Key West Vacation Rentals
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info@vhkw.com
Key West Time
October 21st
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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

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 - $11775 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


Nov 4- Nov 7
Nov 26- Nov 29
Nightly $800
Weekly $4900

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Standard Rates: $3950 - $8225 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.


heavenly hideout at rainbows end
special rates available


Oct 28- Nov 1
Nov 20- Nov 23
Nov 30- Dec 4
Dec 12- Dec 23
Weekly $3500
Nightly $700

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Standard Rates: $3500 - $6825 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.

 


the meeting point   key west

Standard Rates: $10350 - $20520 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 - $5750 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. Perched among mature tropical trees, the 1200 square foot 2nd floor flat is situated on a quiet road in the exclusive Old Town Casa Marina neighborhood. With a wide wooden covered porch spanning the front of the house, every room still has the original casement windows providing a fabulous look-down view of different garden scenes.


key west mile zero suite
special rates available


Oct 28- Nov 1
Nov 20 - Nov 23
Nov 30 - Dec 4
Dec 12- Dec 23
Weekly $2200
Nightly $400

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Standard Rates: $2500 - $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
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!


sunset sonnet luxury villa

Standard Rates: $10000 - $17000 per month

2BR 2.5BA - Sleeps 6
Private Tropical Resort Island
w/Luxury Amenities
Expansive Wrap-Around Porches
w/Pool-Garden Views
Private Rooftop Viewing Deck
Oasis Swimming Pool
Crescent white sandy beaches

'Turquoise waters surrounding the land, with crowning sunsets in a pastel sky …' Private luxury villa blends airy contemporary island design with access to high end Sunset Key resort amenities. The crowning glory is a private roof top deck where you can steal away and savor the famous Key West sunsets.


suite cottage key west
New
special rates available


Oct 29- Nov 3
Weekly $2400
Nightly $425

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Standard Rates: $1900 - $4250 per week

2BR 2BA - Sleeps 4
Private Heated Pool
Private Sun Deck
Less than 1 Block from Duval St.

An artistic fusion of past meets present provides a decidedly refreshing and modern interpretation of a classic Key West style. On Simonton St., only one short street from the 500 block of Duval Street, on historic Simonton Street, this could be your perfect spot. Rent separate or with Villa Nouveau Key West or Grande Dame Key West - The Watson House estate.

 

tropical chill
New
special rates available

Nov 24-Dec 20
Weekly $1500

Dec 20- Dec 27
Weekly $1800

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Standard Rates: $1500 - $2900 per week

2BR 2BA - Sleeps 4
Overlooks Tropical Swimming Pool Garden
Shared Heated Pool w/ Caribbean Cabana
Truman Annex Neighborhood
Gates lead to Ft. Zachary Taylor Beach, Truman Waterfront, and Downtown Old Town Key West

If you’re looking for a place to chill-out in the tropical warmth of Key West, this cottage-style flat is a wonderful place to relax and take a breather from everyday life. 


island village cottage
New

Standard Rates: $3300 - $5500 per month

2BR 1BA
Sleeps 2 - 4
Upscale Renovation
Colorful Caribbean Ambience
Adorable Curb Appeal
Most Requested Old Town Key West Neighborhood
Close to Historic Seaport

Beautiful and imaginative one-and-a-half-story shot-gun cottage ideally situated in Old Town Key West. Enchanting as can be, feng shui elements were also used in both the renovation and decorating, to achieve a calming yet colorful and authentic Caribbean ambience.

 


family reunion

Standard Rates: $7450 - $15765 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

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.”


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

12/23-12/27
4 nights $1800

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Standard Rates: $1800 - $3975 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.


little red pool garden cottage

Standard Rates: $4000 - $5950 per month

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

‘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

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.


cockadoodle cottage
special rates available

Nov 18- Nov 23
Nov 30 - Dec 3
Dec 10- Dec 16
Weekly $1800
Nightly $375

Jan 2- Jan 8
Jan 20- Jan 24
6 nights $1800
Nightly $400

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Standard Rates: $1700 - $3275 per week

2BR 2BA
Sleeps 4 - 6
Great for 2 Couples or Small Family
Jacuzzi Bath Tub
Charming Upper Duval St. Neighborhood
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.'

 


key west sunset sojourn

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. 


island interlude
New

Standard Rates: $4200 - $7100 per month

2BR 2.5BR - Sleeps 6
Upscale Town home in gated bricked pool-garden courtyard
Shared Dipping pool with waterfall
Around the corner from trendy Petronia Street where you find Blue Heaven
Short Street from entrance to Fort Zachary Taylor Beach

Aspirational, luxurious, well appointed, and whimsical, are four attributes that make this courtyard townhome a lovely place to call home in Key West. Aptly named, Island Interlude, this 2-story property is situated around the corner from one of the most popular transitional urban scenes of Key West. 


penthouse on duval
special rates available

Nov 24- Dec 1
Dec 15- Dec 19
Weekly $3400
Nightly $675

Jan 7- Jan 11
4 Nights $2400
Nightly $725

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Standard Rates: $2900 - $6100 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.


dancing palms villa
special rates available


Nov 20- Dec 1
Weekly $1825

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Standard Rates: $1850 - $3525 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. 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.


hidden story book cottage

Standard Rates: $3200 - $4450 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

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.


island elegance

Standard Rates: $5400 - $9500 per month

3BR 3BA - Sleeps 6
Timeless Historic Features
Split-bedroom Design
Spacious Front Porch
Tropical Landscaping
Bricked Private Driveway
Close to Key West Beaches on the South Shore

Channeling the island spirit in oft-missed mid-town, this home makes a classical curbside statement. Timeless craftsman-colonial architecture, lush mature tropical landscaping.Here you live away from the hubbub, yet close enough to beaches and Old Town. With many places to place a hammock, you may even find yourself making a new daily island ritual of swinging, reading, and sipping wine.


amelias hideaway
special rates available

Oct 30- Nov 2
Nov 18- Nov 23
Dec 10- Dec 13
Nightly $700
Weekly $3700

Jan 3- Jan 9
Six Nights $4200
Nightly $900

Jan 13- Jan 18
5 nights $3500
Nightly $900

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Standard Rates: $3600 - $7500 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 - $4200 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 Butterfly Garden flat provides you with two private entrances off the large gated meditation 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

Nov 13- Nov 17
Nov 24- Nov 28
Dec 12- Dec 15
Nightly $400

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Standard Rates: $1850 - $3850 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 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. 

 


island oasis garden home
New
special rates available

Oct 20- Oct 30
Fantasy Fest
weekly $1700

Nov 13- Nov 20
Weekly $1700

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Standard Rates: $1675 - $3500 per week

2BR 2BA - Sleeps 2-4
1 Block from Duval Street
Oasis pool and hidden courtyard garden.
Private off-street parking

Just as you're inspired by an island oasis, so is this tropical island garden town home, cleverly hidden in the heart of Old Town Key West.

 

truman treasure

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.


key west wabi sabi
special rates available


Oct 28 Nov 1
Dec 16- Dec 22
Weekly $3500
Nightly $700

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Standard Rates: $3500 - $6825 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.


island brownstone
special rates available


Jan 9- Jan 19
weekly $2800
10 nights $3500

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Standard Rates: $1900 - $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.’


down island digs
special rates available

Nov 18- Nov 22
Dec 17- Dec 21
Weekly $2300
Nightly $400

Dec 28- Jan 5
Weekly $4000
Jan 12- Jan 18
6 nights $2500

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Standard Rates: $1900 - $4250 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.

 


villa deja vu key west
special rates available

Nov 18- Nov 23
Dec 9- Dec 13
Weekly $3850
Nightly $700

Dec 16- Dec 26
Weekly $5700
4 Nights $4400

Jan 12- Jan 16
Jan 23- Jan 26
4 nights $3000
nightly $900

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Standard Rates: $3500 - $7500 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.


classic key west estate
special rates available


Nov 26- Nov 29
Dec 11- Dec 21
Weekly $6000
Nightly $1200

Jan 5- Jan 9
Jan 16- Jan 19
Nightly $1200

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Standard Rates: $5900 - $12100 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.


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.


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


Nov 13- Nov 17
Nov 24- Dec 1
Dec 15- Dec 20
Nightly $1400
Weekly $7500

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Standard Rates: $6750 - $13145 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


Nov 19- Nov 28
Dec 5- Dec 8
Dec 15- Dec 22
Weekly $1800
Nightly $350


Jan 6- Jan 12
Jan 23- Jan 26
6 nights $2300
Nightly $450

Jan 23- Jan 27

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Standard Rates: $1800 - $3800 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."


key west spa villa
special rates available


Nov 24- Nov 28
Dec 15- Dec 19
Weekly $3900
Nightly $700

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Standard Rates: $3600 - $7500 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 - $2850 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.

 


exclusive key west beach front
special rates available


Oct 22- Oct 26 fantasy fest
Nov 13- Nov 17
Dec 8- Dec 11
Nightly $400
Wekkly $2025

Jan 4- Jan 8
Nightly $475

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Standard Rates: $1800 - $3975 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 ...

 


tropical tranquility
special rates available

Nov 14- Nov 18
Dec 15- Dec 22
Weekly $3900
Nightly $1100

Jan 5- Jan 9
Jan 23- Jan 26
4 nights $3900
Nightly $1100

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Standard Rates: $3900 - $8575 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 - $5200 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

Nov 18- Nov 23
Nov 30- Dec 8
Weekly $1950
Nightly $425

Dec 23- Dec 26
$1800

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Standard Rates: $1900 - $4075 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.

 


city island view
special rates available


Nov 12- Nov 15
Nov 24- Dec 1
Weekly $1550
Nightly $350

Jan 4- Jan 8

Nightly $400

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Standard Rates: $1550 - $3600 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

Jan 12- Jan 17
5 nights $3500
3/4 nights $3000

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Standard Rates: $3600 - $7500 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.


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 15- Dec 26
weekly $2100
4 nights $1700

Jan 7- Jan 11
Nightly $400

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Standard Rates: $1500 - $3600 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.


fantasy resort villa

Standard Rates: $3600 - $7500 per week

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

Rare one-of-a-kind property, on Duval Street, yet hidden from the street. Two cottages jointed with a bricked courtyard and swimming pool create a secret resort residence. 


a tropical tradition
special rates available


Oct 28- Oct 31
Nov 24- Nov 30
Dec 14- Dec 21
Weekly $1850
Nightly $375

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Standard Rates: $1750 - $3770 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.


foundry on the waterfront

Standard Rates: $1900 - $3950 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.

 


twice as nice
special rates available

Nov 18- Nov 23
Nov 30 - Dec 3
Weekly $3900
Nightly $800

Dec 23- Dec 26
$3000

Jan 2- Jan 8
6 nights $4300
Nightly $900

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Standard Rates: $3600 - $7250 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 - $2925 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.


cocos poolside retreat
special rates available


Nov 22- Dec 1
Dec 8- Dec 22
Weekly $1850
Nightly $375

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Standard Rates: $1750 - $3770 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."


garden suite
special rates available


Nov 4- Nov 7
Nov 26- Nov 29
Nightly $400

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Standard Rates: $1975 - $3500 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 - $9300 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


Oct 30 - Nov 5
Nov 16- Nov 27
Dec 4 - Dec 7
Dec 15- Dec 22
Weekly $4900
Nightly $1100

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Standard Rates: $4500 - $9375 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


Oct 29- Nov 3
Nov 19- Nov 28
Dec 10- Dec 20
Weekly $4500
Nightly $750

Jan 21- Jan 24
Nightly $800

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Standard Rates: $3600 - $7500 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


Nov 25- Nov 28
Dec 11- Dec 15
Nightly $450
Weekly $2500

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Standard Rates: $2300 - $4875 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



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Standard Rates: $3500 - $6700 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 - $6400 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 - $6600 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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