Houses for Rent in Islamorada, FL

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.

This unfurnished 2-bedroom, 1-bathroom home features an updated kitchen and bath, central air, and wheelchair accessibility. Enjoy a large fenced yard and patio, perfect for outdoor gatherings. With convenient in-unit laundry, ample storage, and peaceful surroundings, this cozy retreat offers comfort and functionality. Utilities not included. Available for rent at $3,600/month starting October 9th, 2025.

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.

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 beautifully furnished 3-bedroom, 3-bathroom residence offers a spacious living and dining area with vaulted ceilings, providing a stylish yet functional atmosphere. Enjoy tranquility on two oversized porches, while covered parking adds convenience. Located off a private road, this home ensures privacy yet is a short stroll from downtown amenities, including local restaurants and shops, plus easy access to a private oceanfront beach. Perfect for comfortable Florida living!

This charming 3-bedroom, 3-bath home blends comfort and style perfect for long-term living. Enjoy an updated kitchen and spacious living area that opens to a large covered porch. The expansive primary suite occupies the entire third floor, featuring a private porch and walk-in closet. Located at Mile Marker 82, convenient access to shops, restaurants, and a neighborhood beach makes this home ideal for enjoying the best of Islamorada living.

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!

Discover affordable island living in this appealing 2-bedroom, 2.5-bath townhouse rental. Available through Habitat for Humanity of the Upper Keys, this residence requires Monroe County residency, specific income guidelines, and a credit score of 650+. Monthly rent is $2,149 plus utilities, with security deposit and first month's rent due at move-in. Pet restrictions apply.