Key West Vacation Homes
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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


key west spa villa
special rates available

Sep 27- Oct 31
Weekly $3350
Nightly $650

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Standard Rates: $3850 - $7800 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.


exclusive key west beach front
special rates available

Sept 26 - Oct 7
Oct 17 - Oct 31

Weekly $1900
Nightly $400

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Standard Rates: $1900 - $4375 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 ...

 


hidden story book cottage
special rates available

Month of Sept $2700
Month of Oct $3000

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Standard Rates: $3000 - $4700 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.


seaport treasure estate

Standard Rates: $16000 - $26750 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: $5700 - $12845 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.


the meeting point   key west

Standard Rates: $10725 - $21350 per week

11BR 11BA - Sleeps up to 22
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: $3400 - $6025 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.


sunset serenade
New

Standard Rates: $7500 - $15000 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.

 


family reunion

Standard Rates: $8025 - $17815 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.


key west mile zero suite

Standard Rates: $400 - $6155 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: $8000 - $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.


island cosmopolitan cottage
New

Standard Rates: $5000 - $11000 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. 


modernistic key west luxury home
New

Standard Rates: $7500 - $17000 per month

4BR 3BA - Sleeps 8
Modernistic 3BR Home + Studio Cottage
Premier Resort-Style Living
Upscale Minimalist Interior
Private Heated Pool
Multi-level decks / bricked courtyard
Rooftop with panoramic views

Avant-garde home melds flawlessly with a free-standing luxury studio cottage via private pool-garden. Minimalist interiors, floor to ceiling windows, architectural ceilings, sleek built-in cabinetry, Viking chef’s kitchen, all enhance the clean modernistic design. A unique signature to Key West resort-style contemporary living.

 


dancing palms villa
special rates available

Sept 20 - Oct 31
Weekly $1700

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Standard Rates: $1855 - $3710 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.


oceana suite oceana courtyard cottage
New
special rates available

Sept 18- Sept 25
Oct 2 - Oct 23

Weekly $1350

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Standard Rates: $1400 - $2800 per week

1 BR 1 BA
Sleeps 2 - 4
(maximum of 2 adults and 2 children)
Secluded Free-Standing Cottage
Private Sun / Dining deck
Exclusive gated pool garden w/ 7 other cottages
10 Minute Walk to Duval Street

Whether you are looking for a secluded getaway with a central base to explore, or the perfect location for a romantic get-away, this pool-side cottage will be home away from home. So, close your eyes for a few moments, and imagine tropical Key West, and this charming cottage just waiting for you.


sweet sunshine garden flat
New
special rates available

Sept 18 - Oct 7
Oct 14- Oct 31
Weekly $1295

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Standard Rates: $1295 - $2660 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. 


key west wabi sabi
special rates available

Sept 18- Oct 8
Oct 21- Oct 31

Weekly $3400
Nightly $725

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Standard Rates: $3500 - $7140 per week

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

Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof.


penthouse on duval
special rates available

Sept 19- Oct 9
Oct 13 - Oct 27
Weekly $2900
Nightly $625

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Standard Rates: $2940 - $6405 per week

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

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


ultimate key west beach house  sunset key ~ vip

Standard Rates: $16000 - $26750 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.


bella grand premier

Standard Rates: $10000 - $22000 per month

5BR + Den 4BA - 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.”


key west cottage on the 16th hole
New

Standard Rates: $2850 - $5200 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." 


flower power house
special rates available

Sept 18 - Sept 25
Sept 28 - Oct 9
Oct 16- Oct 31
Weekly $4200
Nightly $875

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Standard Rates: $4175 - $9135 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.


the grand marshall house ~ key west
New
special rates available

Months of Sept/Oct
available for a reduced price
Monthly $8500

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Standard Rates: $9000 - $25000 per month

4BR 3BA - Sleeps 8 - 10
Grand Luxury Estate Home
Historic Seaport Neighborhood
Heated Pool w/In-ground Jacuzzi
Propane Fireplace
Wrap-around Verandas

Entertain in grand style in the open living & formal dining room and outdoor pool-side chill-out room. Estate home built from original heart-pine wood, the interior is re-fit to be grand with polished Brazilian tigerwood floors and stunning mahogany open-beams on 12-foot ceilings. Built-in propane indoor/outdoor fireplace. Wrap around covered porches on the 1st and 2nd floor, and multi-level decks and covered porch create outdoor living spaces. 


classic key west estate
special rates available

Sept 18- Sept 30
Oct 12- Oct 17
Oct 24- Oct 31
Weekly $6600
Nightly $1400

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Standard Rates: $6575 - $12810 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.


heavenly hideout at rainbows end
special rates available

Sept 18 - Oct 15
Oct 19 - Oct 31

Weekly $3200
Nightly $625

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Standard Rates: $3500 - $7140 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.

 


grande dame key west   the watson house
special rates available

Sept 23- Sept 29
Oct 6 - Oct 31
Weekly $7500
Nightly $1600
Six Nights $6450

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Standard Rates: $7050 - $13685 per week

7BR 7BA - Sleeps 14
Amazing Historic Luxury Mansion
Heated Pool - Private Sun Deck
Steps from Duval St.

This award winning renovation of a 3 - story Key West mansion is by far one the rarest private estate Key West rentals offered as a single-family vacation home available by the week. Steps from Duval Street.


tropical chill
New
special rates available

Oct 3 -Oct 10
Weekly $1450

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Standard Rates: $1485 - $3100 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. 


key west island village cottage
New

Standard Rates: $3800 - $8700 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.


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

Sept 18- Oct 3

Weekly $1975
Nightly $425

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Standard Rates: $1900 - $4375 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.


the caroline house
special rates available

Sept 20 - Sept 28
Oct 11- Oct 18
Weekly $5000
Nightly $975

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Standard Rates: $4750 - $9695 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.


little red pool garden cottage

Standard Rates: $3600 - $6230 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.


cockadoodle cottage on duval
special rates available

Sept 20 - Sept 26
Oct 8 - Oct 12
Oct 16- Oct 31
Weekly $1500
Nightly $335

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Standard Rates: $1575 - $3500 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.'

 


island interlude
New

Standard Rates: $3700 - $7350 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. 


designer octagon house of key west
New

Standard Rates: $20000 - $30000 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.


butterfly garden

Standard Rates: $3000 - $4430 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.


ocean view luxury villa

Standard Rates: $4280 - $9300 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..


caribbean cottage ~ duval street key west
special rates available

Sept 18 - Oct 3
Oct 10 - Oct 18
Oct 23- Oct 31

Weekly $1950
Nightly $400

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Standard Rates: $1900 - $4410 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. 

 


truman treasure

Standard Rates: $2900 - $6300 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.


island elegance

Standard Rates: $4700 - $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.


island brownstone
special rates available

Sept 18 - Oct 4
Oct 16 - Oct 28
Weekly $1750

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Standard Rates: $1750 - $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.’


amelias hideaway
special rates available

Sept 26 - Oct 3
Oct 21 - Oct 28
Weekly $3900
Nightly $750

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Standard Rates: $3850 - $8190 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."

 


city island view of duval street
special rates available

Sept 19 - Sept 30


Weekly $1450

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Standard Rates: $1470 - $3640 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.


down island digs
special rates available

Sept 26- Oct 10
Oct 24 - Oct 31
Weekly $1800
Nightly $400

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Standard Rates: $2000 - $4690 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

Sept 18 - Oct 1
Oct 17 - Oct 31
Weekly $3900
Nightly $750

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Standard Rates: $3850 - $8190 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.


starlight siesta on duval st lane
special rates available

Sept 19 - Oct 27

Weekly $1450
Nightly $375

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Standard Rates: $1470 - $3650 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.


belle maison du port

Standard Rates: $13000 - $25000 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..


vintage luxury cottage on duval
special rates available

Sept 18 - Sept 25

Nightly $375
Weekly $1800

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Standard Rates: $1800 - $4130 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."


tropical tranquility
special rates available

Sept 20 - Oct 15

Weekly $4100
Nightly $1000

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Standard Rates: $3975 - $8890 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

Oct 6 - Nov 9

Weekly $3200
Nightly $650

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Standard Rates: $3120 - $6315 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.


tree tops

Standard Rates: $1680 - $3655 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.


havana moon over duval
special rates available

Sept 23 - Oct 10
Weekly $1850
Nightly $400

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Standard Rates: $1890 - $4200 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.

 


pavilion villa
special rates available

Sept 18 - Oct 10

Weekly $3900
Nightly $825

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Standard Rates: $3850 - $8190 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.


garden suite

Standard Rates: $1890 - $4115 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.


a tropical tradition
special rates available

Sept 25 - Sept 30

Weekly $1900
Nightly $400

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Standard Rates: $1950 - $4340 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.


duval street fantasy resort villa

Standard Rates: $3850 - $8180 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. 


twice as nice on duval street
special rates available

Sept 23 - Sept 26
Nightly $725
Weekly $3400

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Standard Rates: $3465 - $7715 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.

 


foundry on the waterfront
special rates available

Sept 18 - oct 4
Oct 11 - Oct 31

Weekly $1700

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Standard Rates: $1750 - $3950 per week

2BR 2.5BA - Sleeps 4
Contemporary Interior Design Built in Historic Brick Architecture
Shared Pool in Gated Garden
Short Walk to Fort Zachary Beach
Close to Key West Water Park
Stroll to Downtown Old Town

A striking tri-level condominium situated in Key West's most historic gated Truman Annex waterfront luxury neighborhood, offers a beautiful combination of classic historic charm and refined modern ambience. Perfect location to enjoy the Truman Waterfron Park Ampitheater.

 


the qm ~ quartermaster house key west

Standard Rates: $5500 - $10800 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.


on hemingways rounds

Standard Rates: $4600 - $9600 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.

 


cocos poolside retreat
special rates available

Sept 18 - Oct 10
Oct 16 - oct 31

Weekly $1900
Nightly $400

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Standard Rates: $1950 - $4340 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."


villa nouveau key west
special rates available

Sept 18- Sept 29
Oct 14 - Oct 31

Weekly $4150
Nightly $850

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Standard Rates: $3850 - $7805 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

Sept 26 - Oct 4
Oct 11- Oct 16

Weekly $2200
Nightly $450

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Standard Rates: $2350 - $5390 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.


amandas dream suites

Standard Rates: $3360 - $7310 per week

4-5BR (Den) 3BA - Sleeps 8-12
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.


governors retreat

Standard Rates: $5000 - $6900 per month

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

A Key West luxury cottage in an idyllic retreat setting situated in a manicured garden and swimming pool. Perfectly Renovated and immaculate Key West neighborhood, known as The Meadows. Easy walk to Key West Historic Seaport.