Islamorada Vacation Rentals - 50 Rentals Available

Relish ocean serenity in this residence set directly on a secluded beach, where an open-concept design seamlessly merges the living area and gourmet kit

Beds: 4 Baths: 4 Sleep: 12

Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish captivating tranquility with an o

Beds: 3 Baths: 2 Sleep: 10

This grand peninsula retreat, embraced by the Ocean and lush mangroves offering utmost privacy, has been designed for ultimate vacationing. Nestled alon

Beds: 5 Baths: 4 Sleep: 12

Relish ocean serenity in this residence set directly on a secluded beach, where an open-concept design seamlessly merges the living area and gourmet kit

Beds: 3 Baths: 3 Sleep: 10

Hidden in the heart of Islamorada, this oceanfront villa offers an unmatched privilege of a secluded private beach—an experience few can claim. Expans

Beds: 6 Baths: 4 Sleep: 16

This quaint Keys-style home offers timeless charm in a premier waterfront setting on an ocean-access canal. The open-concept living, kitchen, and dining

Beds: 3 Baths: 2 Sleep: 10

Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish captivating tranquility with a gr

Beds: 5 Baths: 3 Sleep: 14

Indulge in the epitome of coastal living in these two connected expansive duplex penthouses boasting ocean views in Islamorada. Relish captivating tranq

Beds: 8 Baths: 5 Sleep: 24

Premium extra large two bedroom, two bathrooms with very large living room, wet bar, large kitchen with dining area, private patio, a king size bed,

Beds: 2 Baths: 2 Sleep: 8

These are pictures of our Deluxe Penthouse Apartment, which does split in half with 2 double doors to create 2 seperate, smaller apartments. The fron

Beds: 2 Baths: 2 Sleep: 4