Places to Stay in Islamorada
Islamorada offers a range of lodging from luxury resorts to cozy vacation rentals.
Amara Cay Resort
Luxury waterfront resort with a private beach and marina. One of Islamorada's premier accommodations with upscale rooms, pools, and ocean views.
Playa Largo Resort
An upscale resort with full amenities including a private beach, multiple pools, waterfront dining, and a full-service spa. One of the most luxurious options in the Upper Keys.
Cheeca Lodge and Spa
An iconic Islamorada resort with a private beach, fishing pier, championship golf course, and full-service spa. Cheeca Lodge has been a landmark destination in the Keys for decades.
Islander Resort
A family-friendly resort with a beach, multiple pools, and a lively tiki bar. A great mid-range option that puts you right on the water with all the amenities you need.
Pelican Cove Resort
A waterfront resort with marina access. Perfect for boaters who want to dock right outside their room and enjoy the sunset over Florida Bay.
Marina Del Mar
A marina resort with dock access, perfect for boaters who want to tie up for the night. Centrally located near Islamorada's dining and attractions.
Vacation Rentals and Airbnbs
Numerous vacation rentals and Airbnb options are available across Islamorada's six islands. From canal-front homes with docks to cozy cottages, rentals give you the space and privacy of a home base while you explore the Keys.
Islamorada Vacation Rental Rules
The Village of Islands enforces some of the strictest short-term rental laws in Monroe County. Single-family homes in residential zones generally require a 28-day minimum stay. Vacation rentals under 28 days are restricted to specific commercial/hotel zones or properties with grandfathered licenses. Planning to invest in a vacation rental? Contact our team to view properties in designated zones that permit weekly or daily rentals.
Ready to make Islamorada your home?
Explore our Islamorada Community Guide to browse available homes and learn more about living here.
Planning a visit to Islamorada?
Contact Steve Conley for recommendations.
Love Islamorada? Explore our Islamorada Community Guide to browse available homes and learn more about living here.
Conley Sales Group is a real estate Team affiliated with Compass. Compass Florida, LLC d/b/a Compass is a licensed real estate broker and abides by equal housing opportunity laws. All material presented herein is intended for informational purposes only. Equal Housing Opportunity.