Key West Vacation Condos
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  • (305) 294-7358
Key West Time
January 23rd
9:06am · 72°F

Key West ~ Vacation Condos

Condos - A condo or town-house is one of a row of private houses joined by common sidewalls in a planned complex of two or more buildings. A condo or townhouse is an individually owned apartment style unit in a complex with a commonly owned grounds. Most condos and townhouses have two to three bedrooms.

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

dancing palms villa
special rates available

Jan 23- Jan 30
Weekly $2375

Mar 3- Mar 31
Weekly $2675

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Standard Rates: $1850 - $3475 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.


cabana boheme

Standard Rates: $3950 - $9500 per month

Small Gated Garden Compound
Shared Pool w/ Trickling Waterfall
Newly Constructed in Traditional Design
Private Covered Parking
On Block Off Duval St.

Center to the common gardens, a brick path winds through a hidden courtyard, leading to an alluring pool with trickling waterfall. This is what creates the "ah ... feeling." So relaxing yet only a  block from boho Upper Duval St., in Old Town Key West.


truman treasure

Standard Rates: $2600 - $5600 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.

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

Jan 24- Jan 27
Nightly $425

Mar 17- Mar 24
Weekly $2900

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Standard Rates: $1800 - $3900 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.

island brownstone
special rates available

Mar 11- Mar 29
Weekly $2900

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Standard Rates: $1900 - $3900 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.’

original poolside pad

Standard Rates: $1762 - $3151 per week

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.

private key west sunset

Standard Rates: $3800 - $7000 per week

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.

exclusive key west beach front

Standard Rates: $1800 - $3900 per week

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 ...


a tropical tradition
special rates available

Feb 3- Feb 10

Mar 10- Mar 17
Weekly $2875

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Standard Rates: $1750 - $3670 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.

foundry on the waterfront

Standard Rates: $1800 - $3900 per week

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.


cocos poolside retreat
special rates available

Jan 31 - Feb 7
Feb 11- Feb 17
Feb 24- Mar 17
Weekly $2800
Nightly $450

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Standard Rates: $1750 - $3670 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."

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Sunset Key

sunset key






town houses and condos