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.

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Displaying 36 - 40 of 45 results matching your search criteria

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Bahamian Rhapsody

Monthly and Seasonal Rentals

2 Bedrooms

2 Bathrooms

Comfortably Sleeps 4

Max Occupancy 4

This impeccably renovated property makes the perfect vacation getaway. At first glance, you can confirm its aesthetic appeal and secluded location half a block from Key West's celebrated Duval Street. If two bedrooms, two-and-a-half baths, an outstanding pool and deck area, and dedicated parking meet your...

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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...

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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...

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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...

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La Buena Vida

Monthly and Seasonal Rentals

2 Bedrooms

2 Bathrooms

Comfortably Sleeps 4

Max Occupancy 4

NEW UNIT!

Quintessentially Key West in terms of location and architecture, La Buena Vida won't disappoint as your next vacation rental. In fact, you'll be delighted. The location is Old Town's Bahama Village, an artsy and cultural quarter offering some of the best attractions and restaurants...

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