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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Hilltop Hideaway

Monthly and Seasonal Rentals

2 Bedrooms

1 Bathroom

Comfortably Sleeps 4

Max Occupancy 4

APRIL STILL OPEN!

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...

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La Isla Vita

Monthly and Seasonal Rentals

2 Bedrooms

2 Full - 1 Half Bathrooms

Comfortably Sleeps 4

Max Occupancy 4

NEW UNIT!

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...

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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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Anne's Hideaway

Monthly and Seasonal Rentals

2 Bedrooms

2 Bathrooms

Comfortably Sleeps 4

Max Occupancy 4

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 modern functionality. The pool and...

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Bahamian Rhapsody

Monthly and Seasonal Rentals

2 Bedrooms

2 Full - 1 Half Bathrooms

Comfortably Sleeps 4

Max Occupancy 4

MARCH & APRIL STILL OPEN!

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,...

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