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August 13th
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Key West ~ Vacation Homes

View our exclusive Key West vacation rentals. Vacation Homes of Key West can help you find the perfect vacation rental for your next Key West vacation. Don't pay booking fees, save money by booking directly with VHKW today.

* PLEASE NOTE: Some properties displayed may not be available for rent due to other inquiries and pending reservations. 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


dancing palms villa
special rates available

2BR 2Ba

Weekly $3150

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Standard Rates: $2535 - $5145 per week

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

Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs. This is what you’ll experience as you make your entrance to this beautiful Bahamian ‘eyebrow’ style home, nestled away in private back corner of the small Old Town Key West gated community of Windward Park.

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elegant key west tree house
special rates available

2BR 1BA

Aug 9- Sept 30

Monthly $4200

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Standard Rates: $3750 - $7350 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.

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designer octagon house of key west
special rates available

4BR 4BA

Aug 15- Oct 31

Monthly
$20,000

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Standard Rates: $25000 - $40000 per month

4BR 4.5BA - Sleeps 8
Famous Iconic Victorian Estate
Extraordinary Designer Home
Expansive Resort-Style Gardens
Large Swimming Pool
Wrap-around Verandahs

Standing prominently in the sought-after Key West Historic Seaport Neighborhood, this iconic designer octagon Victorian house is often feaured in notable architectural publilcations. Purchased and restored by superstar designer Angelo Donghia in 1976, and purchased in 1981 by famous designer Calvin Klein, it raised the bar on historic home renovation in Key West. Today is stands as a phenomenal paradise home with luxury designer decor and 5-Star amenities. Truly an amazing historic and top-of-the-line place to stay in Key West.

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casa bella petite le bleu
New

Standard Rates: $6000 - $15000 per month

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family reunion

Standard Rates: $9205 - $21280 per week

12BR 8 Full BA and 2 Half BA
Sleeps 28
Large swimming pool in tropical garden
Boho-beautiful main house
Two side-by-side townhouses
Walk to Higgs Beach.
Close to White Street shopping
Great value.

"Family's who play together, stay together." This is a spacious Key West rental for your family reunion vacation. Property includes: a main house and attached cottage suite decorated with a bohemian shabby chic flair, and two townhouses situated in a spacious tropical garden, and large swimming pool.

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sunset serenade

Standard Rates: $7950 - $18500 per month

2BR + Office 2.5 BA
Sleeps 4 - 6
Private Roof Top Viewing Deck
White Sandy Beaches
Garden Oasis Swimming Pool
Private Tropical Resort Island

You’re one click closer to a private island paradise. Sunset Serenade can put you right there.  Here you’re softly serenaded with the sounds of the surrounding sea and rustling fronds of the palm trees, while you chill-out on your own private rooftop deck to enjoy the changing colors of the tropical sky.

 

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little digs key west
special rates available

1BR !BA



Monthly $3500

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Standard Rates: $3000 - $5500 per month

1 BR 1 BA
Sleeps 2 - 3
Luxury Interior Upgrades
Solares Hill Neighborhood
Center of Old Town
5 Minute Walk to Duval Street

Diminutive in size but huge in style, Little Digs Key West, authenticates how ‘big things’ really do happen in small spaces. Spacious design. A complete luxury makeover of this 1933 historic cottage. It sits in proud harmony with other historic residential cottages, on a narrow one-way lane in the middle of Old Town Key West. 

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bella grand premier estate

Standard Rates: $22000 - $38800 per month

5BR 5.5BA - Sleeps 10
Grand Luxury Estate on 7,500 Sq Ft Lot
2-Story Guest House + 2-Story Main House
Deluxe Zen-Garden Pool with Pool Bridges
Steinway Upright Piano
Premier Street in Center of Old Town
Gated and Private
5-Star Quality Experience

Deluxe Old Town Key West estate with a new twist on history. Premier custom design reflects the historic neighborhood, while reinventing the Key West luxury lifestyle. Zen-garden swimming pool, trickling tiled waterfalls and a spa. Wide stone bridges built over the pool sleekly connect the houses together. A remarkable home to experience with family and friends. 

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seaport hideaway
New
special rates available

2BR 1.5BA

Sept 20 - Oct 31

Monthly $4500

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Standard Rates: $4750 - $8850 per month

2BR 1.5BA
Sleeps 2 - 4
Limited Edition 2-Story Condo
2 Streets from Historic Seaport
Private Porches and Courtyard Garden
Hidden from View in Heritage Building

Magic happened when this Key West wooden heritage building was redesigned. Now offers limited-edition condominiums. A case in point is this 2BR 1.5BA Seaport Hideaway. Architecturally intriguing. Epic historic atrium stairwell. Masterfully tucked away on Fleming Street. A special residence ideally located 2 short blocks from the docks, at the Key West Historic Seaport neighborhood.

 

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villa corazon
New

Standard Rates: $8000 - $16000 per month

3BR 3BA
Private garden with heart-shaped pool
Luxury renovation with upscale furnishings
Private Guest Cottage in Garden
Casa Marina Neighborhood
Close to Higgs Beach

There’s lots to love about the luxurious 3BR 4BA Villa Corazonit even has a heart shaped pool. Experience ultimate resort style living in this private home retreat. A perfect pairing of a renovated Key West gingerbread cottage with an elegant free-standing cottage that are seamlessly joined with a tropical pool-garden.The interior is a harmonious sweet spot between modern aesthetics and laid-back Caribbean. 

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island rendezvous

Standard Rates: $6455 - $15850 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.

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hidden story book cottage
special rates available

1BR 1BA

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Standard Rates: $3200 - $5700 per month

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

Tucked away down a short walking path in the Center of Old Town Key West, this precious 1BR 1BA Hidden Story-Book Cottage is completely hidden from the street. Comfortable as it is adorable, it even offers a fenced in yard. Perfect for one or two people, here you can set up home and live as a local for a month or more - or settle in to work remotely.

 

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the grand marshall
New

Standard Rates: $11700 - $32800 per month

5BR 4.5 BA - Sleeps 10
2 Heated Swimming Pools
2 Upscale Renovated Houses w/ Fenced Backyards that border each other.
1/2 Block from the Hemingway House & Museum
1 block off Duval Street

If you plan to stay with your family or friends, but treasure your own place to retreat,The Grand Marshall offers the perfect layout. A back-to-back combination of 2 upscale renovated and beautifully decorated historic homes. Around the corner from the Hemingway Home and Museum, one block off Duval St. Settle in for a month or more and become thoroughly relaxed and ‘islandized.’

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key west poolside loft
New
special rates available

2BR 2BA

Aug 26 - Sept 30

Monthly $4150

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Standard Rates: $4500 - $8400 per month

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

You know that adage … An unexpected turn can lead to hidden treasures. If there were ever a place that meets that description, it's this 2BR 2BA Key West Poolside Loft. Cleverly tucked away, here you’re in a unique loft-style Key West cottage, with a private deck and beautiful down-look poolside view.

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old town caribbean estate
New
special rates available

10BR 7.5 BA

Aug 22 - Aug 25
Aug 29 - Sept 1
Sept 5 - Sept 8
Sept 11 - Sept 16
Sept 20 - Sept 30
Weekly $9800
Nightly $1700

Dec 23 - Dec 26
$9900

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Standard Rates: $10080 - $22200 per week

10 BR 7.5 BA - Sleeps 18 - 21
Heated Pool
7 BR Main House + 3 BR Guest House
Lush Tropical Gardens
Famous Historic Seaport neighborhood
Stroll to Duval St.

Spacious. Luxurious. Exotic. Old Town Caribbean Estate is a masterful combination of a classic Key West Victorian home with an exotic Caribbean-style guest house. A remarkable place for family and friends to stay together in a Key West weekly rental.

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private island key west beach house  sunset key ~ vip
New

Standard Rates: $18000 - $28000 per month

3BR 4BA Sleeps 6
Epic View from the Pool to the Beach
Private Tropical Resort Island
Garden Connects with White Sandy Beaches

Epic views from the house, to the pool, to the beach. Grand traditional beach house on the private island of Sunset Key. Far enough away that life slows down. White sandy beaches, turquoise ocean, palm trees rustling, birds twittering - peacefulness. 5-Star Resort amenities at your service.

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tropical chill
special rates available

2BR 2BA

Aug 9 - Aug 20
Sept 14 - Sept 24
Weekly $2100

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Standard Rates: $1780 - $3925 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. 

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governors retreat

Standard Rates: $6500 - $19000 per month

3BR 2.5BA - Sleeps 6
Upscale renovation of Historic Home on Picturesque Lane
Private Swimming Pool w/ Sun Deck
1st & 2nd FL Covered Porches
Expansive Porch Room off Master BR
Off-Street Parking
1 Block Off Duval

Governor's Retreat is situated on a less-traveled lane that exudes sought after charm and character. Pictorial 1900’s historic home with upscale renovations and amenities. Exquisite and imaginative décor. Private pool and deck in fenced tropical garden. Multiple sitting porches in the front and back of the house. A block from the Hemingway Home and Museum.  

 

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seaport treasure estate

Standard Rates: $17000 - $31750 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!

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cockadoodle cottage on duval
special rates available

2BR 2BA


Aug 9 - Sept 30
Nightly $475
Weekly $1900




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Standard Rates: $1895 - $4420 per week

2BR 2BA
Sleeps 4 - 6
Great for 2 Couples or Small Family
Jacuzzi Bath Tub
On Charming Upper Duval St.
1 minute walk to South Beach.

Key West cottage architecture has been time-tested in island life and culture in this infamous little wooden 'cigar maker's' cottage located on famous Duval Street, at the 'classier upper-end.'

 

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key west mile zero suite
special rates available

2BR 2BA

Aug 12- Aug 31

Weekly $2700
Nightly $550

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Standard Rates: $2230 - $5315 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!

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butterfly garden
special rates available

1BR !BA
Aug 9 - Sept 30

Monthly $3600

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Standard Rates: $3300 - $5750 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.

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ocean view luxury villa

Standard Rates: $4280 - $10600 per week

3BR 4BA - Sleeps 6-8
Ocean View / Sun Deck
Private Heated Pool
Key West Truman Annex Neighborhood
Short Walk to Beach and Key West Waterfront Park Amphitheater
Pet Friendly

Gorgeous Old Town Key West Ocean View Luxury Home in immaculate gated neighborhood! 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 Duval Street and downtown Old Town Key West..

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key west sunset sojourn
New

Standard Rates: $10600 - $26625 per month

3BR + Media Room 4BA
Sleeps 6
Private Swimming Pool w/ fenced gardens
Private porches off each BR
Private Roof-Top Lookout Deck
White Sandy Beaches
Private Tropical Resort Island

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. 

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

3BR 2BA

Aug 14 - Aug 31
Sept 7 - Sept 20
Sept 24- Oct 1
Weekly $2500
Nightly $550

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Standard Rates: $2115 - $5355 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.

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on hemingways rounds
New

Standard Rates: $5200 - $13800 per month

2BR 2BA - Sleeps 4
Beautifully Renovated 1920 Bungalow
Private Swimming Pool & Sun Deck
Upscale Amenities
On Famous Whitehead St.
1 Block off Duval Street

On Hemingway's Rounds, is an inspired renovation of a classic circa 1920 American Bungalow redone Key West style. Private swimming pool garden and deck in the fenced back yard. Historic front porch with comfy chairs to relax and watch Key west go by. Interior design is imaginative and elegant. Less than one block from the Hemingway Home and Museum. 

 

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exclusive key west beach front
special rates available

2BR 3BA


Aug 20- Sept 17

Weekly $2500

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Standard Rates: $2115 - $5355 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 ...

 

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sweet sunshine garden flat
special rates available

2BR 1BA
Aug 29 - Sept 7
Sept 14 - Sept 30
Weekly $1700

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Standard Rates: $1485 - $3390 per week

2BR 1BA - Sleeps 4
Truman Annex Neighborhood
Steps to Truman Waterfront Park
Shared Heated Pool w/ Caribbean Cabana
2 Blocks from Duval Street
10 minute walk to the waters’ edge of Ft. Zachary Taylor Beach

Sweet Sunshine Garden Flat is perfectly situated for a week near the beach and downtown Old Town Key West. Looking north, you’re less than two blocks from downtown old town – looking south you’re less than two blocks from the Truman Waterfront Park and Fort Zachary Taylor State Park and Beach. 

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classic key west estate
special rates available

7BR 5.5BA

Aug 22 - Aug 25
Aug 29 - Sept 1
Sept 5 - Sept 8
Sept 11 - Sept 16
Sept 20 - Sept 30
Weekly $7500
Nightly $1500

Dec 23- Dec 26
$7900

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Standard Rates: $7310 - $20100 per week

7 BR 5.5 BA - Sleeps 14 - 16
Heated Pool
Lush Tropical Gardens
Famous Historic Seaport neighborhood
Stroll to Duval St.

Classic Key West Estate is a grand centurion home in the Historic Seaport neighborhood. It offers a spacious two-story Victorian home and a private pool side cottage. It's ideally located two blocks from the famous Historic Seaport. 

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island cosmopolitan cottage

Standard Rates: $5300 - $14000 per month

3 BR 2 BA
Sleeps 4 - 6
Historic Cottage
Upscale Renovation and Interior Design
Large Lap-Swimming Pool
Quiet Neighborhood close to White St.
Easy walk to Higgs Beach

An upscale renovation with elegant furnishings, this heritage cottage has all the luxuries you could want and still enjoy the ambiance of staying in an historic Key West property. Mixing a dash of contemporary style with selected cottage pieces, the designer created a unique island style cosmopolitan hide-away in the White Street Gallery district of Old Town Key West. 

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flower power house
special rates available

6BR 4BA


Weekly $5600
Nightly $975

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Standard Rates: $4750 - $11065 per week

6BR 4BA- Sleeps 12+
Attached 1BR Cottage-style Suite
Overlooks Large Tropical Garden & Large Shared Pool.
Boho style. Great value.
Easy walk to Higgs Beach

Boho beautiful, the free-spirited presence of the Key West Flower Power House has much more in common with the 'real Key West'  than the shiny hotels around town. Off the beaten path but close to everything.

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the caroline house
special rates available

5BR 3BA

Aug 14 - Aug 17
Aug 25 - Sept 8
Sept 12 - Sept 19

Weekly $6450
Nightly $1175

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Standard Rates: $5345 - $12625 per week

5BR 3BA Classic Victorian Estate
Sleeps 10
3 BR Main House plus
2.5 BR Caribbean Bungalow
Heated Pool
In-ground Jacuzzi
Large Private Garden

An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West Victorian house plus Caribbean bungalow cottage. Displaying a perfected tropical style the architect and designer artfully intertwined a romantic look-back into architectural history with a superior eclectic cosmopolitan island charm.

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island elegance
special rates available

3BR 3BA

Sept 1- Sept 30

Monthly $5900

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Standard Rates: $5000 - $12800 per month

3BR 3BA - Sleeps 6
NEW Swimming Pool Garden with Spacious Deck installed Fall 2021
Timeless Historic Features
Split-bedroom Design
Tropical Landscaping
Bricked Private Driveway
Close to Key West Beaches on the South Shore

Channeling the island spirit in oft-missed mid-town, this pool-garden home makes an enviable Key West hideaway. Timeless craftsman-colonial architecture. New swimming pool with spacious sun deck. Lush mature tropical landscaping.

Here you live removed from the hubbub, yet close enough to beaches and Old Town. With a luxuious outdoor poolside living room, you may even find yourself making new island rituals of reading, and sipping Cuban coffee or your favorite cocktail on the deck.

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villa deja vu key west
special rates available

4BR 3BA

Aug 28 - Sept 8
Sept 12 - Sept 24

Nightly $975
Weekly $4850

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Standard Rates: $4345 - $10100 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.

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island interlude
special rates available

2BR 2.5BA


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Standard Rates: $3950 - $8950 per month

2BR 2.5BA - Sleeps 4
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. 

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havana moon over duval
special rates available

2BR 2BA

Aug 14 - Aug 19
Aug 23 - Sept 3
Sept 12- Sept 16
Sept 20 - Sept 30
Weekly $2600
Nightly $525

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Standard Rates: $2190 - $5315 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.

 

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key west cottage on the 16th hole
New

Standard Rates: $2950 - $6500 per month

2BR 1.5BA - Sleeps 4
Key West Golf Club Home
Corner Home
Signature View Over looking lake
Covered Wrap-Around Porch
Shared Pools

It's all about the signature view from the living room and spacious wrap-around back porch, that takes this Key West Golf Club cottage-style townhome to a class all on its own. Overlooking the lake at the renowned 16th hole, this property has no neighbors on one side, expanding your view and privacy even more. Now the only question is … "To Tee or Not to Tee." 

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private pool garden villa
special rates available

3BR 2.5BA

Aug 16 - Aug 22
Aug 26- Sept 2
Sept 18- Sept 30

Nightly $750
Weekly $4450


Weekly $4100
Nightly $750

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Standard Rates: $3710 - $6915 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.

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truman treasure

Standard Rates: $2900 - $8375 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.

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island brownstone
special rates available

2BR 2BA

Aug 9 - Aug 18
Aug 25 - Sept 18
Sept 25 - Oct 4

Weekly $2475

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Standard Rates: $1760 - $5255 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.’

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belle maison du port

Standard Rates: $13000 - $29650 per month

3BR 3.5BA
Victorian Home + Private Guest Cottage
Situated in Private Gated Estate
Available from May through October
Large Private Heated Pool
Premier location - Hidden But Only Steps from Historic Seaport 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. It is comprised of a stunningly renovated 2–Story Victorian home, plus an adjoining one-bedroom guest cottage. Large private resort-style swimming pool with spacious sunning deck..

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caribbean cottage ~ duval street key west
special rates available

2BR 2BA

Aug 17 - Aug 21
Sept 6 - Sept 9
Sept 16- Sept 30
Nightly $550
Weekly $2600

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Standard Rates: $2190 - $5220 per week

2BR 2BA
Sleeps 2 - 5
Charming Upper Duval Street
Private Heated Pool and Bricked Courtyard
2 min. walk to South Beach.
Great for 2 Couples or Small Family

Just steps from Duval Street, this unique Key West cottage has an authentic Caribbean ambience plus a private pool with bricked courtyard. Historic construction with original wood planked polished floors, vintage hand-hewn beams, bright blue tile kitchen and Bahama style wooden window shutters. One of the oldest houses in Key West, exudes authentic charm with all the comforts of home. 

 

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key west wabi sabi
special rates available

4BR 3.5BA

Aug 14 - Aug 26
Aug 31 - Sept 30

Weekly $4650
Nightly $825

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Standard Rates: $4195 - $9205 per week

4BR 3.5BA - Sleeps 8
Custom Interior Design
Heated Pool - Sun Deck
Steps from Duval St.

Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic cottage style island living. More spacious than you may think. 2nd floor bedroom and private bath. Each bedroom has a bathroom. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof.

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tree tops
special rates available

2BR 2BA



Nightly $450
Weekly $2500

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Standard Rates: $2060 - $3955 per week

2BR 1BA - Sleeps 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.

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heavenly hideout at rainbows end
special rates available

4BR 4BA

Aug 12- Sept 30
Weekly $4650
Nightly $825

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Standard Rates: $4195 - $9205 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.

 

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garden suite
special rates available

3BR 2BA

Weekly $2800
Nightly $525

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Standard Rates: $2375 - $4720 per week

3BR 2BA - Sleeps 6
Situated in Gated Tropical Garden
Expansive covered porch
Very Large Pool.
Boho Style Decor
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.

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key west island village cottage

Standard Rates: $4050 - $10350 per month

2BR 1.5 BA - Sleeps 2-6
Award Winning Historic Cottage
Private Dipping Pool in Tropical Garden
Great For Small Family
Historic Seaport Neighborhood
5 Minute Walk to Seaport Docks

Story-book charm, originally built in 1860, a restoration won it the coveted Star Award by the Historic Florida Keys Foundation, in 1995. Situated on famous Southard St., in the Historic Seaport neighborhood, its unique character has so captured lovers of Key West homes and gardens, that it’s been featured in two books - Mary Emmerling’s American Country Cottages, 1993, and again in Key West Gardens and Their Stories, Frawley-Holler, 2000.

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vintage luxury cottage on duval
special rates available

1BR 1BA

Aug 17 _ Aug 24
Aug 28 - Sept 17
Sept 11- Sept 17
Sept 24- Sept 30
Nightly $450
Weekly $2275

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Standard Rates: $1970 - $5120 per week

1BR 1BA - Sleeps 2-4
Duval Street
Heated pool in garden courtyard.
2 min. walk to South Beach. Perfect couples retreat.

Vintage Luxury Cottage on DuvalRomantic hideaway. Completely hidden from the street! Private Heated Pool in charming bricked courtyard garden. Expansive covered porches. Nothing else like this extraordinary cottage in Key West.  

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a tropical tradition
special rates available

3BR 2.5BA

Aug 9 - Aug 13

Weekly $2650
Nightly $575

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Standard Rates: $2265 - $5110 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.

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little red pool garden cottage
special rates available

2BR 2BA

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Standard Rates: $3850 - $12100 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.

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amelias hideaway
special rates available

4BR 4BA

Aug 8 - Aug 13
Aug 20 Aug 25
Aug 28 - Sept 2
Sept 6 - Sept 12
Sept 18- Sept 23
Weekly $5200
Nightly $975

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Standard Rates: $4345 - $10100 per week

4BR 4BA - Sleeps 10
Heated Pool
Expansive Roof-Top Deck
Steps from Upper Duval Street

"In-the-know" travelers who return to Key West love to choose the more elegant area of Upper Duval St. as their favorite area to stay ... "Amelia's Hideaway."

 

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down island digs
special rates available

2BR 2BA

Aug 14 - Aug 18
Aug 22 - Sept 12
Sept 25 - Sept 30

Nightly $550
Weekly $2650

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Standard Rates: $2230 - $5720 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.

 

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cocos poolside retreat
special rates available

3BR 2.5BA

Weekly $2650
Nightly $575

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Standard Rates: $2265 - $5110 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."

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tropical tranquility
special rates available

4BR 4BA

Aug 22- Sept 2
Sept 5 - Sept 22

Nightly $1075
Weekly $5600

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Standard Rates: $4490 - $11535 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.

 

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pavilion villa
special rates available

4BR 4BA

Aug 9 - Aug 13
Aug 22 - Aug 25
Aug 29 _ Sept 7
Sept 14 - Sept 22
Sept 25 - Sept 30
Nightly $975
Weekly $5200

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Standard Rates: $4345 - $10100 per week

4BR 3BA - Sleeps 10
Unique 2 Cottage Design
Heated Pool - Sun Deck
Deck + Balconies
1/2 Block Off Duval Street

A Private Tropical Paradise... is the feeling you get when you enter the pavilion of this extraordinary award winning villa just a half block off Duval St. in Old Town Key West. Close to shops, restaurants, museums, Mallory Square. 

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duval street fantasy resort villa

Standard Rates: $4350 - $10100 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. 

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amandas dream suites

Standard Rates: $4430 - $8640 per week

5BR (Den) 3BA - Sleeps 10-12
Bohemian Design and Decor
Large Shared Pool in Tropical Garden
Expansive Porches
Easy Walk to Higgs Beach

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

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twice as nice on duval street
special rates available

4BR 4BA

Aug 14 - Aug 19
Aug 23 - Sept 3
Sept 20 - Sept 30

Nightly $975
Weekly $5200

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Standard Rates: $4400 - $9705 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.

 

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key west dreamin
special rates available

2BR 2BA

Aug 14 - Aug 20
Aug 27 - Sept 9

Weekly $2975
Nightly $650

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Standard Rates: $2600 - $6550 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.

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