Key West Vacation Cottages

Key West ~ Vacation Cottages

Cottages - Smaller than a Villa with 'cottage style' architectural details such as planked floors, open beam ceilings, dormered windows, and romantic or antique style decor. Most cottage properties are one or two bedroom abodes and may be 'free standing' or a flat.

Choose from our inventory of Key West vacation rentals. We offer something for everyone; from charming cottages, to beachfront condos, to luxury estates, to tropical pool-garden homes.

* PLEASE NOTE: Some properties displayed may not be available for rent due to other inquires and pending reservation. Please contact our office to be sure of availability. 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. or 305-294-7358 ext. 1

caribbean cottage ~ duval street key west
special rates available

June 5 - June 11, 2016
June 18 - June 24, 2016

view all specials

Standard Rates: $1800 - $3700 per week

Duval Street
Private Heated Pool and Bricked Courtyard
Sleeps 2-6
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. 


cockadoodle cottage

Standard Rates: $1700 - $3175 per week

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.'


dancing palms villa

Standard Rates: $1850 - $3100 per week

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

I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. 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.


island village cottage down the lane ~ off duval st

Standard Rates: $3750 - $6000 per month

2 BR 1 BA
1 1/2 Streets Off Duval Street
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.

down island digs

Standard Rates: $1900 - $4075 per week

2BR 2BA - Sleeps 2-6
1/2 block off Duval Street
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.


vintage luxury cottage
special rates available

May 30 - June 7, 2016

view all specials

Standard Rates: $1800 - $3650 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. "Best Kept Key West Secret."

secret courtyard cottage quartet
special rates available

June 26 - August 13, 2016
$1550 per week

view all specials

Standard Rates: $1475 - $2750 per week

2BR 1BA - Sleeps 2-5
Private Renovated Cottage
Private Jacuzzi Tub
Steps from Duval St.

Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this hideaway, you'll never know you're right in the center of Old Town Key West.


havana moon

Standard Rates: $1900 - $4075 per week

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

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.


carriage house cottage

Standard Rates: $2028 - $3700 per week

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.

butterfly garden
special rates available

June 1 - August 31, 2016
$2700 per month

view all specials

Standard Rates: $3000 - $4000 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 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.

rooftop renaissance

Standard Rates: $1629 - $3152 per week

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.

tropical sun garden retreat

Standard Rates: $4600 - $6250 per month

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.

topsail cottage key west

Standard Rates: $3500 - $7500 per month

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.

Sort Properties

Rental Period

Vacation Rentals

Sunset Key

sunset key






town houses and condos