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4+ Bedroom Key West Rentals

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Truman House

Nightly and Weekly Rentals
4 Bedrooms
3 Bathrooms
Comfortably Sleeps 8
Max Occupancy 10

Early Bird Summer/Fall Specials! This unit is available for monthly rental only, during select summer into fall months at a BIG Savings. Please see the rate tab under the unit page for details, or call our office!!

The Keys have some of the most charming, top-rated...

Admiral's Lane

Nightly and Weekly Rentals
4 Bedrooms
3 Bathrooms
Comfortably Sleeps 8
Max Occupancy 8

As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old...

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...

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...

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...