekly $5750

Jan 20- Feb 3
Weekly $6100

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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
special rates available

Jan 10- Jan 27
weekly $3700
nightly $700

Jan 27- Feb 10
Weekly $3900

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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.


havana moon
special rates available

Dec 20- Dec 23
Weekly 1900
Nightly $400

Jan 13- Jan 20
Weekly $2600
Jan 27- Feb 3
Weekly $2900

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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.

 


city island view
special rates available


Dec 13- Dec 23
Weekly $1500
Nightly $350

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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.


pavilion villa
special rates available


Dec 13- Dec 16
Dec 20- Dec 23
Weekly $3600
Nightly $700

Jan 6- Jan 10
Jan 17- Jan 20
Jan 20- Jan 27
Weekly $4800
Nightly $850

Jan 27- Feb 3
Weekly $5100

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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.


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.


tropical luxury

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.  


starlight siesta
special rates available


Dec 13- Dec 16
Weekly $1500
Nightly $350

Jan 15- Feb 3
Weekly $1900

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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.


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.


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.


tropical sun garden retreat

Standard Rates: $4600 - $6400 per month

2BR 2BA - Sleeps 2-4
Private deck and garden
Plus Shared Manicured Swimming Pool Garden
Peaceful Setting

Small pets (under 35 pounds) considered - Restrictions Apply

Everyone dreams of a charming Key West cottage tucked away in a tropical sun garden where flowers and trees flourish around an outdoor living porch all year round.


twice as nice
special rates available



Dec 16- Dec 23

Weekly $3600
Nightly $700

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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.

 


the qm ~ quartermaster house key west

Standard Rates: $6000 - $10000 per month

3BR 2BA - Sleeps 6-7
Private Back Deck and garden
Shared Pool
Special Resort Amenities Gratis

Born in 1925, the Key West Quartermaster House may have found its way from the Bahamas, ‘lock stock and barrel’, during one of the most colorful points in Key West maritime history. Located in the Historic Seaport Neighborhood, today it offers all the comforts of home plus gratis resort amenities.


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.


on hemingways rounds

Standard Rates: $4500 - $9200 per month

3BR 2BA - Sleeps 6
Private Spa Garden with Pool & Waterfall
1/2 block off Duval St.

On Hemingway's Rounds, is an inspired renovation of a classic 1930's ‘American Bungalow’ redone Key West style.  While the street side remains true to the original casual arts-and-crafts form, the interior now boasts an elegant simplicity that meets even the most discerning of modern tastes.

 


the caroline house
special rates available


Jan 6- Jan 27
Weekly $5900
Jan 27- Feb 3
Weekly $6650

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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.


ultimate key west beach house  sunset key ~ vip

Standard Rates: $18000 - $26000 per month

5BR + Den 6BA - Sleeps 10-12
Private Tropical Resort Island
Front Line Ocean Views
White Sandy Beaches
Custom Fantasy Swimming Pool w/ Waterfalls

Sit back, relax, and choose your favorite mesmerizing view from one of the magnificent private decks on this private island property, 500 yards from the ''main island' of Key West.  Unhurried sunrise, serene sunset, warm turquoise waters, and white sandy beaches – from any direction, it’s divine.


villa nouveau key west
special rates available


Dec 13- Dec 19
Weekly $3900
Nightly $750

Jan 2- Jan 13
Weekly $4800
Jan 21- Jan 27
6 nights $4200

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Standard Rates: $3600 - $7400 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.

 


key west dreamin
special rates available

12/7-12/12
Nightly $400

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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.


lazy iguana
special rates available


Jan 10- Jan 15
Nightly $750
Five nights $3200

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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.


governors retreat

Standard Rates: $5000 - $6400 per month

2BR 2BA - Sleeps 4
Serene setting - Large Lap Pool
Manicured Gardens
Old Town Meadows neighborhood
Easy Stroll to Historic Seaport

A luxury cottage in an idyllic retreat settng where you have the use of a manicured garden and swimming pool.  Perfectly Renovated and Immaculate Neighborhood.


mediterranean caribbean villa

Standard Rates: $5500 - $9000 per month

2BR 2.5BA - Sleeps 4
Free-form heated pool - large sun deck
Manicured Tropical Gardens
Close to Higgs Beach and stylish White St.Gallery neighborhood

Tucked behind a breathtaking tropical garden wall and located along one of Key West's most desirable residential streets, this spectacular home reflects a dynamic blend of contemporary Mediterranean and Caribbean architectural design.

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