Key West ~ Vacation Cottages

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


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

2 BR 1 BA
1 1/2 Streets Off Duval St.
Island Cottage on Charming Lane
Sleeps 2 - 6
Great for a couple or small family

Only 1 1/2 short streets off Duval St., this renovated craftsman shot-gun cottage is situated on a charming lane in Old Town Key West, in one of the most interesting Old Town residential neighborhoods of Key West. The charming curb appeal exudes Caribbean island, nestled on an eclectic gentrified tree-lined lane.

Monthly Rental Rates:
Winter - $6000 / mo - Shoulder - $4500 / mo - Summer - $3750 / mo

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new property
island village cottage down the lane

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

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

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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carriage house cottage

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 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 (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

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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rooftop renaissance

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

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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topsail cottage key west

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