Key West Vacation Cottages
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  • (305) 294-7358
Key West Time
August 16th
1:38pm · 88°F

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

island village cottage

Standard Rates: $3300 - $5500 per month

2BR 1BA - Sleeps 2-4
Ground to Roof Designer Renovation
High-End Amenities
Original Artwork
Private Bricked Porch
Tropical Landscaping

Enchanting as can be, this impeccably renovated Key West shot-gun cottage is imaginatively decorated to detail - achieving an authentic colorful Caribbean ambience with calming feng shui elements. Situated in the Heart of Old Town neighborhood, it is just a stroll away from the famous docks lined with restaurants, bars, and shops amidst the schooner yachts and fishing boats.

suite cottage key west
special rates available

Aug 15- Aug 30
Oct 8- Oct 12

Weekly $2400
Nightly $425

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Standard Rates: $1900 - $4250 per week

2BR 2BA - Sleeps 4
Private Heated Pool
Private Sun Deck
Less than 1 Block from Duval St.

An artistic fusion of past meets present provides a decidedly refreshing and modern interpretation of a classic Key West style. On Simonton St., only one short street from the 500 block of Duval Street, on historic Simonton Street, this could be your perfect spot. Rent separate or with Villa Nouveau Key West or Grande Dame Key West - The Watson House estate.


little red pool garden cottage

Standard Rates: $4000 - $5950 per month

2 BR 1 BA
Private Pool
Idyllic Pool-Garden Island Cottage
Close to the Beach on a Lane
Quiet Neighborhood
Sleeps 2 - 4

‘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
special rates available

Aug 18- Sept 27
Oct 4- Oct 21

Weekly $1800
Nightly $375

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Standard Rates: $1700 - $3275 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
special rates available

Aug 16- Oct 21
Weekly $1825

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Standard Rates: $1850 - $3525 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.


hidden story book cottage

Standard Rates: $3200 - $4450 per month

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

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.

butterfly garden

Standard Rates: $3200 - $4200 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.

caribbean cottage ~ duval street key west
special rates available

Aug 18- Aug 23
Aug 26-Aug 30
Sept 3- Sept 13
Sept 16- Sept 22
Weekly $1975
Nightly $425

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Standard Rates: $1850 - $3850 per week

Duval Street
Private Heated Pool and Bricked Courtyard
Sleeps 2-5
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. 


down island digs
special rates available

Sept 8- Sept 13
Sept 23- Sept 27
Sept 30- Oct 7
Weekly $2100
Nightly $400

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Standard Rates: $1900 - $4250 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

Aug 25- Aug 31
Sept 3- Sept 18
Oct 2- Oct 7
Oct 10- Oct 13
Weekly $1800
Nightly $350

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Standard Rates: $1800 - $3800 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

Standard Rates: $1475 - $2850 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
special rates available

Aug 18- Aug 29
Sept 9- Sept 27
Oct 4- Oct 21
Weekly $1950
Nightly $425

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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.


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.

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