Key West cottages & condos

If you’re looking for an exclusive experience – whether it’s a private cottage on a nearby island, or a one-of-a-kind villa near Duval Street… we have it all. Let us know exactly what you’re looking for and our planning experts will provide you with the perfect recommendation (for free.)

 
 
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The Banyan Resort, Cottages in Key West
The Banyan Resort, Cottages in Key West

The Banyan Resort is the ultimate destination for a weekend get-a-way or long term accommodations in our well appointed suites which offer the perfect blend of history and…

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Coconut Beach Resort, Cottages in Key West
Coconut Beach Resort, Cottages in Key West

Hidden from the street, on the quiet side of the island is the perfect blend of old island architecture, lush vegetation and walkways flowing onto white verandahs. Our private pool deck and jacuzzi open onto a small intimate sandy beach.

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Galleon Resort and Marina, Cottages in Key West
Galleon Resort and Marina, Cottages in Key West

Nestled in the heart of Old Town Key West, The Galleon Resort & Marina has been the vacation choice of countless families and couples for over 30 years!

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Sunset Key, Cottages in Key West
Sunset Key, Cottages in Key West

Luxury Oceanfront Cottages located a few minutes by boat from the island of Key West.

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Lazy Lane Cottages

Specializing in Key West Cottages, Suites and Vacation Rental Homes, Lazy Lane Cottages have great locations in Old Town Key West.

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Courtney's Place

Situated off a quiet lane in the heart of the historic district is Courtney's Place Historic Cottages and Inns. Just one and a half blocks from Duval Street and seven blocks from the ocean.

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Villas Key West

Villas Key West offers suites, cottages and rental homes that are well appointed and charming. Decorated in a Caribbean style including artwork of local artists.

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Andrews Inn & Garden Cottages

Formerly a single-family home built in the early 1900's, the Andrews Inn neighborhood is located in the physical center of Old Town Key West.

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Simonton Court

The lushly landscaped two-acre, private compound consists of the two-story Inn, Manor House, Townhouse or Guest House Suites, The Mansion, six cottages and four pools nestled in between.

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Rose Lane Villas

Rose Lane Villas offers one, two & three bedroom suites with kitchens and living rooms. There's private parking for each villa. The pool is lovely and the location is in the heart of old town Key West.

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Looking for something specific?

With over 20 years of experience, we have built relationships not only with service providers, but also hotels, B&B’s, inns, and more. If you have something specific in mind, or would like recommendations personalized on your unique preferences, contact our local planning experts for your customized travel plans.