Chesapeake Resort

The Chesapeake Resort in Islamorada offers visitors to the Florida Keys a wonderful respite amidst heavenly surroundings and a private beach.  You don’t have to drive far to reach Paradise, and with the Chesapeake Resort, you’re there in less than two hours from Miami International Airport.

Chesapeake Resort is located on the Ocean side of Islamorada, so you get fabulous views from the water view rooms and villas.  The beach is gorgeous, and grounds are newly renovated, as are the rooms.  Families or groups can feel the comforts of home while on tropical vacation in one of thirteen villas equipped with full kitchens, splendid bathrooms and plenty of space to stretch out and live your dream vacation.

Step out onto your private terrace if you choose a villa, or even if you opt for one of 44 guest rooms or 8 suites in the main building.  Large HDTVs in rooms are new, and phones have data ports in case you don’t want to leave the real world entirely behind you while you’re in Islamorada.

After a day of water sports, charter fishing that leaves from the private Chesapeake Resort docks, or just lazing on the beach, you can enjoy the oceanfront hot tub or heated swimming pools.  Or how about watching the night sky from a Tiki hut observation deck?  We think you’ll agree the newly renovated Chesapeake Resort is better than ever!