Key West ~ Vacation Rentals

Below are Weekly & Monthly Rentals with no specified number of bedrooms and no specified arrival or departure date.

* 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. However, if you are able to adjust your arrival or departure date we may be able to make it work. Please contact our office and let us do the work for you. info@vhkw.com or 305-294-7358 ext. 1

There is a minimum stay requirement of 30 days or 1 calendar month for monthly rentals. If you are having trouble finding an available rental please contact our office and let us do the work for you. info@vhkw.com or 305-294-7358 ext. 1


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

A whole vacation experience for the entire family. Rent the whole 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!

Monthly Rental Rates:
Winter - $25000 / mo - Shoulder - $18000 / mo - Summer - $18000 / mo

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new property
seaport treasure estate

2BR 2BA
Private Pool and bricked courtyard
Sleeps 2-6
Duval St. 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. 

 

Weekly Rental Rates:
Winter - $2950 / wk - Shoulder - $2600 / wk - Summer - $2250 / wk

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caribbean cottage ~ duval street key west

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

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.

Weekly Rental Rates:
Winter - $8900 / wk - Shoulder - $7850 / wk - Summer - $6900 / wk

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island rendezvous

4BR 3BA - Sleeps 8-10
Heated Pool - Sun Deck
Lush Pool Garden
Just Off Upper Duval St.

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.

Weekly Rental Rates:
Winter - $5350 / wk - Shoulder - $4500 / wk - Summer - $4200 / wk

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villa deja vu key west

4BR 4BA - Sleeps 8
Famous Mile 0 Location
Entire 2nd FL + back deck on ground level
Downtown - 1 block off Duval St.

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.

 

Weekly Rental Rates:
Winter - $4450 / wk - Shoulder - $4000 / wk - Summer - $3600 / wk

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heavenly hideout at rainbows end

11BR 11BA - Sleeps up to 24
2 heated swimming pools (1 with Jacuzzi jets)
Steps from the 500 block of Duval St.
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. 

Weekly Rental Rates:
Winter - $15675 / wk - Shoulder - $14200 / wk - Summer - $12450 / wk

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the meeting point   key west

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.

Monthly Rental Rates:
Winter - $5500 / mo - Shoulder - $4500 / mo - Summer - $3500 / mo

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elegant key west tree house

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 bone 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.

Weekly Rental Rates:
Winter - $3100 / wk - Shoulder - $2550 / wk - Summer - $2150 / wk

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new property
by the beautiful sea

4BR 3.5BA - Sleeps 10
Heated Pool
Expansive Roof-Top Deck
Steps from Upper Duval St.

"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."

 

Weekly Rental Rates:
Winter - $5700 / wk - Shoulder - $5100 / wk - Summer - $4500 / wk

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amelias hideaway

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

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

 

Weekly Rental Rates:
Winter - $3200 / wk - Shoulder - $2750 / wk - Summer - $2400 / wk

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down island digs

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

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

Weekly Rental Rates:
Winter - $9475 / wk - Shoulder - $8625 / wk - Summer - $7025 / wk

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family reunion

3BR 3BA - Sleeps 6-8
Large roof deck overlooks Duval St.
Covered porch overlooks pool couryard
Heated Pool - Gated courtyard on ground level
Stroll to South Beach

One-of-a-kind privately owned villa-plus- penthouse; Enviable view of Duval Street from private roof-top deck; Premier Down-town Old Town Key West location. If you rent this property, you will have a penthouse and a villa combined into one... and you'll be in the most requested downtown Duval Street location.

Special Promotion ~ Extended Summer Rates ~ June 5 – Dec. 14, 2015

Monthly Rental Rates:
Winter - $10500 / mo - Shoulder - $8500 / mo - Summer - $7500 / mo

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to the nines key west penthouse villa

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

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.”

Monthly Rental Rates:
Winter - $21500 / mo - Shoulder - $12000 / mo - Summer - $12000 / mo

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new property
bella grand premier

4BR 3BA - Sleeps 10
Unique 2 Cottage Design
Heated Pool - Sun Deck
Deck + Balconies

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.

Weekly Rental Rates:
Winter - $5700 / wk - Shoulder - $5100 / wk - Summer - $4500 / wk

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pavilion villa

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

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

Weekly Rental Rates:
Winter - $2626 / wk - Shoulder - $1762 / wk - Summer - $1762 / wk

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new property
original poolside pad

4BR 4BA + (2 1/2 BA) - Sleeps 8
2 Kitchens
Entire 2nd + 3rd floors of the building
Porch overlooks Duval St 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.

Weekly Rental Rates:
Winter - $4450 / wk - Shoulder - $4000 / wk - Summer - $3600 / wk

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penthouse on duval

1BR 1BA - Sleeps 2-4
Duval St.
Hidden pool and courtyard.
2 min. walk to South Beach. Perfect couples retreat.

Vintage Luxury Cottage - An elegant Cottage with Private Heated Pool. "Best Kept Key West Secret."

Weekly Rental Rates:
Winter - $2950 / wk - Shoulder - $2550 / wk - Summer - $2150 / wk

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vintage luxury cottage

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.  

Weekly Rental Rates:
Winter - $5100 / wk - Shoulder - $4500 / wk - Summer - $4100 / wk

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tropical luxury

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.

Weekly Rental Rates:
Winter - $5950 / wk - Shoulder - $4300 / wk - Summer - $4300 / wk

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private key west sunset

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

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

Weekly Rental Rates:
Winter - $5700 / wk - Shoulder - $5100 / wk - Summer - $4500 / wk

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fantasy resort villa

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.

 

Weekly Rental Rates:
Winter - $2200 / wk - Shoulder - $2000 / wk - Summer - $1700 / wk

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secret courtyard cottage quartet

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

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

Weekly Rental Rates:
Winter - $2893 / wk - Shoulder - $2028 / wk - Summer - $2028 / wk

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new property
carriage house cottage

2BR 3BA (One is a Spa Bath)
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 ...

 

Weekly Rental Rates:
Winter - $3100 / wk - Shoulder - $2550 / wk - Summer - $2150 / wk

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exclusive key west beach front

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.

Weekly Rental Rates:
Winter - $5100 / wk - Shoulder - $4500 / wk - Summer - $4100 / wk

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key west wabi sabi

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.

Monthly Rental Rates:
Winter - $9000 / mo - Shoulder - $7500 / mo - Summer - $6000 / mo

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new property
the qm ~ quartermaster house key west

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

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

Monthly Rental Rates:
Winter - $4000 / mo - Shoulder - $3200 / mo - Summer - $2900 / mo

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butterfly garden

2BR 2BA - Sleeps 2-4

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.

 

Weekly Rental Rates:
Winter - $2400 / wk - Shoulder - $2000 / wk - Summer - $1700 / wk

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island oasis garden home

2BR 2BA - Sleeps 4-6
Private Swimming Pool
On Upper Duval St. - 1 min. walk to South Beach.
Great for 2 couples or small family

Open the front door of this hand crafted Key West cottage and look south toward Havana Cuba and you'll catch a view of the ocean where the full moon rises with a soft salt southern breeze.

 

Weekly Rental Rates:
Winter - $3200 / wk - Shoulder - $2750 / wk - Summer - $2400 / wk

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havana moon

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

I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. This is what you’ll experience as you make your entrance to this beautiful Bahamian ‘eyebrow’ style home, nestled away in private back corner of the small Old Town Key West gated community of Windward Park.

 

Weekly Rental Rates:
Winter - $2500 / wk - Shoulder - $2150 / wk - Summer - $1850 / wk

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dancing palms villa

2BR 2.5BA - Sleeps 4-6

An exclusive island style brownstone perfectly nestled in Key West's most prominent gated waterfront neighborhood known as "Truman Annex."

 

Weekly Rental Rates:
Winter - $2900 / wk - Shoulder - $2100 / wk - Summer - $2100 / wk

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island brownstone

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

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

 

Weekly Rental Rates:
Winter - $2500 / wk - Shoulder - $2350 / wk - Summer - $2100 / wk

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cockadoodle cottage

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.

Special Promotion ~ Extended Summer Rates ~ June 5 – Dec. 14, 2015

Monthly Rental Rates:
Winter - $8800 / mo - Shoulder - $6500 / mo - Summer - $5500 / mo

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on hemingways rounds

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.

Weekly Rental Rates:
Winter - $6500 / wk - Shoulder - $6050 / wk - Summer - $4950 / wk

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flower power house

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.

Weekly Rental Rates:
Winter - $2975 / wk - Shoulder - $2575 / wk - Summer - $2075 / wk

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a tropical tradition

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

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

Weekly Rental Rates:
Winter - $2427 / wk - Shoulder - $1629 / wk - Summer - $1629 / wk

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new property
rooftop renaissance

7BR 5BA - Sleeps 12-14
Heated Pool
Lush Tropical Gardens
Famous Historic Seaport neighborhood
Stroll to Duval St.

Classic Key West Estate is one of the few grand centurion wooden estate homes plus pool-side cottage, with private deck and swimming pool, licensed to rent weekly in the Historic Seaport neighborhood. It is located on famous Fleming St. with beautiful curb side appeal.

Weekly Rental Rates:
Winter - $8700 / wk - Shoulder - $7300 / wk - Summer - $6350 / wk

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as seen on house hunters on vacation hgtv
classic key west estate

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.

 

Weekly Rental Rates:
Winter - $2900 / wk - Shoulder - $2100 / wk - Summer - $2100 / wk

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foundry on the waterfront

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

Small pets (under 35 pounds) considered - Restrictions Apply

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

Monthly Rental Rates:
Winter - $5800 / mo - Shoulder - $5100 / mo - Summer - $4600 / mo

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new property
tropical sun garden retreat

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.

Weekly Rental Rates:
Winter - $10475 / wk - Shoulder - $9150 / wk - Summer - $7950 / wk

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grande dame key west

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

A moden interior re-design has thoughtfully transformed a prosaic 'shot-gun' cottage it into the sophisticated 'L-Shape' 4 bedroom 4 bathroom pool-side courtyard Villa Nouveau. Fabulous downtown Key West location just off-Duval St. Rent separate or with Grande Dame Key West - 'The Watson House' estate.

 

Weekly Rental Rates:
Winter - $5700 / wk - Shoulder - $5100 / wk - Summer - $4500 / wk

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villa nouveau key west

1BR 1BA - Sleeps 2-4
Preferred Heart of Old Town neighborhood
Close to the Casa Marina and Higgs Beach. Quiet setting.

Island living is made easy in this classical-contemporary one bedroom, 2-story Key West cottage. The location of our Topsail Cottage Key West  vacation rental, comes with a piece of very unique historical trivia that is interesting to ponder.

Monthly Rental Rates:
Winter - $5500 / mo - Shoulder - $3100 / mo - Summer - $3100 / mo

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new property
topsail cottage key west

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.

Weekly Rental Rates:
Winter - $2225 / wk - Shoulder - $2000 / wk - Summer - $1800 / wk

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city island view

4BR 4BA - Sleeps 8
Dipping Pool w/ Waterfall
Large Hot Tub
Sun Deck
Just off Upper Duval St.

The cottage that grew into a villa ... This proud 1890's 'cigar maker's cottage' has been newly transformed into a stylish contemporary spa-garden 4 BR 4 BA Villa. Captivated by the weirdly wild yet wonderfully elegant Key West life-style, the owner created a fabulous balance of opposites.

Weekly Rental Rates:
Winter - $5700 / wk - Shoulder - $5100 / wk - Summer - $4500 / wk

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key west spa villa

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.

Weekly Rental Rates:
Winter - $3750 / wk - Shoulder - $3250 / wk - Summer - $2950 / wk

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key west dreamin

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.

Weekly Rental Rates:
Winter - $2225 / wk - Shoulder - $2000 / wk - Summer - $1800 / wk

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starlight siesta

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.

 

Weekly Rental Rates:
Winter - $5700 / wk - Shoulder - $5100 / wk - Summer - $4500 / wk

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twice as nice

3BR 2BA - Sleeps 2-8
Outdoor Spa Room
Close to Higgs Beach

Strikingly set in the oft-missed Key West Beachside neighborhood, we find Island Elegance ~ Near the Beach, making a seriously smart curbside statement showing a tall white privacy wall topped with shimmering green louvers. Completely renovated in summer 2012, to modern luxury standards, this island home is a fabulous display of tropical-modern with the perfect touch of Caribbean-Colonial architectural detail.

Monthly Rental Rates:
Winter - $7250 / mo - Shoulder - $6250 / mo - Summer - $5250 / mo

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island elegance ~ near the beach

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.

Weekly Rental Rates:
Winter - $2175 / wk - Shoulder - $2025 / wk - Summer - $1675 / wk

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tree tops

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.

Weekly Rental Rates:
Winter - $2625 / wk - Shoulder - $2425 / wk - Summer - $1975 / wk

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garden suite

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.

 

Weekly Rental Rates:
Winter - $6850 / wk - Shoulder - $5900 / wk - Summer - $4800 / wk

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tropical tranquility

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.

Weekly Rental Rates:
Winter - $7500 / wk - Shoulder - $6200 / wk - Summer - $5200 / wk

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the caroline house

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.

Monthly Rental Rates:
Winter - $25000 / mo - Shoulder - $18000 / mo - Summer - $18000 / mo

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new property
ultimate key west beach house  sunset key ~ vip

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.

Weekly Rental Rates:
Winter - $4800 / wk - Shoulder - $4450 / wk - Summer - $3650 / wk

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amandas dream suites

2BR 2BA - Sleeps 2-4
Heated Pool - Sun Deck
Historic Seaport neighborhood - Steps from the Harbor

Located steps from the Historic Seaport property is in one of the most charming and interesting Old Town residential neighborhoods of Key West. A low-key curb appeal makes a huge surprise when walk in and see the great room open to the fabulous swimming pool and deck in the back yard. 

Monthly Rental Rates:
Winter - $8500 / mo - Shoulder - $7200 / mo - Summer - $5550 / mo

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port side perfection

4BR 3BA + Library-Office
Swimming Pool
Spacious Private Back Deck and Courtyard
Center of Old Town Key West. Close to Dvual St.

Neatly situated between a fashionably narrow island street and a hidden lane, this "house-plus-guest-cottage" villa displays a West Indies design that smoothly melds a sophisticated British Colonial gracefulness with a carefree Caribbean flare. The overall effect both warms the heart and tickles the soul with a fanciful-folly-of-charm.

Monthly Rental Rates:
Winter - $10500 / mo - Shoulder - $8500 / mo - Summer - $8500 / mo

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key west indies

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.

Monthly Rental Rates:
Winter - $5800 / mo - Shoulder - $5100 / mo - Summer - $4600 / mo

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governors retreat

3BR 2.5BA - Sleeps 6
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.

Monthly Rental Rates:
Winter - $8000 / mo - Shoulder - $6300 / mo - Summer - $5250 / mo

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mediterranean caribbean villa

3BR (+Den) 3.5BA - Sleeps 6-7
Free-form heated pool - spacious sun deck
Close to Higgs beach in stylish White Street Gallery neighborhood

Live in the lap of luxury in this stunningly renovated Key West classic "Eyebrow House." An esteemed Key West renovation builder assembled a creative team of elite woodworkers, masons, local craftspeople, and an internationally known traveling artist sailor to execute his plans.

Monthly Rental Rates:
Winter - $9000 / mo - Shoulder - $7500 / mo - Summer - $6000 / mo

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