Plan your perfect key west escape

Historic Key West Vacation Rentals

Boutique Vacation Rentals in Key West

Welcome to Key West, a sunny and picturesque island town in the Florida Keys. Find yourself in paradise with our luxury Key West vacation rental homes, condos, and cottages. Our properties are mainly located in the Key West Historic District, on the western side of the island. This desirable area (also known as Old Town) has charming architecture, as well as top points of interest. 

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Featured Historic Key West Rentals

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Hear from our happy Guests

5 Star Experience!!

Reviewed on Thursday, June 5, 2025

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Perfect Get Away

Reviewed on Saturday, May 31, 2025

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Margarita Cottage Review

Reviewed on Friday, May 30, 2025

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A Week Exploring The Keys

Reviewed on Friday, May 23, 2025

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Fantastic Private Compound

Reviewed on Wednesday, May 21, 2025

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Good Times!

Reviewed on Sunday, May 18, 2025

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Key West Vibe On Cloud 9

Reviewed on Sunday, May 18, 2025

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Perfect In Paradise

Reviewed on Saturday, May 17, 2025

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Great Trip!

Reviewed on Saturday, May 17, 2025

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Perfect Stay In Old Key West

Reviewed on Friday, May 16, 2025

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Solaris Garden

Reviewed on Wednesday, May 14, 2025

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What's happening in Key West

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Discover the Magic of Key West

2100 Seafood B 2099 Keysaerial B

Relax At Stunning Beaches and Parks & Savor the Flavors of Key West

Soak up the sun, enjoy tranquil ocean views, and explore Key West's lush parks. Indulge in fresh seafood, iconic Key lime pie, and local culinary gems.

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2102 Events B 2103 Exploreactivities B

Discover Exciting Things to Do & Experience Iconic Events

From water sports to sunset cruises, Key West offers endless activities to make your trip unforgettable. Plan your trip around vibrant festivals like Fantasy Fest and Hemingway Days.

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Ready to start your Key West adventure?

Let us help you find the perfect rental and plan your unforgettable trip to paradise.

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  • Key West Business Guild Logo
  • The Vacation Rental Travel Guide - Most Outstanding Award for 2017
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  • AirBnB Super Host Badge
  • Vrbo Premier Host Badge