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 16 - 20 of 39 results matching your search criteria

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Valhalla

Nightly and Weekly Rentals

2 Bedrooms

2 Bathrooms

Comfortably Sleeps 4

Max Occupancy 4

This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special...

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Rose Treehouse

Nightly and Weekly Rentals

1 Bedroom

1 Bathroom

Comfortably Sleeps 2

Max Occupancy 2

Classic Key West style defines this two-story Bahamian Colonial tucked away on Rose Lane, which runs only one block in its entirety, from Simonton to Duval. Rose Treehouse is a charming King bed, one-full-bath studio that occupies the whole second floor with balconies off both the...

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Campbell Suite

Nightly and Weekly Rentals

1 Bedroom

1 Full - 1 Half Bathrooms

Comfortably Sleeps 2

Max Occupancy 2

Let your rendezvous with paradise begin at the Campbell Courtyard compound in the heart of Old Town Key West. Campbell Suite, a second & third floor condo with one bedroom and 1½ baths, is the perfect place to anchor your vacation. It starts with the white...

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The Courtyard

Nightly and Weekly Rentals

1 Bedroom

1 Bathroom

Comfortably Sleeps 2

Max Occupancy 2

Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can step off your front porch and up to the deck of the enticing, heated, residents-only Monaco pool. Steps to the right, you'll find a raised deck with table, chairs,...

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Ann Street Gardens

Nightly and Weekly Rentals

1 Bedroom

1 Bathroom

Comfortably Sleeps 2

Max Occupancy 3

The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens offers the quintessential indoor/outdoor vacation experience you've come...

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