Houses for Rent in Islamorada, FL

A charming 2-bedroom, 1-bath cottage just a stone's throw from the beach in downtown Islamorada. This well-maintained 1,093 sq. ft. home features an in-unit washer and dryer, and all utilities included. Enjoy walking to nearby attractions like Morada Bay and Florida Keys Brewing Co., all in a highly desirable neighborhood. Experience the laid-back Florida Keys lifestyle without the resort price tag!

This charming two-story home sleeps up to 12 guests and perfectly supports multigenerational living. The upper level features the main living quarters, while the ground floor boasts a two-bedroom, one-bath suite with a kitchenette and private entrance. Ideal for hosting long-term guests or creating a private space, this flexible layout embraces comfort and connection with unforgettable sunsets in the Keys. Totaling 1,800 sq ft, this rental offers a perfect blend of spacious entertainment and intimate family time.

This inviting 3-bedroom, 2-bath home features a fully fenced yard and ample parking for boats and trailers. Enjoy the large screened front patio, perfect for relaxing. Pet-friendly and move-in ready, this property offers comfort and convenience in a charming neighborhood. An optional HOA provides access to a nearby boat ramp, ideal for water enthusiasts.

Experience luxury living in this stunning 2-bedroom, 2-bathroom corner townhouse at Executive Bay Club. This spacious, fully furnished unit features updated interiors and access to a private beach, pool, and tennis courts. Enjoy breathtaking sunsets and the convenience of first-come, first-serve dockage. Located near Founder's Park, partake in a variety of activities, including the Nautical flea market. Rent includes basic cable; electric and water are tenant responsibilities. No pets allowed.

Enjoy island living in this luxurious 3-bed, 3-bath Islamorada home. This pet-friendly property boasts a heated pool and large screened porch. Situated on a quiet street with walkable access to a shared park, including a beach, dock, and boat ramp. Rent furnished or unfurnished for short or long term, with utilities included for short-term stays. Perfect for enjoying endless island adventures and beachside sunrises.

Experience the ultimate Keys lifestyle in this beautifully updated waterfront home featuring high-end appliances and vaulted ceilings. Enjoy direct bay access with a private dock that accommodates a 22-ft boat, perfect for water adventures. Impact doors and windows enhance safety and efficiency, while the nearby White Marlin Beach Home Owner Park offers a serene escape. Enjoy the luxury of coastal living in this charming and meticulously maintained property.

Enjoy life in this charming 2-bedroom, 1.5-bathroom townhouse-style condo, boasting a peek-a-boo ocean view from the master bedroom. This completely furnished retreat features a modern updated kitchen with quartz counters, an in-unit washer/dryer, and an oversized Smart TV. Residents can relax by the heated pool, unwind at the oceanfront BBQ area, or catch dinner from the fishing pier. The perfect getaway to experience the beauty of the Florida Keys!

This beautifully renovated 2-bed, 3-bath townhouse offers a stylish and comfortable living space, complete with a loft featuring twin beds for guests. Located in Executive Bay Club, residents enjoy fantastic amenities including tennis courts, a swimming pool, and a private beach with stunning bay views. Fully furnished and ready for annual rental, this property perfectly embodies the vibrant Keys lifestyle with everything needed for relaxation and recreation.

Nestled in the heart of the Keys, this 4-bedroom, 3-bathroom home offers a two-story design with seamless canal access, perfect for boating enthusiasts. Within reach of Miami and the famous Tiki Bar sandbar, it features a 70-foot dock on a double-wide canal. Ideal for fishing and water adventures, your stay includes a minimum 28-night rental. Enjoy stunning sunsets and local dining, with boat rentals and a nearby marina for convenience.

This luxurious 3-bed, 2-bath Islamorada home offers stunning ocean views and direct canal access, perfect for boating enthusiasts. Featuring granite countertops, stainless steel appliances, and wood flooring, it epitomizes coastal elegance. Enjoy the Florida Keys lifestyle from your balcony while taking in the ocean breeze. Embrace island living with this dream retreat!