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 31 - 35 of 39 results matching your search criteria

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La Buena Vida

Monthly and Seasonal Rentals

2 Bedrooms

2 Bathrooms

Comfortably Sleeps 4

Max Occupancy 4

MAY STILL OPEN!

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...

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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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La Isla Vita

Monthly and Seasonal Rentals

2 Bedrooms

2 Full - 1 Half Bathrooms

Comfortably Sleeps 4

Max Occupancy 4

Here's how to craft a perfect vacation. First, buy tickets to fabulous Key West. Second, shop for flipflops and shorts. Third, reserve La Isla Vita for your stay! This two-story, two-bedroom, three-bath home offers what you'd expect and then some. The "then-some" starts with private off-street...

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La Hacienda

Monthly and Seasonal Rentals

2 Bedrooms

2 Bathrooms

Comfortably Sleeps 4

Max Occupancy 4

MAY STILL OPEN!

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...

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Anne's Hideaway

Monthly and Seasonal Rentals

2 Bedrooms

2 Bathrooms

Comfortably Sleeps 4

Max Occupancy 4

MAY & JUNE STILL OPEN!

For luxurious vacation living, dining, sleeping, and playing, this historic Conch Home on fashionable Southard Street in the heart of Old Town hits the bullseye. It has been totally renovated, keeping its original cottage essence while adding contemporary design updates and...

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