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Key West Vacation Rentals

Browse the best rentals in Key West

Vacation rentals in Key West are perfect places to experience this special island. Every Key West rental has its own distinct charm. As one of Key West’s first property management companies, we represent some of the best rentals in Key West’s diverse communities. Many of our historic homes, villas, and condos come complete with private pools and beautiful outdoor areas that are great for singles, couples and families alike. We work closely with our guests to ensure that you receive personal service throughout your Key West Vacation.

Book a Dream Vacation to Key West today!

Displaying 36 - 40 of 44 results matching your search criteria
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Azure Hideaway

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 6
Max Occupancy 8

So you've decided to become one of those lucky enough to be vacationing in extraordinary Key West this year! Your next step is to choose just the right residence. With two plus bedrooms, two full baths, and a stellar location, Azure Hideaway could easily be your...

Hemingway's Cottage

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

NEW UNIT!

Soak it all up. The history. The ideal location. The expansive front porch and private pool oasis in back. Because of its proximity to the Ernest Hemingway House Historic Landmark, this two-bedroom, two-bath residence is aptly named "Hemingway's Cottage." Its location in the very...

En Plein Air

Monthly and Seasonal Rentals
2 Bedrooms
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 4

En Plein Air is a property that was purchased by the owners for its heritage and natural light. An artist lives here in this former general store. Recently renovated, it remains sympathetic to its 1880s roots. All the rooms have ceiling fans and air conditioners. Modern...

Hilltop Hideaway

Monthly and Seasonal Rentals
2 Bedrooms
1 Bathroom
Comfortably Sleeps 4
Max Occupancy 4

Hilltop Hideaway is near the top of Solares Hill, the highest point in Key West, a mere 15 feet above sea level. ("Hilltop" is a word the locals use loosely in Key West!) This meticulously cared for two-bedroom, one full bath condo is near the center...

La Hacienda

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

Looking as though it were plucked from the glossy pages of Spanish literature, La Hacienda is one of Key West's most distinctive two bedroom/two bath homes. Located on fashionable Southard Street in the heart of Old Town, the first thing you notice as you arrive is...

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