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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 21 - 25 of 40 results matching your search criteria
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Poinciana House

Nightly and Weekly Rentals
1 Bedroom
2 Bathrooms
Comfortably Sleeps 2
Max Occupancy 4

Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging back...

Conch in Training

Nightly and Weekly Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 4

The name of this one-bedroom, one full bath condo suggests the most persistent legend of Key West: that vacationers come for a week and stay a lifetime. Located in the prestigious gated Truman Annex community, this unit is the perfect place to try out island living...

Paradise Grand

Monthly and Seasonal Rentals
5 Bedrooms
4 Bathrooms
Comfortably Sleeps 10
Max Occupancy 10

Experience paradise in sumptuous style. That's what Paradise Grand, a breath-taking yet comfortable five-bedroom, four-bath estate, is all about. The house and private grounds and off-street parking occupy a whole city block of historic Old Town, exceptional spaciousness on the small island of Key West. Copious...

Azure Daydream

Monthly and Seasonal Rentals
4 Bedrooms
3 Bathrooms
Comfortably Sleeps 8
Max Occupancy 8

Great bones. Fascinating history. Outstanding location. With four bedrooms, three baths, and a private pool oasis, the home named Azure Daydream is the first-class ticket for your next vacation. More than a century ago, the residence was cut in half and moved by mules to its...

Coral Rock Retreat

Monthly and Seasonal Rentals
3 Bedrooms
3 Bathrooms
Comfortably Sleeps 8
Max Occupancy 8

How do you achieve vacation relaxation in a buzzing town like Key West? Look no further than Coral Rock Retreat, a conch house that promotes a mellow sensibility while still locating you very close to every fabulous thing that's happening on the coral rock that is...

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